 | OUCHI HidekazuDepartment of Pharmacy Professor/Manager | ||
Last Updated :2023/12/05
Researcher Information
Degree
J-Global ID
Research Interests
- 薬学教育 薬化学 有機合成化学 Medicinal Chemistry Heterocyclic Chemistry Synthetic Organic Chemistry
Research Areas
Academic & Professional Experience
- 2013/04 - Today Kinki UniversityFaculty of PharmacyProfessor
- 2009/04 - 2013/03 Aomori UnivetsityFaculty of PharmacyProfessor
- 2007/04 - 2009/03 Aomori UnivetsityFaculty of PharmacyAssociate Professor
- 2006/04 - 2007/03 Aomori UnivetsityFaculty of PharmacyAssociate Professor
- 2005/04 - 2006/03 Aomori UnivetsityFaculty of PharmacyLecturer
- 2005/02 - 2005/03 Tohoku Pharmaceutical UniversityFaculty of PharmacyLecturer
- 1995/04 - 2005/01 Tohoku Pharmaceutical UniversityFaculty of PharmacyAssistant Professor
Education
- - 1995 東北薬科大学 薬学研究科 薬化学
- - 1995 Tohoku Pharmaceutical University Graduate School, Division of Pharmaceutical Sciences
- - 1990 東北薬科大学 薬学部 製薬
- - 1990 Tohoku Pharmaceutical University Faculty of Pharmaceutical Science
Association Memberships
Published Papers
- Toshiro Noshita; Tatsuya Sato; Takahito Iwayama; Yohei Yamada; Hidekazu OuchiNatural Product Research Informa UK Limited 35 (21) 3787 - 3793 1478-6419 2021/11 [Refereed]
- Toshiro Noshita; Kentaro Fujita; Takeru Koga; Hidekazu Ouchi; Akihiro TaiBioorganic & Medicinal Chemistry Letters Elsevier BV 31 127674 - 127674 0960-894X 2021/01 [Refereed]
- Toshiro Noshita; Yusuke Kakizoe; Satoshi Tanabe; Hidekazu Ouchi; Akihiro TaiLetters in Organic Chemistry Bentham Science Publishers Ltd. 17 (12) 939 - 943 1570-1786 2020/12 [Refereed]
Extracts of Carolina jasmine (Gelsemium sempervirens (L.) J.St.-Hil.) petals were evaluated in vitro for inhibition activity against protein tyrosine phosphatase 1B (PTP1B). The principle active agent was also isolated from the extract and identified as ursolic acid (1). This is the first report of ursolic acid from G. sempervirens and of PTP1B-inhibiting activity in the genus Gelsemium. - Noshita Toshiro; Onishi Ryoya; Miura Kaori; Hamada Yoshitomo; Nishino Yuki; Ouchi Hidekazu; Tai AkihiroPHYTOCHEMISTRY LETTERS 27 214 - 218 1874-3900 2018/10 [Refereed]
- Tasuku Akiyama; Tsugunobu Andoh; Eiji Ohtsuka; Hiroshi Nojima; Hidekazu Ouchi; Hiroki Takahata; Yasushi KuraishiEuropean Journal of Pharmacology Elsevier B.V. 833 44 - 49 1879-0712 2018/08 [Refereed]
The antipruritic activity of gabapentin, an anticonvulsant, was studied in a mouse model of allergic itch. In mice sensitized by an extract of the salivary glands of the mosquito (ESGM), an intradermal injection of ESGM elicited scratching and increased peripheral nerve firing. Oral or intradermal administration of gabapentin at the ESGM injection site inhibited ESGM-induced scratching and peripheral nerve firing. However, gabapentin did not affect histamine-induced scratching. The distributions of immunoreactivity to the voltage-dependent calcium channel α2δ-1 subunit, a site of gabapentin action, and the histamine H1 receptor differed in the mouse dorsal root ganglia. The α2δ-1 subunit was mainly found in neurons that were 15–20 µm in diameter, whereas the H1 receptor was mainly in 20–30 µm neurons. In addition, α2δ-1 subunit immunoreactivity co-localized with that of transient receptor potential vanilloid 1 (TRPV1). These results suggest that gabapentin regulates allergic itch by acting on the calcium channel α2δ-1 subunit in peripheral TRPV1-positive neurons. - Toshiro Noshita; Kaori Miura; Kaoru Ikeda; Hidekazu Ouchi; Takuya Matsumoto; Akihiro TaiJournal of Natural Medicines Springer Tokyo 72 (2) 551 - 556 1861-0293 2018/03 [Refereed]
