著者

小林 和弘 織田 範一 伊藤 磯雄

出版者

公益社団法人 日本薬学会

雑誌

YAKUGAKU ZASSHI (ISSN:00316903)

巻号頁・発行日

vol.101, no.9, pp.806-813, 1981-09-25 (Released:2008-05-30)

参考文献数

14

被引用文献数

1 1

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As the initial study of variations of skeletons of antitumor antibiotics, simple synthesis of naphtho [2, 3-g] quinolines (IIIa, b, VIII) and naphtho [2, 3-g] quinoxalines (XIIIa, b), which are novel heterocyclic ring systems, was carried out by Diels-Alder reaction of 1, 2-dimethylenecyclohexane with quinoline-5, 8-diones (Ia-c) or quinoxaline-5, 8-diones (IIa, b). Air oxidation of these Diels-Alder adducts gave tetrahydro naphtho [2, 3-g] quinolines (IVa, b, IX) and tetrahydronaphtho [2, 3-g] quinoxalines (XVa, b). The Diels-Alder adducts and aromatized compounds were converted into the corresponding diacetoxynaphtho [2, 3-g] quinolines (VI, VII, X) and diacetoxynaphtho [2, 3-g] quinoxalines (XVII, XVIII).

著者

小林 和弘 織田 範一 榊原 仁作

出版者

公益社団法人 日本薬学会

雑誌

YAKUGAKU ZASSHI (ISSN:00316903)

巻号頁・発行日

vol.103, no.2, pp.165-172, 1983-02-25 (Released:2008-05-30)

参考文献数

16

被引用文献数

1 1

---

Ethyl 5-hydroxybenzo [α] phenazine-6-carboxylates (IIa, b) were prepared by the condensation of ethyl 1, 4-dihydro-1, 4-dioxo-3-methoxy-2-naphthoate (I) with o-phenylene-diamines. Acylations and alkylations of IIa, b gave the corresponding o-acyl and alkyl compounds (IIIa-k). The reaction of IIa, b with ethanolamine gave β-hydroxyethyl-carboxamides (Va, b). Compound Va was converted into β-chlorinated compound (VIa), whose chlorine was substituted by dialkylamines to give ethylenediamine-type amides (VIIa, b, c). Compounds VIId and VIIe were obtained by the reaction of IIb with dialkylalkylenediamines. Oxidation of IIa, b afforded N-oxides (IXa, b). The antimicrobial activities of all synthetic compounds were tested by paper discagar diffusion assay. Compounds IIId, e, g, VIIa and IXa showed inhibitory activities to T. interdigitale and IXa to C. albicans.

著者

小林 和弘 織田 範一 榊原 仁作

出版者

公益社団法人 日本薬学会

雑誌

YAKUGAKU ZASSHI (ISSN:00316903)

巻号頁・発行日

vol.103, no.4, pp.473-479, 1983-04-25 (Released:2008-05-30)

参考文献数

8

被引用文献数

1 1

---

Ethyl 1, 4-dihydro-1, 4-dioxo-3-methoxy-2-naphthoate (I) is condensed with amidines, 2-aminopyridines and 3-aminopyrazole, to give new tetracyclic quinones (IIIa-c and VI) containing nitrogen atom and hydrogenation of IIIa and IIIb over Pd-C or Raney-Ni afforded 1, 2, 3, 4-tetrahydro (IXa, b) or 1, 2, 3, 4, 7, 8, 9, 10-octahydrobenzo[g]pyrido[2, 1-b]quinazoline (Xa), respectively. Benzo[g]pyrido[2, 1-b]quinazoline derivatives except for Xa showed inhibitory activities to S. aureus and T. interdigitale.

著者

織田 範一 小林 和弘 植田 泰誠 伊藤 磯雄

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.26, no.8, pp.2578-2581, 1978-08-25 (Released:2008-03-31)

被引用文献数

1 3

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Diels-Alder reaction of 5-nitro-1, 4-naphthoquinone (1) and unsymmetrical butadienes was carried out. Reaction of 1 and 2-methyl-1, 3-butadiene gave 1, 4, 4a, 9a-tetrahydro-2-methyl-5-nitro-anthraquinone (2) and its 3-methyl analogue (3) at the ratio of 9.2 : 1. Reaction of 1 and 1, 3-pentadiene gave 1, 4, 4a, 9a-tetrahydro-1-methyl-8-nitroanthraquinone (8) and its 5-nitro analogue (9) at the ratio of 10 : 7. Their structures have been determined by aromatization to methyl-nitroanthraquinones.

著者

小林 和弘 織田 範一 榊原 仁作

出版者

公益社団法人日本薬学会

雑誌

薬学雑誌 (ISSN:00316903)

巻号頁・発行日

vol.103, no.2, pp.p165-172, 1983-02

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Ethyl 5-hydroxybenzo [α] phenazine-6-carboxylates (IIa, b) were prepared by the condensation of ethyl 1,4-dihydro-1,4-dioxo-3-methoxy-2-naphthoate (I) with o-phenylene-diamines. Acylations and alkylations of IIa, b gave the corresponding o-acyl and alkyl compounds (IIIa-k). The reaction of IIa, b with ethanolamine gave β-hydroxyethyl-carboxamides (Va, b). Compound Va was converted into β-chlorinated compound (VIa), whose chlorine was substituted by dialkylamines to give ethylenediamine-type amides (VIIa, b, c). Compounds VIId and VIIe were obtained by the reaction of IIb with dialkylalkylenediamines. Oxidation of IIa, b afforded N-oxides (IXa, b). The antimicrobial activities of all synthetic compounds were tested by paper discagar diffusion assay. Compounds IIId, e, g, VIIa and IXa showed inhibitory activities to T. interdigitale and IXa to C. albicans.