Synthesis of some new 2-amino-6-thiocyanato benzothiazole derivatives bearing 2,4-thiazolidinediones and screening of their in vitro antimicrobial, antitubercular and antiviral activities

Shaikh, Faiyazalam M.; Patel, Navin B.; Sanna, Giuseppina; Busonera, Bernardetta; Colla, Paolo La; Rajani, Dhanji P.

doi:10.1007/s00044-015-1358-0

Cited by 45 publications

(31 citation statements)

References 26 publications

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“…The synthesis of TZD derivatives (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20) were accomplished using the synthetic route depicted in Scheme 1. At first, 2-chloroacetic acid was treated with thiourea in conc.…”

Section: Chemistrymentioning

confidence: 99%

“…Further, the reaction of (I) with terephthalaldehyde yielded 4-((2,4-dioxothiazolidin-5-ylidene) methyl) benzaldehyde (II). Intermediate-II on further treatment with substituted anilines/amines yielded final 5-((E)-4-((E)-(substituted aryl/alkyl)methyl)benzylidene)thiazolidine-2,4-dione derivatives (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20). The physicochemical characterization and spectral analysis of the synthesized derivatives are given in Table 1.The molecular structures of the synthesized derivatives (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20) were established using elemental analysis and spectral studies [FT-IR (KBr, cm -1 ), 1…”

Section: Chemistrymentioning

confidence: 99%

“…To the solution of compound II (0.01 mol) in methanol (50 mL), different substituted amines (0.01 mol) were added using catalytic amount of acetic acid (glacial) and refluxed for 4-18 h. The reaction mixture was then allowed to cool and finally recrystallized from methanol to give final compounds (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20).…”

Section: Step 3: Synthesis Of Various Title Compounds (1-20)mentioning

confidence: 99%

“…Small heterocyclic rings having sulfur and nitrogen atoms like 4 thiazolidine-2,4-dione (TZD) have been under study for a long time due to their synthetic variety and therapeutic relevance [4]. The TZD moiety is reported to possess extensive biological potential such as antifungal [5], analgesic, anti-inflammatory [6], hypoglycemic [7], antimalarial [8], antiproliferative [9], antitubercular [10], antioxidant [11], antiviral [12], hypolipidemic [13] and antibacterial [14][15][16] etc. The biological potential of TZD moiety is displayed in Fig.…”

Section: Introductionmentioning

confidence: 99%

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Design, synthesis, in silico studies and biological evaluation of 5-((E)-4-((E)-(substituted aryl/alkyl)methyl)benzylidene)thiazolidine-2,4-dione derivatives

Kumar

Deep

Marwaha

2020

Preprint

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Background: Looking at the extensive range of biological potential of thiazolidine-2,4-dione (TZD) moiety, a new series of thiazolidine-2,4-dione analogues was synthesized. Different spectral techniques (1H-NMR, IR, MS etc.) were used to confirm the chemical structures of the synthesized analogues. These synthesized compounds were then screened for their antioxidant and antimicrobial potential.Results and discussion: The antimicrobial screening was carried out against selected strains of fungi and bacteria using serial tube dilution method. The antioxidant potential was assessed using stable 2, 2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging method. Further, the interaction between synthesized thiazolidine-2,4-dione compounds and DNA gyrase was explored using molecular docking studies. Various ADME parameters were also studied to evaluate the drug likeness of the synthesized compounds. Conclusion: In antimicrobial evaluation, the compounds 4, 9, 11, 12, 13, 15 and 16 displayed promising activity against selected strains of microbes. Antioxidant evaluation found compound 6 having IC50 = 9.18 μg/mL to be the most potent compound in the series. The molecular docking study revealed compounds 4 (dock score = -4.73) and 7 (dock score = -4.61) with decent docking score possess good interaction inside the ATP binding pocket and therefore can be used as lead structure for further optimizing into potent antimicrobial molecule.