The incidence of type I allergies, which are associated with mast cell degranulation and local inflammation, is increasing, and new treatments are needed. To date, structure–activity relationships of flavonoids in their degranulation-inhibiting activity have not been systematically characterized. In the current study, the degranulation-inhibiting activity of a series of flavonoids was evaluated. The following three observations were made: (1) the activity disappears when a sugar moiety is introduced into the A ring of the flavanone (2) the activity depends on the number of hydroxyl groups on the B ring (3) the activity is markedly enhanced when a double bond is introduced into the C ring. The information obtained in the current study may guide the development of a therapy for type I allergies. - Toshiro Noshita; Kohei Matsumoto; Hikaru Nishikawa; Hidekazu Ouchi; Yoshitomo Hamada; Akiko Saito; Teiko YamadaNATURAL PRODUCT RESEARCH TAYLOR & FRANCIS LTD 31 (2) 163 - 168 1478-6419 2017 [Refereed]
We describe the synthesis of 4,4'-oxyneolignan, the proposed structure for naturally occurring apteniol D. The diphenyl ether moiety in 4,4'-oxyneolignan was formed via classical Ullmann ether synthesis using excess copper powder in N,N-dimethylacetamide. The spectral data of synthesised apteniol D show differences compared to those of naturally occurring apteniol D. [GRAPHICS] . - Shunji ISHIWATA; Atsushi TAGA; Fumihiko OGATA; Manabu KITAKOUJI; Hidekazu OUCHI; Hirokuni YAMANISHI; Masayo INAGAKIJournal of Smart Processing Smart Processing Society for Materials, Environment & Energy (High Temperature Society of Japan) 4 (6) 294 - 297 2186-702X 2015/06 [Refereed]
Radioactive cesium has strongly bound soil as time proceeded, which could not be cleaved in mild condition. We have found that serial treatment of ammonium citrate solution and ionic liquid removed radioactive cesium from soil effectively. The sequence of the treatment is crucial, since inverse serial treatment or mixture of two kinds of solution did not show such an effect, which suggested that ammonium citrate unlocked trapped cesium in soil and ionic liquid solved it. We also found that repeating serial treatment and prolonged treatment time additively removed cesium from soil. - Toshiro Noshita; Akihiro Tai; Hikaru Nishikawa; Kaoru Ikeda; Hidekazu Ouchi; Yoshitomo Hamada; Akiko Saito; Teiko YamadaBIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY TAYLOR & FRANCIS LTD 79 (11) 1743 - 1749 0916-8451 2015 [Refereed]
The synthesis of compounds with the structures proposed for the oxyneolignan apteniols B, C, and G is described. The diphenyl ether skeletons of the proposed apteniols were formed via Ullmann ether synthesis. In particular, the spectral data for the synthesized apteniols B, C, and G did not agree with those previously reported for the isolated compounds. Furthermore, the synthesized proposed apteniol B did not show degranulation-inhibiting activity, while the prepared proposed apteniols C and G exhibited activities considerably weaker than that of the methyl ester of proposed apteniol A. - Hikaru Nishikawa; Toshiro Noshita; Akihiro Tai; Hidekazu Ouchi; Taisuke Okamoto; Akiko Saito; Teiko Yamada; Atsuko Iomori; Nao IshimataBIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY TAYLOR & FRANCIS LTD 78 (9) 1485 - 1489 0916-8451 2014/09 [Refereed]
