Synthesis and biological evaluation of 2,4,5-trisubstituted thiazoles as antituberculosis agents effective against drug-resistant tuberculosis

Karale, Uttam B.; Krishna, Vagolu Siva; Krishna, E. Vamshi; Choudhari, Amit; Shukla, Manjulika; Gaikwad, Vikas R.; Mahizhaveni, B.; Chopra, Sidharth; Misra, Sunil; Sarkar, Dhiman; Sriram, Dharmarajan; Dusthackeer, V.N. Azger; Rode, Haridas B.

doi:10.1016/j.ejmech.2019.05.082

Cited by 36 publications

(26 citation statements)

References 35 publications

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“…Molecules 2021, 26, x 21 of 74 59g showed aromatic and hydrophobic interaction with amino acid residues of the enzyme as well as van der Waals interactions, while compound 59k formed a hydrogen bond with MET103 except for almost the same aromatic, hydrophobic, and van der Waals interactions. Karale et al [91] synthesized a series of 2,4,5-trisubstituted thiazoles (50) and evaluated their inhibitory potential against M. tuberculosis strain H37Rv using MABA assay. Compounds 60a-h (Figure 23) showed antituberculosis activity with an MIC range of 1.8-40 μg/mL.…”

Section: Antituberculosismentioning

confidence: 99%

“…Finally, compounds with an MIC ≤ 4.2 μg/mL were found to be nontoxic against CHO-KI cells. Cordeiro et al [92] reported the synthesis of 2-amino thiazole Schiff bases (Figure 24) and evaluation of their anti-tuberculosis activity against Mycobacterium tuberculosis Karale et al [91] synthesized a series of 2,4,5-trisubstituted thiazoles (50) and evaluated their inhibitory potential against M. tuberculosis strain H37Rv using MABA assay. Compounds 60a-h (Figure 23) showed antituberculosis activity with an MIC range of 1.8-40 µg/mL.…”

Section: Antituberculosismentioning

confidence: 99%

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Thiazole Ring—A Biologically Active Scaffold

2021

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Background: Thiazole is a good pharmacophore nucleus due to its various pharmaceutical applications. Its derivatives have a wide range of biological activities such as antioxidant, analgesic, and antimicrobial including antibacterial, antifungal, antimalarial, anticancer, antiallergic, antihypertensive, anti-inflammatory, and antipsychotic. Indeed, the thiazole scaffold is contained in more than 18 FDA-approved drugs as well as in numerous experimental drugs. Objective: To summarize recent literature on the biological activities of thiazole ring-containing compounds Methods: A literature survey regarding the topics from the year 2015 up to now was carried out. Older publications were not included, since they were previously analyzed in available peer reviews. Results: Nearly 124 research articles were found, critically analyzed, and arranged regarding the synthesis and biological activities of thiazoles derivatives in the last 5 years.

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Section: Antituberculosismentioning

confidence: 99%

Section: Antituberculosismentioning

confidence: 99%

Thiazole Ring—A Biologically Active Scaffold

2021

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“…Therefore, analogues bearing thiazoles which are the NÀ S containing five membered heterocyclic ring structures coming under the group of azoles are one of the most privileged scaffolds in drug and remains of great importance, because of their potent biological activity against variety of diseases (Figure 1) such as Tiazofurin and Dasatinib (anticancer), Sulfathiazole (antimicrobial), Abafungin (anti-fungal), and Meloxicam (anti-inflammatory). [7] Even more, thiazole or thiazolyl scaffold showed multifunctional therapeutics effect from antimicrobial and antifungal, [8][9][10] to antitubercular, [11] anticancer, [12,13] anticandidal, [14] anti-HIV [15] and antidiabetic [16] agents. Also, pyrazoles, which are fivemembered heterocyclic rings containing two adjacent nitrogen possess a large spectrum of activity have been proved for their antimicrobials [17] and anticancer effect.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Structure‐Activity Relationship and in silico Studies of Novel Pyrazolothiazole and Thiazolopyridine Derivatives as Prospective Antimicrobial and Anticancer Agents

et al. 2021

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In our attempt to develop potential new drug candidates with promising dual antimicrobial and anticancer activities, a series of pyrazolothiazole and thiazolopyridine analogues has been synthesized. All compounds were evaluated for their antimicrobial potential towards pathogenic strains and cytotoxicity properties against hepatic cancer cell line HepG-2 and breast cancer cell line MCF-7. 9 c showed excellent antimicrobial activity against the tested strains, with MIC values about 27.5 μM (S. epidermidis), 6.8 (B. subtilis) and 3.4 μM (S. pneumoniae and K. pneumoniae) fold higher than the reference drug, whilst 9 a, 9 b and 5 a exhibited also potent activity against selected strains. Moreover, compounds 9 c (IC50 = 10.89 μM and 15.60 μM) and 9 a (IC50 = 22.24 μM and 28.47 μM) showed promising anticancer activity for HepG2 and MCF-7 cell lines, respectively, when compared to the known anticancer drugs, 5-Fluorouracil (IC50 = 26.75 μM and IC50 = 32.75 μM). The data from structure-activity relationships analysis revealed the potency of pyrazolothiazole than thiazolopyridine derivatives in generating potential activity. Further, molecular docking studies performed on the more active antimicrobial and cytotoxic compound, 9 c to get insights for binding modes to the target enzymes (PDB ID: 1JIJ) for antimicrobial, and (PDB ID: 1DI8) and (PDB ID: 3TWJ) for anticancer revealed that they interacted with the same key amino acids with TyrRS for S. aureus, CDK2 and ROCK1, respectively.

