Synthesis, molecular docking, antimycobacterial and antimicrobial evaluation of new pyrrolo[3,2- c ]pyridine Mannich bases

Jose, Gilish; Kumara, T.H. Suresha; Sowmya, H.B.V.; Sriram, Dharmarajan; Row, Tayur N. Guru; Hosamani, Amar A.; More, Sunil S.; Janardhan, Bhavya; Harish, B. S.; Telkar, Sandeep; Ravikumar, Yalegara Siddappa

doi:10.1016/j.ejmech.2017.03.015

Cited by 27 publications

(13 citation statements)

References 43 publications

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“…[28,29] 4.1. methoxybenzaldehyde (0.01 mol), were refluxed in glacial acetic acid for 7-9 h. The precipitate was filtered and crystallized from acetic acid. [26,27] Ethyl 106-107°C, as reported. [30] 4.1.5 | Synthesis of ethyl 4-[(4-oxothiazolidin-2ylidene)amino]benzoate (5) To a solution of ethyl 4-(2-chloroacetamido)benzoate (4) (0.01 mol) in ethanol (30 ml), ammonium thiocyanate (0.015 mol) was added.…”

Section: Adme and Drug-likeness Predictionmentioning

confidence: 73%

“…Equimolar amounts of ethyl 4‐aminobenzaote ( 1 ), 2‐(benzo[ d ]thiazol‐2‐yl)acetonitrile ( 2 ), and appropriate aldehydes, namely, furaldehyde, benzaldehyde, 4‐chloro benzaldehyde, 4‐fluoro benzaldehyde, and 4‐methoxybenzaldehyde (0.01 mol), were refluxed in glacial acetic acid for 7–9 h. The precipitate was filtered and crystallized from acetic acid. [ 26,27 ]…”

Section: Methodsmentioning

confidence: 99%

“…In Scheme 1, the arylidene derivatives 3a-e were synthesized via refluxing benzocaine 1 with benzothiazole acetonitrile 2 and appropriate aromatic aldehydes in glacial acetic acid. [26,27] The synthon 2 was prepared via the cyclization reaction of O-aminothiophenol and malononitrile according to the reported procedure. [28,29] On the other hand, chloroacetamide benzoate derivative 4 was obtained in a good yield from benzocaine 1 by treatment with chloroacetyl chloride using acetic acid as a solvent stirred in a warm water bath for 15 min according to the reported procedure.…”

Section: Chemistrymentioning

confidence: 99%

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Antibacterial and anticancer profiling of new benzocaine derivatives: Design, synthesis, and molecular mechanism of action

Elzahabi

Nossier

Mousa

et al. 2022

Archiv der Pharmazie

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The need for new chemotherapeutics to overcome development of resistance merits research to discover new agents. Benzocaine derivatives are essential compounds in medicinal chemistry due to their various biological activities including antibacterial and anticancer activities. Therefore, this study focuses on the synthesis of new benzocaine derivatives 3a–e, 6, 7a and 7b, 8, 10–14, and 16a–d and their in vitro evaluation as antibacterial agents against gram +ve and –ve strains and as anticancer agents against HepG‐2, HCT‐116, and MCF‐7 human cancer cell lines. The obtained results demonstrated that thiazolidines 6 and 7b showed higher antibacterial and anticancer activity in comparison with the reference drugs. In addition, 6 and 7b showed high potency as inhibitors toward their biological targets, that is DNA gyrase and human topoisomerase IIα, as compared to the reference standard drugs novobiocin and etoposide, respectively. Molecular docking demonstrated that both compounds could identify the active site of their target enzymes and develop effective binding interactions. Absorption, distribution, metabolism and elimination (ADME) and drug‐likeness predictions of both compounds showed that they both have good ADME profiles and no structural alerts that might cause toxicity. Based on this, 6 and 7b could serve as lead compounds for the design of more potent antibacterial and anticancer agents.