We describe the syntheses of the proposed structure of diphenyl ether oxyneolignan, apteniol A and its derivatives. The diphenyl ether moiety of proposed apteniol A was formed via Ullmann ether synthesis, but the spectral data of the synthesized apteniol A did not agree with that in previous studies. The dimethyl ester derivative of the proposed apteniol A was found to enhance neurite outgrowth in PC12 cells and inhibit antigen-induced degranulation in RBL-2H3 cells. - Yukako Saito; Hidekazu Ouchi; Hiroki TakahataTETRAHEDRON PERGAMON-ELSEVIER SCIENCE LTD 64 (49) 11129 - 11135 0040-4020 2008/12 [Refereed]
Formation of carboxamides of a variety of carboxylic acids with the coupling reagent BBDI is described, This procedure permits a one pot and simple operation without the need of any bases and no base was required for even use of amine hydrochlorides. In addition, an approach to BBDI-catalyzed carboxamidation is examined. (C) 2008 Elsevier Ltd. All rights reserved. - Yukiko Mihara; Hidetomo Ojima; Tatsushi Imahori; Yuichi Yoshimura; Hidekazu Ouchi; Hiroki TakahataHETEROCYCLES PERGAMON-ELSEVIER SCIENCE LTD 72 (1) 633 - 645 0385-5414 2007/04 [Refereed]
The asymmetric synthesis of all stereoisomers of isofagornine from 5-hydroxymethyl-3-piperidene 6, which was prepared by [2,3]-Wittig rearrangement of O-alkylstannylmethyl compound 5 derived from readily available chiral 3-hydroxypiperidene 4, is described. - Hiroki Takahata; Yurniko Suto; Erina Kato; Yuichi Yoshimura; Hidekazu OuchiADVANCED SYNTHESIS & CATALYSIS WILEY-V C H VERLAG GMBH 349 (4-5) 685 - 693 1615-4150 2007/03 [Refereed]
The palladium-catalyzed deracemization of N-protected alkyl carbonates of 5-hydroxy-3-piperidenes by use of chiral phosphine ligands is described. A Trost ligand such as (R)-BPA was found to be a suitable chiral ligand for the deracemization, providing N-protected 5-hydroxy-3-piperidenes in good yields with good to high enantioselectivities. A plausible mechanism for the reaction is proposed. - Yukako Saito; Hidekazu Ouchi; Hiroki TakahataTETRAHEDRON PERGAMON-ELSEVIER SCIENCE LTD 62 (50) 11599 - 11607 0040-4020 2006/12 [Refereed]
The use of 1-tert-butoxy-2-tert-butoxycarbonyl-1,2-dihydroisoquinoline (BBDI) as a tert-butoxycarbonylation reagent for acidic proton-containing substrates such as phenols, aromatic and aliphatic amines hydrochlorides, and aromatic carboxylic acids in the absence of a base is described. The reactions proceed chemoselectively in high yield under mild conditions. (c) 2006 Elsevier Ltd. All fights reserved. - Hidekazu Ouchi; Hisao Saito; Yutaka Yamamoto; Hiroki TakahataHeterocycles 66 (1) 299 - 308 0385-5414 2005/12 [Refereed]
The synthesis of novel poly-functionalized 5-acetoacetyl-3-acetyl-2-pyridone derivatives was achieved via the ring-transformation of 6-methyl-4H-1,3-oxazin-4-ones with 3-methylisoxazole derivatives, followed by reductive cleavage of the isoxazole ring and hydrolysis. © 2005 The Japan Institute of Heterocyclic Chemistry. - H Ouchi; Y Mihara; H TakahataJOURNAL OF ORGANIC CHEMISTRY AMER CHEMICAL SOC 70 (13) 5207 - 5214 0022-3263 2005/06 [Refereed]
