Antibacterial effect of lichen substances and related compounds VI. Dibenzothiophene, fluorene, and carbazole derivatives was written by Natori, Shinsaku;Ito, Masao;Nakagome, Takenari. And the article was included in Pharmaceutical Bulletin in 1957.Category: benzothiophene This article mentions the following:
Since isosteric compounds often show similar biol. effects, the preceding study was extended to derivatives of compounds having S, SO, SO2, CH2, CO, or NH in place of the O of dibenzofuran. About 40 such compounds were synthesized by familiar methods. Five less well-known syntheses are described. The 2-Br derivative of dibenzothiophene 5-dioxide (I) (3.5 g.) heated 7 hrs. at 200° in an autoclave with 0.2 g. powd. Cu and 70 cc. concentrated NH4OH yielded on cooling 1.8 g. 2-H2N derivative of I, m. 269-70° (BuOH), previously prepared (Brown, et al., C.A. 47, 12346i) by the reduction of the 2-O2N derivative of I. Cyclohexanone condensed with m-O2NC6H4NHNH2 and the product cyclized in the presence of HCl gave a mixture of 5- and 7-O2N derivatives of 1,2,3,4-tetrahydrocarbazole (II), and chromatography separated the 5-O2N derivative, m. 153° (hot C6H6 with rapid cooling) or 116° (hot C6H6 with gradual cooling), dimorphic forms. The 2-O2N derivative of II dehydrogenated with chloranil and the product purified by chromatography in C6H6 over Al2O3 gave the 2-O2N derivative of carbazole (III), m. 174-5° (C6H6), and this catalytically reduced (Pd-C) in EtOH gave the 2-H2N derivative of III, m. 226-38° (decomposition); trinitrobenzene complex, m. 186-8° (EtOH). The 4-O2N derivative of III reduced by Sn and HCl gave the HCl salt of the 4-H2N derivative of III, m. above 300°; free base, m. 230-50° (decomposition); trinitrobenzene complex, m. 216-20° (EtOH). Other compounds prepared and tested were: dibenzothiophene, its 2-Br, 2-H2N, 2-AcNH, 2,8-Br2, 2,8-(H2N)2, 2,8-(AcNH)2, 3-O2N, 3-H2N, 3-AcNH, and 3,7-(O2N)2 derivatives; dibenzothiophene 5-oxide, its 3-O2N, 3-H2N, 3,7-(O2N)2 derivatives; I, its 2-Br, 2-AcNH, 3-O2N, 3-H2N, 3-AcNH, 2,8-Br2, 2,8-(H2N)2, and 2,8-(AcNH)2 derivatives; fluorene, its 2-O2N, and 2-H2N derivatives; fluorenone, its 2-O2N, and 2-H2N derivatives; II, its 7-O2N, 5-H2N, and 7-H2N derivatives; and III, its 4-O2N, and 9-Ac derivatives The antibacterial activities of these 40 compounds were tested and recorded as above, and compared with those of the corresponding dibenzofuran derivatives In the experiment, the researchers used many compounds, for example, Dibenzo[b,d]thiophen-3-amine (cas: 25288-76-0Category: benzothiophene).
Dibenzo[b,d]thiophen-3-amine (cas: 25288-76-0) belongs to benzothiophene derivatives. Functionalized benzothiophenes are important constructs found in molecules with wide ranging biological activity and in organic materials. The different substitution patterns in these heterocycles offer new opportunities for drug discovery and other applications in materials science.Category: benzothiophene
Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem