Synthesis and in vitro anti-HIV-1 evaluation of some N-arylsulfonyl-3-formylindoles

Abstract

As our ongoing work on research of anti-HIV-1 inhibitors, fifteen N-arylsulfonyl-3-formylindoles (3ao) were designed and prepared through two step synthetic route. Firstly, 3-formylindoles (2a-c) were synthesized via the Vilsmeier-Haack reaction. Subsequently, treatment of 2a-c with the appropriate arylsulfonyl chlorides led to the corresponding target compounds in excellent yields. All analogues were also preliminary evaluated in vitro for their inhibitory activity against HIV-1 replication. Among of all the reported analogues, three compounds 3c, 3g and 3i displayed significant anti-HIV-1 activity, with EC 50 values of 9.57, 11.04 and 5.02 μM, and TI values of 31. 89, 13.79 and 81.69, respectively. N-mnitrophenylsulfonyl-3-formylindole (3c) and N-m-nitrophenylsulfonyl-6-methyl-3-formylindole (3i) especially exhibited the best promising anti-HIV-1 activity. In addition, it demonstrated that insertion of a methyl group at the C-6 position of the indolyl ring and a nitro group at the meta position of the arylsulfonyl ring, as in compound 3i, resulted in both low cytotoxicity (CC 50 = 410.41 μM) and good antiviral activity.

Anticancer agents incorporating the N‐acylhydrazone scaffold: Progress from 2017 to present

“…[ 13–19 ] Several studies on the chemistry and bioactivity of N ‐acylhydrazone lead scaffold have been published recently. This topic has gained significance over time for the development of novel, therapeutically effective bioactive N ‐acylhydrazone candidates as anticancer, [ 20–23 ] anti‐inflammatory, [ 24–31 ] anti‐Alzheimer, [ 32–35 ] antimicrobial agents, [ 36–40 ] and more. N ‐Acylhydrazones continue to be a prominent topic in therapeutic research, especially when it comes to the treatment of cancer.…”

Synthesis of Novel Indole Schiff Base Compounds and Their Antifungal Activities

“…Indole is an important nitrogen-containing heterocyclic compound. Indole and indole derivatives have a broad spectrum of biological activities such as antifungal [ 20 , 21 , 22 , 23 , 24 , 25 , 26 ], antibacterial [ 27 , 28 , 29 ], antimycobacterial [ 30 ], antitubercular [ 31 , 32 , 33 ], antioxidant [ 34 ], antimalarial [ 35 , 36 , 37 ], antiviral [ 38 , 39 , 40 , 41 ], anti-leishmanial [ 42 , 43 ], anti-inflammatory [ 44 ], and anti-tumor [ 45 , 46 , 47 ] activities. The design and synthesis of new indole derivatives with excellent biological activity is one of the emerging fields in pharmaceutical chemistry.…”