- Synthesis of a benzo[5,6]cyclohepta[1,2-b]thiophene and thieno[3,2-c]-benzazepine derivatives
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A new series of 2-methyl-4-(4-methylpiperazin-1-yl)-10H-benzo[5,6]cyclohepta[1,2-b]thiophene (5) and 2-methyl-4-(4-methylpiperazin-1-yl)thieno[3,2-c][1]benzazepine derivatives 6b - f have been synthesized from 2-methylthiophene and phthalic anhydride. Preparation of the key intermediate 2-methyl-4,5-dihydro-10H-benzo[5,6]cyclohepta[1,2-b]thiophene-4-one (12) and 2-methylthieno[3,2-c][1]benzazepine-4(5H), 10-dione (16) were carried out by intramolecular dehydration of the phenylacetic acid 11 and Lewis acid associated cyclization of the isocyanate 14, respectively.
- Kohara, Toshiyuki,Tanaka, Hiroshi,Kimura, Koreichi,Fujimoto, Tetsuya,Yamamoto, Iwao,Arita, Masafumi
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p. 355 - 360
(2007/10/03)
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- Cyclohepta[b]thiophene derivatives. Part-IV. Dehydrogenation of cyclohepta[b]thiophene and cyclohepta[c]thiophene derivatives
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Cyclohepta[b]thiophenes 3 and cyclohepta[c]thiophene 4 on dehydrogenation with selenium give a complex mixture of dehydrogenated products. The formation of the identified products is explained through the initial homolytic cleavage at more than one particular bond in the cycloheptane moiety of 3 and 4. In all these cases ring contraction of the seven-membered ring of the thiophenes 3 and 4 is observed.
- Lahiri, Sikha,Sen
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p. 209 - 212
(2007/10/03)
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- Novel antiasthmatic agents with dual activities of thromboxane A2 synthetase inhibition and bronchodilation. 1. 2-[2-(1-imidazolyl)alkyl]- 1(2H)-phthalazinones
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A number of 4-substituted 2-[ω-(1-imidazolyl)alkyl]-1(2H)-phthalazinones were synthesized in order to develop agents possessing both thromboxane A2 synthetase inhibitory and bronchodilatory activities. The pharmacological evaluation of these compounds disclosed that they have both activities to various extents. Both activities were slightly dependent on the length of the 2-substituents and largely affected by the nature of the 4-substituents. Compounds bearing phenyl and thienyl groups exhibited relatively high and well-rounded activities. Among these compounds, 12j and 15f were found to be the most effective agents having well-rounded activities in vitro and in vivo. Introduction of a carboxyl group reduced both activities contrary to our expectation. 4-(3-Pyridyl)phthalazinone 18b was of particular interest because of unexpectedly high in vivo activities in spite of an absence of significant in vitro activities.
- Yamaguchi,Kamei,Koga,Akima,Kuroki,Ohi
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p. 4052 - 4060
(2007/10/02)
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