A new general method for the synthesis of a variety of 1-azasugars with a nitrogen atom at the anomeric position is described. The readily available chiral N-Boc-5-hydroxy-3-piperidene 3 is transformed to isofagomine (2), homoisofagomine (13), and 5'-deoxyisofagomine (14) via stereo-selective epoxidation and regioselective ring-cleavage in a highly stereocontrolled manner. In addition, the synthesis of all four stereoisomers of 3,4,5-trihydroxypiperidines (18-21) classified as 1-azasugar-type glycosidase inhibitors was stereoselectively achieved from the (chiral) piperidene 3. - A Kato; N Kato; E Kano; Adachi, I; K Ikeda; L Yu; T Okamoto; Y Banba; H Ouchi; H Takahata; N AsanoJOURNAL OF MEDICINAL CHEMISTRY AMER CHEMICAL SOC 48 (6) 2036 - 2044 0022-2623 2005/03 [Refereed]
L-Enantiomers of 1-deoxynojirimycin (DNJ), 1-deoxymannojirimycin (manno-DNJ), 1-deoxyallonojirimycin (allo-DNJ), 1-deoxyaltronojirimycin (altro-DNJ), 1-deoxygalactonojirimycin (galacto-DNJ), 1-deoxygulonojirimycin (gulo-DNJ), and 1-deoxyldonojirimycin (ido-DNJ) were prepared according to prior methods for the D-enantiomers. These enantiospecific syntheses established unambiguously the absolute configuration of naturally occurring DNJ, manno-DNJ, allo-DNJ, altro-DNJ, and gulo-DNJ. Although D-DNJ and D-galacto-DNJ are known to be powerful competitive inhibitors of alpha-glucosidase and alpha-galactosidase, respectively, with K-i values in the nM range, L-DNJ and L-galacto-DNJ were noncompetitive inhibitors of alpha-glucosidase and alpha-galactosidase, respectively, with K-i values in the PM range. However, the azasugar mimicking the structure of the terminal sugar moiety of the natural substrate is not always an inhibitor of the glycosidase responsible for the hydrolysis. D-manno-DNJ is known as a much better inhibitor of alpha-L-fucosidase than a-mannosidase, while L-allo-DNJ was a better inhibitor than D-manno-DNJ of alpha-mannosidase. L-galacto-DNJ can be regarded as the 6-hydroxylated derivative of deoxyfuconojirimycin (DFJ), which is a powerful inhibitor of alpha-L-fucosidase with a K-i value in the nM range. However, this replacement of the methyl group in DFJ by a hydroxymethyl group reduced its affinity by about 50-fold. This suggests that there is a hydrophobic region in or around the active site of alpha-L-fucosidase. It has been found that inhibitors of human lysosomal glycosidases have therapeutic potential for the corresponding lysosomal storage diseases (Nat. Med. 1999, 5, 112; Proc. Natl. Acad. Sci. USA, 2002, 99, 15428). Inhibition of human lysosomal glycosidases by the 1-deoxyazasugars synthesized was investigated. D-galacto-DNJ is a potent inhibitor of lysosomal alpha-galactosidase (IC50 = 90 nM) and is now being evaluated preclinically for its potential use in Fabry disease, while D-DNJ inhibiting alpha-glucosidase (IC50 = 40 nM) potently does not appear to become a potential therapeutic agent because of additional inhibitory activity toward glycoprotein processing alpha-glucosidases. On the other hand, although L-allo-DNJ is a moderate inhibitor of alpha-mannosidase (IC50 = 64 mu M), it may become a key compound for the drug design of potential therapeutic agents for alpha-mannosidosis. - Y Saito; T Yamaki; F Kohashi; T Watanabe; H Ouchi; H TakahataTETRAHEDRON LETTERS PERGAMON-ELSEVIER SCIENCE LTD 46 (8) 1277 - 1279 0040-4039 2005/02 [Refereed]
A very mild, one-step esterification using nearly equimolar amounts of N-protected amino acids and alcohols, in conjunction with 1-tert-butoxy-2-tert-butoxycarbonyl-1,2-dihydroisoquinoline (BBDI) as a novel condensing reagent is described. (C) 2005 Elsevier Ltd. All rights reserved. - N Asano; K Ikeda; L Yu; A Kato; K Takebayashi; Adachi, I; Kato, I; H Ouchi; H Takahata; GWJ FleetTETRAHEDRON-ASYMMETRY PERGAMON-ELSEVIER SCIENCE LTD 16 (1) 223 - 229 0957-4166 2005/01 [Refereed]
1,4-Dideoxy-1,4-imino-L-arabinitol (L-AB1) and 2,5-dideoxy-2,5-imino-L-mannitol (L-DMDP) are much more potent inhibitors of isomaltase than their D-enantiomers. D-Enantiomers inhibited isomaltase in a competitive manner. whereas L-enantiomers were noncompetitive inhibitors of the enzyme. Similarly D-isofagomine and L-isofagomine were competitive and noncompetitive inhibitors of human lysosomal beta-D-glucosidase (beta-glucocerebrosidase), with K-i values of 0.016 and 5.7 muM, respectively. The multiple inhibition analysis of beta-glucocerebrosidase by D-isofagomine and L-isofagomine indicated that the D-enantiomer best fits the catalysis site of beta-glucocerebrosidase. while the L-enantiomer has a favorable interaction with a regulatory site other than the active site. Our recent and present results suggest that D-iminosugars are competitive inhibitors Of D-glycohydrolases but their L-enantiomers are noncompetitive inhibitors. (C) 2004 Elsevier Ltd. All rights reserved. - H Ouchi; M Kumagai; S Sakurada; H TakahataHETEROCYCLES PERGAMON-ELSEVIER SCIENCE LTD 64 505 - 514 0385-5414 2004/12 [Refereed]
All possible regioisomers of dimethyl-substituted (S)-phenylalanine were efficiently synthesized by reacting the NI(Il)-complex of the chiral Schiff base of glycine with (S)-2-N-(N-benzylprolyl)aminobenzophenone. - H Ouchi; Y Mihara; H Watanabe; H TakahataTETRAHEDRON LETTERS PERGAMON-ELSEVIER SCIENCE LTD 45 (38) 7053 - 7056 0040-4039 2004/09 [Refereed]
A short and concise synthesis of isofagomine derivatives via the epoxidation of chiral N-Boc-5-hydroxy-3-piperidene, followed by regioselective epoxide ring opening is described. This constitutes the first reported synthesis of homoisofagomine and the 5'-deoxyisofagomine. (C) 2004 Elsevier Ltd. All rights reserved. - H Ouchi; Y Kawata; M Ono; Y Morita; Y Yamamoto; H TakahataHETEROCYCLES PERGAMON-ELSEVIER SCIENCE LTD 62 (1) 491 - 501 0385-5414 2004/01 [Refereed]
The novel synthesis of 6- or 7-aromatic substituted 2H-isoquinolin-1-ones, by two different routes is described. In the first route, 7-substituted derivatives were prepared by regioselective iodination at the 7-position of 6,8-dihydroxy-4-ethoxycarbonyl-2H-isoquinolin-1-one derivatives (1) followed by the Stille coupling reaction. In the second route, 6-subsutituted derivatives were prepared by the selective triflation of the 6-hydroxy group of 1 followed by the Stille coupling reaction. - Hidekazu OUCHI; Yoko KAWATA; Yasuo MORITA; Yutaka YAMAMOTO; Hiroki TAKAHATAJournal of Tohoku Pharmaceutical University Tohoku Pharmaceutical University 50 (50) 75 - 79 1345-157X 2003/12 [Refereed]
Reactions of 4H-1, 3-oxazin-4-ones with cyclic ketones such as α-tetralone, β-tetralone, and Δ^<1(9)>-octalone-2 afforded 9, 10-dihydrobenz [f] isoquinolin-3(2H)-ones, 5, 6-dihydrobenz- [h] isoquinolin-3(2H)-ones, and 6, 7, 8, 9, 10-pentahydrobenz [g] isoquinolin-3(2H)-ones, respectively. - H Takahata; Y Banba; H Ouchi; H NemotoORGANIC LETTERS AMER CHEMICAL SOC 5 (14) 2527 - 2529 1523-7060 2003/07 [Refereed]
[GRAPHICS] A concise and stereoselective synthesis of the chiral building block, dioxanylpiperidene 4 as a precursor for deoxyazasugars, starting from the Garner aldehyde 5 using catalytic ring-closing metathesis (RCM) for the construction of the piperidine ring is described. The asymmetric synthesis of 1-deoxygalactonojirimycin and its congeners 1-3 was carried out via the use of 4 in a highly stereocontrolled mode. - H Takahata; Y Banba; H Ouchi; H Nemoto; A Kato; Adachi, IJOURNAL OF ORGANIC CHEMISTRY AMER CHEMICAL SOC 68 (9) 3603 - 3607 0022-3263 2003/05 [Refereed]
