Synthesis, characterization, and SAR studies of new (1H-indol-3-yl)alkyl-3-(1H-indol-3-yl)propanamide derivatives as possible antimicrobial and antitubercular agents

Karuvalam, Ranjith P.; Pakkath, Rajeesh; Haridas, Karickal R.; Rathnasamy, Rishikesan; Kumari, N. Suchetha

doi:10.1007/s00044-012-0451-x

Cited by 7 publications

(4 citation statements)

References 20 publications

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“…Among the acyclic sn-1 substituents, 3-isobutyl-5-methylhexanoyl chloride ( 32 ) was prepared according to previous methods . Knoevenagel condensation of methylindole carbaldehyde ( 11 ) with malonate provided the α,β-unsaturated carboxylic acid ( 35 ) . Commercial sources of benzo[ b ]thiophene-3-carbaldehyde ( 19 ), picolinaldehyde ( 20 ), p -phenyl derivatives ( 21 - 26 ), linear, cyclo- or branched- alkyl derivatives ( 27 – 31 ), and aryl acrylic acids ( 33 – 34 ) were directly used for R 1 and R 2 substituents.…”

Section: Resultsmentioning

confidence: 99%

α-Arylidene Diacylglycerol-Lactones (DAG-Lactones) as Selective Ras Guanine-Releasing Protein 3 (RasGRP3) Ligands

et al. 2018

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Diacylglycerol-lactones have proven to be a powerful template for the design of potent ligands targeting C1 domains, the recognition motif for the cellular second messenger diacylglycerol. A major objective has been to better understand the structure activity relations distinguishing the seven families of signaling proteins that contain such domains, of which the protein kinase C (PKC) and RasGRP families are of particular interest. Here, we synthesize a series of aryl- and alkyl-substituted diacylglycerol-lactones and probe their relative selectivities for RasGRP3 versus PKC. Compound 96 showed 73-fold selectivity relative to PKCα and 45-fold selectivity relative to PKCε for in vitro binding activity. Likewise, in intact cells, compound 96 induced Ras activation, a downstream response to RasGRP stimulation, with 8-29 fold selectivity relative to PKCδ S299 phosphorylation, a measure of PKCδ stimulation.

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Section: Resultsmentioning

confidence: 99%

α-Arylidene Diacylglycerol-Lactones (DAG-Lactones) as Selective Ras Guanine-Releasing Protein 3 (RasGRP3) Ligands

et al. 2018

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“…Among heterocyclic systems, the benzimidazole core is found in many biologically relevant molecules which requires the functionalization of this framework using palladiummediated cross-coupling reactions. [9][10][11][12][13][14][15][16] As a part of our research efforts towards developing protocols that incorporate structural diversity into a heteroaromatic system, [17][18][19][20][21][22][23][24][25][26] we envisioned a Suzuki-Miyaura crosscoupling methodology to access 2-aryl/heteroaryl-substituted benzimidazoles. In recent years, the use of microwave energy in organic synthesis has gained much popularity in both industrial and academic research.…”

Section: Introductionmentioning

confidence: 99%

Suzuki-Miyaura coupling under microwave enhanced conditions: synthesis of 2-(hetero)aryl benzimidazoles

Karuvalam¹,

Haridas²,

Sajith³

et al. 2020

Arkivoc

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An expedient, palladium-mediated cross-coupling approach to functionalize the benzimidazole-based core under microwave-assisted conditions has been developed and is described. This protocol, which incorporates appendage diversity on this potential scaffold, is found to be compatible with a wide range of electronicallyand sterically-divergent (hetero)aryl boronic acids. The use of the PdCl 2 /(SPhos) catalytic system allows the formation of a stable and highly active LPd(0) species which was found to be critical for the successful synthesis of these novel, pharmacologically-relevant molecules.

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“…[1] Many synthesized derivatives have potent activity against fungi,viruses and Leishmania parasites as well as Gram-positive and Gramnegativebacteria and mycobacterial species. [2][3][4] Recently,much attention has been paid to indole core derivatives due to theirdiverse biological activities, for instance, the inhibition of bacteria, viruses, leishmania parasites and cancerous cells. [5][6] Indolemoiety has been employed in the designing of new heterocyclic compounds with diversebiological and pharmacological properties like antimicrobial, antitubercular, antimalarial,antitubulin, α-glucosidase inhibitors, antioxidant and fluorescent metal probes to sense molecularrecognitions.…”

Section: Introductionmentioning

confidence: 99%

Assessment of Antimicrobial, Anti-Inflammatory Activity and Docking Study of Novel 2-Arylimino-5-Indole-2-Yl-Methylidene-1, 3-Thiazolidine-4-one Derivatives

Chopra¹,

Kaur²,

Kaur³

2018

IJTSRD

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A novel series of 2-(arylimino)-5-(indole-2-ylmethylidene)-1,3-thiazolidine-4-onederivatives were synthesized and screened for their anti-inflammatory and analgesic potential. The structures of newly synthesized compounds were confirmed by their analytical and spectroscopic data using IR and 1H-NMR. The novel compounds were evaluated for their anti-inflammatory potential using carrageenan induced paw edema model and analgesic activity using acetic acid induced abdominal writhing test. Three compounds 4g,4m and 4o alleviated inflammation more than the standard drug Diclofenac Sodium. The synthesized compounds also showed significant analgesic activity. Insilicomoleculardocking studies of the synthesized compounds were done on crystal structure of Cyclooxygenase-2using Glide version 5.0 following the standard procedure recommended by Schrodinger to study their observed activity, which revealed a significant correlation between the binding score and biological activity for these compounds. Maximum Glide score was obtained for compound 4o having a value of-7.42. This compound showed one interaction with the enzyme.

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Synthesis, characterization, and SAR studies of new (1H-indol-3-yl)alkyl-3-(1H-indol-3-yl)propanamide derivatives as possible antimicrobial and antitubercular agents

Cited by 7 publications

References 20 publications

α-Arylidene Diacylglycerol-Lactones (DAG-Lactones) as Selective Ras Guanine-Releasing Protein 3 (RasGRP3) Ligands

α-Arylidene Diacylglycerol-Lactones (DAG-Lactones) as Selective Ras Guanine-Releasing Protein 3 (RasGRP3) Ligands

Suzuki-Miyaura coupling under microwave enhanced conditions: synthesis of 2-(hetero)aryl benzimidazoles

Assessment of Antimicrobial, Anti-Inflammatory Activity and Docking Study of Novel 2-Arylimino-5-Indole-2-Yl-Methylidene-1, 3-Thiazolidine-4-one Derivatives

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