Synthesis of Some New Bisindole Derivatives and Their Biological Activity

Amal S Yanni

doi:10.4236/ijoc.2016.64019

Abstract

Pyrrolidines are well known for their versatile pharmacological activities such as antimicrobial [1] [2] [3] [4], antitumor [5], anti HIV [6], anticonvulsant [7] [8], human melanocortin-4 receptor agonists [9], etc. Moreover, indole nucleus is an important element of many natural and synthetic molecules that covers some of the relevant and recent achievement in the biological, chemical and pharmaceutical activity of important indole derivatives [10]. In view of these observations, the intention is directed to synthesize some new bisindole derivatives of expected biological interest.

Highlights

Substituted 1,4-diaza-1,3-butadienes with 2 equivalents of 1,4-naphthoquinone in presence of ethanol or benzene produce corresponding substituted bisindoletetrones via criss-cross cycloaddition reaction
Pyrrolidines are well known for their versatile pharmacological activities such as antimicrobial [1] [2] [3] [4], antitumor [5], anti HIV [6], anticonvulsant [7] [8], human melanocortin-4 receptor agonists [9], etc
IR spectra were recorded (KBr) with a Perkin- Elmer 1430 spectrophotometer. 1H NMR spectra were obtained on Varian EM 399.65 MHz equipment

Summary

General

6,13-Diphenyl-6,6a,13,13a-Tetrahydro-(5aH,5bH,12aH, 12bH)-Bisbenzo[f]Benzo-[5,6]Indolo[3,2-b]Indole-5,7,12,14-Tetrone (3a). Adduct (3b), R = -C6H4-p-CH3, is obtained from 1,4-di-p-tolyl-1,4-diaza-1,3-butadiene (1b) and (2) in 40% yield, m.p. 188 ̊C - 190 ̊C. 6,13-Di-p-Methoxyphenyl-6,6a,13,13a-Tetrahydro-(5aH,5bH, 12aH,12bH)-Bisbenzo-[f]Benzo[5,6]Indolo[3,2-b]Indole-5,7,12,14Tetrone (3c). Adduct (3c), R= -C6H4-p-OCH3, is obtained from 1,4-di-p-methoxyphenyl-1,4-diaza1,3-butadiene (1c) and (2) in 42% yield, m.p. 140 ̊C. 6,13-Di-p-Hydroxyphenyl-6,6a,13,13a-Tetrahydro-(5aH,5bH, 12aH,12bH)-Bisbenzo-[f]Benzo[5,6]Indolo[3,2-b]Indole-5,7,12,14Tetrone (3d). Adduct (3d), R= -C6H4-p-OH, is obtained from 1,4-di-p-hydroxyphenyl-1,4-diaza-1,3butadiene (1d) and (2) in 45% yield, m.p. 240 ̊C. 6,13-Di-p-Chlorophenyl-6,6a,13,13a-Tetrahydro-(5aH,5bH, 12aH,12bH)-Bisbenzo-[f]Benzo[5,6]Indolo[3,2-b]Indole-5,7,12,14Tetrone (3e). Adduct (3e), R= -C6H4-p-Cl, is obtained from 1,4-di-p-chlorophenyl-1,4-diaza-1,3butadiene (1e) and (2) in 50% yield, m.p. 205 ̊C. 6,13-Di-α-Naphthyl-6,6a,13,13a-Tetrahydro-(5aH,5bH,12aH, 12bH)Bisbenzo-[f]Benzo[5,6]Indolo[3,2-b]Indole-5,7,12,14-Tetrone (3f). Adduct (3f), R= -C10H7, is obtained from 1,4-di-α-naphthyl-1,4-diaza-1,3-butadiene (1f) and (2) in 38% yield, m.p. 215 ̊C. MS m/z (%): [M+-2C10H7-C2H2-2H] 342 (0.1), common fragment ion [M+ - 2 C10H7 - 2 O] 337.9 (20.9)

Antimicrobial Activity*

Results and Discussion

Conclusion