The asymmetric synthesis of fagomine and its congeners 1-4 has been achieved by catalytic ring-closing metathesis (RCM). The synthesis involved the construction of the piperidene-type chiral building block 5 followed by dihydroxylation, starting from the D-serine-derived Garner aldehyde 6. - Y Kuraishi; Y Iida; HW Zhang; S Uehara; H Nojima; J Murata; Saiki, I; H Takahata; H OuchiBIOLOGICAL & PHARMACEUTICAL BULLETIN PHARMACEUTICAL SOC JAPAN 26 (4) 550 - 552 0918-6158 2003/04 [Refereed]
In this study, we examined whether several types of non-opioid agents would inhibit the pain-related responses of melanoma-bearing mice. Orthotopic inoculation with melanoma into the hind paw induced marked tactile allodynia and mechanical hyperalgesia. A peroral injection (p.o.) of gabapentin (100-300 mg/kg) inhibited the allodynia and hyperalgesia, without effects on gross behaviors. An intraperitoneal injection (i.p.) of ketamine hydrochloride (30 mg/kg) produced partial inhibition in allodynia and hyperalgesia and prostate posture at 15 min after injection. Diclofenac sodium (10 and 30 mg/kg, i.p), mexiletine hydrochloride (20 mg/kg, i.p.), clonidine hydrochloride (0.1 mg/kg, i.p.) and suramin (100 mg/kg, i.p.) were without effects on allodynia and hyperalgesia. Subcutaneous injections of baclofen (3 mg/kg) and N-G-nitro-L-arginine methyl ester (100 mg/kg) were also without effects. Repeated administration of gabapentin (150 mg/kg, p.o.) produced constant inhibitions, suggesting no analgesic tolerance. Gabapentin may be useful for the management of cancer pain. - H Takahata; H Ouchi; M Ichinose; H NemotoORGANIC LETTERS AMER CHEMICAL SOC 4 (20) 3459 - 3462 1523-7060 2002/10 [Refereed]
[GRAPHICS] C-2-Symmetric 2,6-diallyipiperidine 1-carboxylic acid methyl ester (5) was examined via the double asymmetric allylboration of glutaraldehyde followed by aminocyclization and carbamation as a promising chiral building block for piperidine-related alkaloids, which were synthesized by the desymmetrization of 5 using intramolecular iodocarbamation as a key step. - Akihiro Ambo; Harumi Murase; Hideko Niizuma; Hidekazu Ouchi; Yutaka Yamamoto; Yusuke SasakiBioorganic and Medicinal Chemistry Letters 12 (6) 879 - 881 0960-894X 2002/03 [Refereed]
The usefulness of 2,6-dimethylphenylalanine (Dmp) as a Phe surrogate in two opioid peptides, dermorphin (DM) and deltorphin II (DT), was investigated. Compared to DM, [L-Dmp3]DM (1) showed a 170-fold increase in μ affinity and only a 4-fold increase in δ affinity, resulting in a 40-fold improvement in μ receptor selectivity. Compared to DT, [L-Dmp3]DT (3) showed a 22-fold increase in δ affinity and somewhat of a loss in μ affinity, and consequently a marked (75-fold) improvement in δ receptor selectivity. The D-Dmp replacement, however, resulted in a great loss in receptor selectivity in each of the peptides. The specific receptor interactions of 1 and 3 were confirmed by in vitro bioassays. Analogues 1 and 3 seem to be useful as pharmacological tools for the study of opioid systems. © 2002 Elsevier Science Ltd. All rights reserved. - H Ouchi; Y Saito; Y Yamamoto; H TakahataORGANIC LETTERS AMER CHEMICAL SOC 4 (4) 585 - 587 1523-7060 2002/02 [Refereed]