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Section: Chemistrymentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Section: Step 3: Synthesis Of Various Title Compounds (1-20)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Design, synthesis, in silico studies and biological evaluation of 5-((E)-4-((E)-(substituted aryl/alkyl)methyl)benzylidene)thiazolidine-2,4-dione derivatives

Kumar

Deep

Marwaha

2020

Preprint

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“…They are associated with various biological activities, for example, anticancer activity , because of inhibition of vital enzymes, namely, cytochrome P450 enzyme , EGFR tyrosine kinase , or COX‐2 enzyme . In addition, these derivatives are considered as antimicrobial , anti‐inflammatory , antioxidant , antitubercular , and antimalarial agents. Moreover, incorporation of thiophene nucleus at position 2 of benzothiazole gives rise to compounds possessing potent anticancer and antimicrobial activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Anticancer Evaluation of Some Novel Thiophene, Thieno[3,2‐d]pyrimidine, Thieno[3,2‐b]pyridine, and Thieno[3,2‐e][1,4]oxazepine Derivatives Containing Benzothiazole Moiety

Hassan

Husseiny

2019

Journal of Heterocyclic Chem

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In an attempt to establish novel candidate with promising anticancer activity, two derivatives of (benzo[d]thiazol‐2‐yl)thiophene backbone 1 and 14 were synthesized, and they further reacted with various chemical reagents to afford the corresponding substituted thiophene derivatives 6, 8, 10, 15, 17, and 20, thieno[3,2‐d]pyrimidine derivatives 2–5, 7, 9, 16, 21, 23, and 24, thieno[3,2‐b]pyridine derivatives 11–13, and thieno[3,2‐e][1,4]oxazepine derivative 18. Structures of prepared compounds were affirmed via spectral and elemental data. Among the obtained compounds, seven derivatives 2, 3, 4, 5, 11, 12, and 13 were chosen by National Cancer Institute, USA. Such compounds were screened for their antitumor activity versus 60 cancer cell lines in one‐dose (10 μmol) screening assay. The outcomes showed that all selected compounds exhibited moderate to high anticancer activity towards many cancer cell lines among which compounds 5 and 11 exerted potent antitumor activity against numerous malignant growth cell lines particularly Ovarian Cancer IGROV1.

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Asymmetric Synthesis of 2‐Thiocyanato‐2‐(1‐aminoalkyl)‐substituted 1‐Tetralones and 1‐Indanones with Tetrasubstituted Carbon Stereogenic Centers via Cooperative Cation‐Binding Catalysis

Lei

Kim

et al. 2017

Adv Synth Catal

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In this study, the concept of cooperative cation‐binding catalysis was applied for direct generation of two contiguous trisubstituted and tetrasubstituted stereogenic centers. Using the readily accessible chiral oligoethylene glycol (oligoEG) as a cation‐binding catalyst, asymmetric Mannich reactions of α‐thiocyanato cyclic ketones as Mannich donors were performed with α‐amidosulfones as the bench‐stable imine precursors in the presence of potassium fluoride as the base, affording 2‐thiocyanato‐2‐(1‐aminoalkyl)‐substituted 1‐tetralones and 1‐indanones possessing fully substituted C–SCN centers. The salient features of this process include (i) a transition metal‐free and operationally simple procedure, (ii) direct use of α‐amidosulfones as bench‐stable precursors of sensitive imines, (iii) direct enolization of racemic cyclic α‐thiocyanato ketones and (iv) excellent stereoselectivity with up to 99% ee and >20:1 diastereoselectivity (anti:syn). This protocol is easily scalable and provides a new approach for the syntheses of some biologically relevant products possessing fully substituted C–SCN centers.magnified image

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Synthesis of some new 2-amino-6-thiocyanato benzothiazole derivatives bearing 2,4-thiazolidinediones and screening of their in vitro antimicrobial, antitubercular and antiviral activities

Cited by 45 publications

References 26 publications

Design, synthesis, in silico studies and biological evaluation of 5-((E)-4-((E)-(substituted aryl/alkyl)methyl)benzylidene)thiazolidine-2,4-dione derivatives

Design, synthesis, in silico studies and biological evaluation of 5-((E)-4-((E)-(substituted aryl/alkyl)methyl)benzylidene)thiazolidine-2,4-dione derivatives

Synthesis and Anticancer Evaluation of Some Novel Thiophene, Thieno[3,2‐d]pyrimidine, Thieno[3,2‐b]pyridine, and Thieno[3,2‐e][1,4]oxazepine Derivatives Containing Benzothiazole Moiety

Asymmetric Synthesis of 2‐Thiocyanato‐2‐(1‐aminoalkyl)‐substituted 1‐Tetralones and 1‐Indanones with Tetrasubstituted Carbon Stereogenic Centers via Cooperative Cation‐Binding Catalysis

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