(E)-2-(2-Allylidenehydrazinyl)thiazole derivatives: Design,
green synthesis, in silico and in vitro antimycobacterial and
radical scavenging studies

J 2020

(E)-2-(2-Allylidenehydrazinyl)thiazole derivatives: Design, green synthesis, in silico and in vitro antimycobacterial and radical scavenging studies

HUBLIKAR, M., V. KADU, Jitender KUMAR, D. RAUT, S. SHIRAME et. al.

Basic information

Original name

(E)-2-(2-Allylidenehydrazinyl)thiazole derivatives: Design, green synthesis, in silico and in vitro antimycobacterial and radical scavenging studies

Authors

HUBLIKAR, M., V. KADU, Jitender KUMAR (356 India, guarantor, belonging to the institution), D. RAUT, S. SHIRAME, P. MAKAM and R. BHOSALE

Edition

Archiv der Pharmazie. Weinheim, Verlag Chemie, 2020, 0365-6233

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

30104 Pharmacology and pharmacy

Country of publisher

Germany

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 3.751

RIV identification code

RIV/00216224:14740/20:00118399

Organization unit

Central European Institute of Technology

DOI

http://dx.doi.org/10.1002/ardp.202000003

UT WoS

000530383800001

Keywords in English

(E)-2-(2-allylidenehydrazinyl)thiazoles; anti-inflammatory; antituberculosis; radical scavenger; beta-ketoacyl-ACP synthase

Abstract

V originále

By understanding the rampant infections of Mycobacterium tuberculosis (Mtb) and inflammations caused due to the generation of radical species during the Mtb infection, a series of (E)-2-(2-allylidenehydrazinyl)thiazole derivatives, with dual-action properties, was designed. The molecules were designed with a considerable variation in LogP, one of the critical parameters in physicochemical properties, and analyzed for their drug-likeness. For the synthesis, a simple, green, and multicomponent one-pot synthesis method was developed. The in vitro inhibition potentials were evaluated against Mtb H(37)Rv by the microplate Alamar Blue assay. The results reveal that compound 6 was potent, with a MIC value of 6.5 mu g/ml, and showed better interactions with the KasA protein with binding free energy (Delta G) of -9.4 kcal/mol. Also, the radical scavenging properties were studied to establish the dual-action properties of the molecules. Compound 9 exhibited promising antioxidant and nitric oxide radical scavenging activities, with 81.7% and 81.0%, respectively, at 1,000-mu g/ml concentration.

Citovat

HUBLIKAR, M., V. KADU, Jitender KUMAR, D. RAUT, S. SHIRAME, P. MAKAM and R. BHOSALE. (E)-2-(2-Allylidenehydrazinyl)thiazole derivatives: Design, green synthesis, in silico and in vitro antimycobacterial and radical scavenging studies. Archiv der Pharmazie. Weinheim: Verlag Chemie, 2020, vol. 353, No 7, p. 2000003-2000014. ISSN 0365-6233. Available from: https://dx.doi.org/10.1002/ardp.202000003.

@article{1752816,
   author = {Hublikar, M. and Kadu, V. and Kumar, Jitender and Raut, D. and Shirame, S. and Makam, P. and Bhosale, R.},
   article_location = {Weinheim},
   article_number = {7},
   doi = {http://dx.doi.org/10.1002/ardp.202000003},
   keywords = {(E)-2-(2-allylidenehydrazinyl)thiazoles; anti-inflammatory; antituberculosis; radical scavenger; beta-ketoacyl-ACP synthase},
   language = {eng},
   issn = {0365-6233},
   journal = {Archiv der Pharmazie.},
   title = {(E)-2-(2-Allylidenehydrazinyl)thiazole derivatives: Design, green synthesis, in silico and in vitro antimycobacterial and radical scavenging studies},
   url = {https://onlinelibrary.wiley.com/doi/full/10.1002/ardp.202000003},
   volume = {353},
   year = {2020}
}

TY  - JOUR
ID  - 1752816
AU  - Hublikar, M. - Kadu, V. - Kumar, Jitender - Raut, D. - Shirame, S. - Makam, P. - Bhosale, R.
PY  - 2020
TI  - (E)-2-(2-Allylidenehydrazinyl)thiazole derivatives: Design, green synthesis, in silico and in vitro antimycobacterial and radical scavenging studies
JF  - Archiv der Pharmazie.
VL  - 353
IS  - 7
SP  - 2000003
EP  - 2000003
PB  - Verlag Chemie
SN  - 03656233
KW  - (E)-2-(2-allylidenehydrazinyl)thiazoles
KW  - anti-inflammatory
KW  - antituberculosis
KW  - radical scavenger
KW  - beta-ketoacyl-ACP synthase
UR  - https://onlinelibrary.wiley.com/doi/full/10.1002/ardp.202000003
N2  - By understanding the rampant infections of Mycobacterium tuberculosis (Mtb) and inflammations caused due to the generation of radical species during the Mtb infection, a series of (E)-2-(2-allylidenehydrazinyl)thiazole derivatives, with dual-action properties, was designed. The molecules were designed with a considerable variation in LogP, one of the critical parameters in physicochemical properties, and analyzed for their drug-likeness. For the synthesis, a simple, green, and multicomponent one-pot synthesis method was developed. The in vitro inhibition potentials were evaluated against Mtb H(37)Rv by the microplate Alamar Blue assay. The results reveal that compound 6 was potent, with a MIC value of 6.5 mu g/ml, and showed better interactions with the KasA protein with binding free energy (Delta G) of -9.4 kcal/mol. Also, the radical scavenging properties were studied to establish the dual-action properties of the molecules. Compound 9 exhibited promising antioxidant and nitric oxide radical scavenging activities, with 81.7% and 81.0%, respectively, at 1,000-mu g/ml concentration.
ER  -

HUBLIKAR, M., V. KADU, Jitender KUMAR, D. RAUT, S. SHIRAME, P. MAKAM and R. BHOSALE. (E)-2-(2-Allylidenehydrazinyl)thiazole derivatives: Design, green synthesis, in silico and in vitro antimycobacterial and radical scavenging studies. \textit{Archiv der Pharmazie.}. Weinheim: Verlag Chemie, 2020, vol.~353, No~7, p.~2000003-2000014. ISSN~0365-6233. Available from: https://dx.doi.org/10.1002/ardp.202000003.

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