Design, synthesis of novel N prenylated indole-3-carbazones and evaluation of in vitro cytotoxicity and 5-LOX inhibition activities

Abstract

A series of novel N-1 and C-3 substituted indole derivatives (5a-f) were designed, synthesized and evaluated for their cytotoxic properties, viz Brine Shrimp Lethality Bioassay (BSLB) besides 5-Lipoxygenase (5-LOX) inhibitory activities through in vitro assays. Structure Activity Relation (SAR) studies showed that compound 5d with an LC 50 of 6.49 lM and 5c with an IC 50 of 33.69 lM were found to be interesting for cytotoxicity and 5-LOX inhibitory activity respectively. ª 2015 Production and hosting by Elsevier B.V. on behalf of King Saud University. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).

Indole-3-carbaldehyde Semicarbazone Derivatives: Synthesis, Characterization, and Antibacterial Activities

“…e IR spectra of the compounds 1-4 showed absorption bands in the range of 3200-3450 cm −1 which are assigned to the N-H groups of the indole ring and terminal amine group (−NH 2 ) [27,32]. e absorption bands corresponding to the carbonyl group (C�O) appeared at 1639-1681 cm −1 [27,32,33]. is observed band indicates the presence of the keto tautomer in the solid state [34].…”

Synthesis, characterization and cytotoxic investigations of novel bis(indole) analogues besides antimicrobial study

“…The precipitate was filtered off and washed thrice with 100 mL water, yielding 5-substituted 1H-indole-3-carbaldehyde (5a,b). (5a): (James and Snyder, 1959;Choppara et al, 2015) Yield: 92%., Brownish yellow solid., ., 1 H NMR (DMSO-d 6 , 400 MHz): d 7.14 (t, J = 7.2 Hz, 1H), …”

“…General procedure for preparation of indole-3-carboxylic acid hydrazides (3a-c): (Rapolu et al, 2013) 4.4. General procedure for the synthesis of 5-substituted 1H-indole-3-carbaldehyde (5a,b): (James and Snyder, 1959;Choppara et al, 2015) To a solution of substituted indoles (4a,b) (42.6 mmol) in dry DMF (187.4 mmol) in an ice-salt bath, POCl3 (47.1 mmol) is subsequently added with stirring over a period of 30 min. After completion of addition, raise the temperature to 40°C and stir the syrup for 1.5 h at that temperature.…”

“…On the other hand, N-1 and C-3-substituted indole derivatives have been found to play an important role in many biologically active compounds especially with antiinflammatory (Hall et al, 2008;Singh et al, 2008), anticancer (Singh et al, 2008;Madadi et al, 2014), anti-nociceptive (Adam et al, 2010) and antipsychotic (Madadi et al, 2013) activities. Marine indole alkaloids have emerged as an important structural class exhibiting antiviral, antimicrobial and antitumor activity (Dembitsky et al, 2005;Bao et al, 2005;Oh et al, 2005Oh et al, , 2006. Among these biologically active scaffolds, bis(indole) alkaloids with a broad spectrum of biological activities are being discovered from marine invertebrates such as sponges, bryozoans, coelenterates and tunicates (Yang and Cordell, 1997;Tsuda et al, 2005;Shin et al, 1999;Ryan and Drennan, 2009;Diana et al, 2010).…”

A brief review of the biological potential of indole derivatives

“…Whereas in vivo anti-inflammatory activity was good for the compound having SO 2 Me moiety and compounds (3-ethyl-5-(methylsulfonyl)-2-phenyl-1H-indol-1-yl)(4-fluorophenyl)methanone (31) and (4-chlorophenyl)(3ethyl-5-(methylsulfonyl)-2-phenyl-1H-indol-1-yl)methanone (32) were more potent than indomethacin. The presence of a carbonyl moiety as a spacer instead of methylene resulted in an increase in the anti-inflammatory activity [19] 3-Methyl-2-phenyl-1-substituted-indole derivatives were synthesized and investigated for anti-inflammatory (in vitro and in vivo) and analgesic activities by Abdellatif et al Derivatives (3-methyl-5-(methylsulfonyl)-2phenyl-1H-indol-1-yl)(phenyl)methanone (33), (4-chlorophenyl)(3-methyl-5-(methylsulfonyl)-2-phenyl-1Hindol-1-yl)methanone (34), and 1-benzyl-3-methyl-5-(methylsulfonyl)-2-phenyl-1H-indole (35) showed the highest anti-inflammatory (in vitro and in vivo) and analgesic activities. The results of molecular docking studies were in agreement with that obtained from the in vitro COX inhibition assays [20].…”