[GRAPHICS] The use of 1-tert-butoxy-2-tertbutoxycarbonyl-1,2-dihydroisoquinoline (BBDI) as tertbutoxycarbonylation reagent for aromatic and aliphatic amine hydrochlorides and phenols in the absence of a base has been demonstrated. The reactions proceed chemoselectively in high yield under mild conditions. - Y Sasaki; M Hirabuki; A Ambo; H Ouchi; Y YamamotoBIOORGANIC & MEDICINAL CHEMISTRY LETTERS PERGAMON-ELSEVIER SCIENCE LTD 11 (3) 327 - 329 0960-894X 2001/02 [Refereed]
Four Leu-enkephalin (Enk) analogues containing 2'.6'-dimethyphenylalanine (Dmp) in position 4 were prepared and tested for their receptor binding and biological activities. Among the analogues prepared, [2', 6'-dimethvltyrosine(1), D-Dmp(4)]Enk was found to be an antagonist toward mu and delta opioid receptors with pA(2) values of 6.90 and 5.57, respectively. (C) 2001 Elsevier Science Ltd. All rights reserved. - Y Sasaki; T Suto; A Ambo; H Ouchi; Y YamamotoCHEMICAL & PHARMACEUTICAL BULLETIN PHARMACEUTICAL SOC JAPAN 47 (10) 1506 - 1509 0009-2363 1999/10 [Refereed]
To understand the effect of the replacement of Tyr residue at position 1 in opioid peptides by 2,6-dimethyl-Tyr (Dmt) on the biological property, chiral (D or L) Dmt(1) analogs of Leu-enkephalin (Enk) and Tyr-D-Arg-Phe-beta Ala-NH2 (YRFB) were synthesized and their enzymatic stabilities, irt vitro bioactivities and receptor binding affinities compared with those of parent peptides, [L-Dmt(1)]Enk (1) exhibited 4-fold higher stability against aminopeptidase-IM and possessed dramatically increased activities in guinea pig ilium (GPI) (187-fold) and mouse vas deferens (MVD) (131-fold) assays, and in rat brain receptor binding assays (356-fold at mu receptor and 46-fold at delta receptor) as compared to Enk [L-Dmt(1)]YRFB (3) also exhibited increased activities in GPI (46-fold) and MVD (177-fold) assays, and in the binding assays (69-fold at mu receptor and 341-fold at delta receptor) as compared to the parent peptide. [D-Dmt(1)]Enk (2) and [D-Dmt(1)]YRFB (4) exhibited activities with diminished or lesser potency than the parent peptide in all assays. These results indicate that there is a tendency for mu affinity to be enhanced more than delta affinity with introduction of L-Dmt into delta ligand peptide (Enk), and for delta affinity to be enhanced more than ill affinity in case of mu ligand peptide (YRFB), resulting in reduced receptor selectivities at the receptors. - Reactions of Di-tert-butyl Dicarbonate with Benzodiazines and Synthetic Applications of the ProductsHidekazu OUCHI; Yukako SAITO; Noriko Koriyama; Yutaka YAMAMOTOAnnual Report of Tohoku College of Pharmacy Tohoku Pharmaceutical University 45 (45) 111 - 116 0495-7342 1998/12 [Refereed]
- Y YAMAMOTO; H OUCHI; T TANAKA; Y MORITAHETEROCYCLES ELSEVIER SCIENCE BV 41 (6) 1275 - 1290 0385-5414 1995/06 [Refereed]
The reactions of acylformyl chlorides with 2- and 4-trimethylstannylpyrimidine derivatives proceeded more smoothly than those of acyl chlorides giving the corresponding 2- and 4-acylpyrimidines. Employing ethyl chlorogly-oxylate in stead of the acylating agent yielded the ethoxycarbonylpyrimidines. Similarly, the stepwise acylation and ethoxycarbonylation of bis(trimethylstannyl)-pyrimidines provided pyrimidines having two different carbon functional groups. - Y YAMAMOTO; H OUCHI; T TANAKACHEMICAL & PHARMACEUTICAL BULLETIN PHARMACEUTICAL SOC JAPAN 43 (6) 1028 - 1030 0009-2363 1995/06 [Refereed]