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Section: Adme and Drug-likeness Predictionmentioning

confidence: 73%

Section: Methodsmentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

See 1 more Smart Citation

Antibacterial and anticancer profiling of new benzocaine derivatives: Design, synthesis, and molecular mechanism of action

Elzahabi

Nossier

Mousa

et al. 2022

Archiv der Pharmazie

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“…Mannich bases result from a three-component condensation between a substrate with acidic hydrogen, an aldehyde and an amine. Heterocycles Mannich bases are remarkable compounds with various medicinal properties such as: antimicrobial [1][2][3][4][5][6][7][8], anticancer [9,15], antiviral [9,10], analgesic [11][12][13], anticonvulsant [2,10] anti-inflammatory [11][12][13][14], anti-HIV [2,10], antimalarial [15], anti-Alzheimer [16,17], anthelmintic [15], antioxidant [16,17] and so forth. Recent studies show Mannich bases as multifunctional agents against Parkinson disease, with good in vitro anti-inflammatory and neuroprotective effects [18].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, density functional theory study and in vitro antimicrobial evaluation of new benzimidazole Mannich bases

et al. 2020

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The tri-component synthesis of novel chiral benzimidazole Mannich bases, by reaction between benzimidazole, aqueous 30% formaldehyde and an amine, the biological evaluation and DFT studies of the new compounds are reported here. The 1 H-NMR, 13 C-NMR, FTIR spectra and elemental analysis confirm the structures of the new compounds. All synthesized compounds were screened by qualitative and quantitative methods for their in vitro antibacterial activity against 4 bacterial strains. DFT studies were accomplished using GAMESS 2012 software and HOMO-LUMO analysis allowed the calculation of electronic and structural parameters of the chiral Mannich bases. The geometry of 1-methylpiperazine, the cumulated Mullikan atomic charges of the two heteroatoms and of the methyl, and the value of the global electrophilicity index (ω = 0.0527) of the M-1 molecule is correlated with its good antimicrobial activity. It was found that the presence of saturated heterocycles from the amine molecule, 1-methyl piperazine and morpholine, respectively, contributes to an increased biological activity, compared to aromatic amino analogs, diphenylamino-, 4-nitroamino-and 4-aminobenzoic acid. The planarity of the molecules, specific bond lengths and localization of HOMO-LUMO orbitals is responsible for the best biological activities of the compounds.

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“…Mannich bases received enormous appreciation for their immense realm of applications and many studies have focussed on structural modifications of the Mannich bases and on the vast variety of their biological activities [9,10]. A number of synthetic modifications, such as heterocyclic infused [11,12], thiophene based [13], aurone based mannich bases [14], lawsone based mannich bases [15], berberine based mannich bases [16],or other substitutions [17][18][19][20], have also been reported to affect the biological activities including anticancer activities [21,22] of these bases.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of Novel 5-Oxo-1-Phenylpyrrolidine-3-Carboxylic Acid Analogs

et al. 2018

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A number of 5-oxo-1-phenyl-4-(substituted methyl) pyrrolidine-3-carboxylic acid derivatives bearing pyrrolidine ring and methylamino residues in their structure were synthesized as potential antibacterial drugs. The chemical structures of all the compounds were established by their UV-Vis absorption spectroscopy, IR, H,C NMR and mass spectroscopy. The in vitro antibacterial screening of all novel compounds was done against gram-positive Staphylococcus aureus, Bacillus subtilis and gram-negative Pseudomonas aeruginosa. The results revealed that compounds 5d, e, f and g showed moderate to good activity against the tested microbes.

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Synthesis, molecular docking, antimycobacterial and antimicrobial evaluation of new pyrrolo[3,2- c ]pyridine Mannich bases

Cited by 27 publications

References 43 publications

Antibacterial and anticancer profiling of new benzocaine derivatives: Design, synthesis, and molecular mechanism of action

Antibacterial and anticancer profiling of new benzocaine derivatives: Design, synthesis, and molecular mechanism of action

Synthesis, density functional theory study and in vitro antimicrobial evaluation of new benzimidazole Mannich bases

Synthesis and Biological Evaluation of Novel 5-Oxo-1-Phenylpyrrolidine-3-Carboxylic Acid Analogs

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