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“…This is in continuation of our efforts to develop new heterocyclic antibacterial leads. [18][19][20][21][22][23] 2 | RESULTS AND DISCUSSION…”

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Synthesis of novel 4,5‐dihydropyrrolo[1,2‐a]quinoxalines, pyrrolo[1,2‐a]quinoxalin]‐2‐ones and their antituberculosis and anticancer activity

Makane

Krishna

Karale

et al. 2020

Archiv der Pharmazie

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A facile strategy was developed for the synthesis of biologically important 4,5dihydropyrrolo[1,2-a]quinoxalines and pyrrolo[1,2-a]quinoxalin]-2-ones by treating 2-(1H-pyrrol-1-yl)anilines with imidazo[1,2-a]pyridine-3-carbaldehyde or isatin, using amidosulfonic acid (NH 3 SO 3) as a solid catalyst in water at room temperature. The protocol has been extended to electrophile ninhydrin. The catalyst could be recycled for six times without the loss of activity. The compounds were evaluated for their antituberculosis, antibacterial, and anticancer activities. It is worth noting that compounds 3d and 3e demonstrated a minimum inhibitory concentration value of 6.25 µM against Mycobacterium tuberculosis H37Rv, whereas compounds 3d, 3g, 5d, 5e, and 5i showed a remarkable inhibition of A549, DU145, HeLa, HepG2, MCF-7, and B16-F10 cell lines, respectively. Staphylococcus aureus was inhibited by compounds 5b, 5e, 5d, 5g, and 5l at 32 µg/ml. K E Y W O R D S 4,5-dihydropyrrolo[1,2-a]quinoxalines, antituberculosis agents, pyrrolo[1,2-a]quinoxalin-2-ones, reusable catalyst 1 | INTRODUCTION Quinoxalines are nitrogen-containing heterocyclic compounds [1] exhibiting various biological activities, [2] acting as glucagon receptor antagonist, [3] inhibitors of human protein kinase CK2, [4] 5-HT 3 receptor agonist, [5] and gamma-aminobutyric acid receptor agonist. [6] Among these quinoxalines (Figure 1), 4,5-dihydropyrrolo[1,2-a]quinoxaline (1) is a key pharmacologically privileged scaffold exhibiting various activities including polycystic kidney disease inhibition. [7] The pyrrolo[1,2-a]quinoxaline derivative 2 showed an antipsychotic activity, [8] whereas 3 was found to be an adenosine A3 receptor modulator. [9] The pyrrolo[1,2-a]quinoxaline 4 has shown anti-HIV potential, [10] whereas 5 has been reported for its antiproliferative activity. [11] There are few reports on the synthesis of 4,5-dihydropyrrolo[1,2-a] quinoxalines and their spiro derivatives. [12] Preetham and Nath [13] reported the synthesis of pyrrolo-[1,2-a]quinoxalines and spiro derivatives using 2-(1H-pyrrol-1-yl)aniline with aldehyde or isatin or ketone in the presence of p-dodecylbenzenesulfonic acid catalyst in ethanol. Verma et al. [14] used 10 mol% AlCl 3 in tetrahydrofuran for the same transformation. In contrast, Zhou et al. [15] synthesized 12b-methyl-1,12bdihydrodipyrrolo[1,2-a:2′,1′-c]quinoxalin-3(2H)-one from 2-(1H-pyrrol-1yl)aniline and 4-pentynoic acid in the presence of Au(I) catalyst in water at 100°C. 14 Water Amidosulfonic acid 3 98 15 Water Amidosulfonic acid 4 98 Note: Reagents and conditions: 1a (0.088 mmol), 2a (0.088 mmol, 25 mg) in 2.0 ml of solvent at room temperature. Isolated yields (without column chromatography).

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Synthesis and biological evaluation of 2,4,5-trisubstituted thiazoles as antituberculosis agents effective against drug-resistant tuberculosis

Cited by 36 publications

References 35 publications

Thiazole Ring—A Biologically Active Scaffold

Thiazole Ring—A Biologically Active Scaffold

Synthesis, Structure‐Activity Relationship and in silico Studies of Novel Pyrazolothiazole and Thiazolopyridine Derivatives as Prospective Antimicrobial and Anticancer Agents

Synthesis of novel 4,5‐dihydropyrrolo[1,2‐a]quinoxalines, pyrrolo[1,2‐a]quinoxalin]‐2‐ones and their antituberculosis and anticancer activity

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