Alkoxycarbonylation and acylation at the a-position of pyridine, qninoline, and isoquinoline via the respective trimethylstannyl derivatives were satisfactorily performed by employing ethyl chloroglyoxylate and acylformyl chloride under mild conditions. - Y YAMAMOTO; H OUCHI; T TANAKACHEMICAL & PHARMACEUTICAL BULLETIN PHARMACEUTICAL SOC JAPAN 43 (6) 916 - 919 0009-2363 1995/06 [Refereed]
Di-tert-butyl dicarbonate was found to be effective for direct introduction of a tert-butoxycarbonyl group at the alpha-position of the pyridine nucleus via the trialkylstannyI group; reaction of d-trialkylstannyl derivatives of pyridine, quinoline, and isoquinoline with di-tert-butyl dicarbonate gave the corresponding alpha-tert-butoxycarbonyl derivatives in good yields, although small amounts of a variety of by-products were formed except in the case of pyridine. - Y YAMAMOTO; T TANAKA; H OUCHI; M MIYAKAWA; Y MORITAHETEROCYCLES ELSEVIER SCIENCE BV 41 (4) 817 - 825 0385-5414 1995/04 [Refereed]
Method for introduction of two types of carbon functional groups, acyl and tert-butoxycarbonyl groups, in pyridine ring via bis(trimethylstannyl) pyridine (1) is explored. Application of this method to the synthesis of fusaric add (11) is also described. - Yutaka YAMAMOTO; Hidekazu OUCHIAnnual Report of Tohoku College of Pharmacy Tohoku Pharmaceutical University 41 (41) 79 - 82 0495-7342 1994/12 [Refereed]
Books etc
- 大内秀一 (Single work)京都廣川書店 2016/03 4906992722 224
- これからはじめるIT活用術 (薬剤師の強化書)大内秀一; 安藤裕明; 丁元鎮; 和田育男 (Contributor構造式や反応式を簡単に書きたい)南山堂 2009/12 9784525788216
MISC
- 稲見俊伸; 野下俊朗; 大内秀一 日本農芸化学会中四国支部講演会講演要旨集(Web) 42nd- C‐7 (WEB ONLY) 2015/06
- Y Omori; T Andoh; H Ouchi; H Takahata; H Nojima; Y Kuraishi JOURNAL OF PHARMACOLOGICAL SCIENCES 97- 129P -129P 2005
- Takahata Hiroki; Ouchi Hidekazu; Banba Yasunori; Kato Atsushi; Adachi Isao; Asano Naoki 天然有機化合物討論会講演要旨集 (46) 467 -472 2004/10
- Takahata Hiroki; Mihara Yukiko; Ouchi Hidekazu; Banba Yasunori; Nemoto Hideo; Kato Atsushi; Adachi Isao 天然有機化合物討論会講演要旨集 (45) 419 -424 2003/09
- SASAKI Yusuke; AMBO Akihiro; MURASE Harumi; HIRABUKI Mariko; OUCHI Hidekazu; YAMAMOTO Yutaka Peptide science : proceedings of the ... Japanese Peptide Symposium 2000- 117 -120 2001/03
Research Grants & Projects
- Development of a participatory learning support system connecting basic knowledge of pharmaceutical sciences to clinicalJapan Society for the Promotion of Science：Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C)Date (from‐to) : 2018/04 -2021/03Author : 大内 秀一初年度の研究計画内容に準じて、専用のサーバー上にオープンソースのe-ラーニングプラットフォームの Moodle を利用して学修システムの構築を行った。問題基盤型学習 (Problem-Based Learning＝PBL) とチーム基盤型学習 (Team-Based Learning＝TBL)を教授者1名でも運用できるように、フォーラム機能（学生へのアナウンス、PBLおよびTBLでのグループ内のディスカッションの書き込み）、Wiki機能（PBLでのまとめ作成）、課題機能（プレゼン資料の提出）、フィードバック機能（Peer評価、アンケート）、ファイルおよびフォルダ機能（資料の提示）を組み合わせて、視覚的に分かりやすく配置した学修システムを構築した。 薬剤師国家試験を意識した問題をTBLで用いる問題として設定するため、1996年から2018年までの22年分の薬剤師国家試験に出題されている新薬の出題傾向をテキストマイニングの手法を用いて分析した。その結果、科目ごとの出題傾向を知ることができた。（この結果を、第68回 日本薬学会近畿支部総会・大会にて発表した。） PBLで用いるシナリオを作成するため、次の検討を行った。(1) 医薬品副作用データベース (JADER) を用いて機械学習による薬の副作用の予測について検討を行い、副作用の発現傾向を分析した。（この分析結果を、第28回日本医療薬学会年会にて発表した。）また、病院や薬局で実務実習を行った５年生の実務実習報告書の症例の中から８疾患（がん、高血圧症、糖尿病、心疾患、脳血管障害、精神疾患、免疫・アレルギー疾患、感染症）に関連する症例に絞って内容を精査した。
- 複素環化合物を利用した機能性試薬の開発Date (from‐to) : 2001
- Development of functional reagent using heterocyclic compoundDate (from‐to) : 2001
- 生体機能分子の合成および設計Date (from‐to) : 1998
- Study on synthesis and design of the bioactive moleculesDate (from‐to) : 1998