Design, Synthesis, and Anti-mycobacterial Evaluation of New 3,5-Disubstituted-pyrazole-1-carbothioamides

Kok Tong Wong; Hasnah Osman; Thaigarajan Parumasivam; Muhammad Solehin Abd Ghani; Mohd Zaheen Hassan; Unang Supratman; Mohamad Nurul Azmi Mohamad Taib

doi:10.22146/ijc.70243

Design, Synthesis, and Anti-mycobacterial Evaluation of New 3,5-Disubstituted-pyrazole-1-carbothioamides

Kok Tong Wong, Hasnah Osman, Thaigarajan Parumasivam, Muhammad Solehin Abd Ghani, Mohd Zaheen Hassan, Unang Supratman, Mohamad Nurul Azmi Mohamad Taib^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

1 Scopus citations

Abstract

Two series of new 3,5-disubstituted-pyrazole-1-carbothioamides (4a-f and 5a-e) were designed and synthesized through condensation reaction between chalcones and thiosemicarbazides under alkaline condition via cyclocondensation reaction. The structures have been elucidated by Fourier-transform infrared (FTIR), High-resolution mass spectrometry (HRMS), one-and two-dimensional nuclear magnetic resonance (NMR) analyses. These compounds were assayed for in vitro anti-tuberculosis activity against Mycobacterium tuberculosis H37Ra using the Tetrazolium microplate assay (TEMA) method. As a result, six compounds (i.e., 4a, 4d, 4f, 5a, 5c, and 5d) showed a weak activity with minimum inhibition concentration (MIC) between 650–530 μM, and other compounds showed no inhibition against MTB. In addition, all tested compounds also did not show any cidal effects for minimum bactericidal concentration (MBC), even at the highest test concentration.

Original language	English
Pages (from-to)	703-713
Number of pages	11
Journal	Indonesian Journal of Chemistry
Volume	22
Issue number	3
DOIs	https://doi.org/10.22146/ijc.70243
State	Published - Jun 2022
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2022, Gadjah Mada University. All rights reserved.

Keywords

3,5-disubstituted-pyrazole-1-carbothioamide
Mycobacterium tuberculosis
anti-mycobacterial
antitubercular agents
pyrazolines

ASJC Scopus subject areas

General Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.22146/ijc.70243

Cite this

@article{4eb0a4c03c8e4fe786e339287aba39c6,

title = "Design, Synthesis, and Anti-mycobacterial Evaluation of New 3,5-Disubstituted-pyrazole-1-carbothioamides",

abstract = "Two series of new 3,5-disubstituted-pyrazole-1-carbothioamides (4a-f and 5a-e) were designed and synthesized through condensation reaction between chalcones and thiosemicarbazides under alkaline condition via cyclocondensation reaction. The structures have been elucidated by Fourier-transform infrared (FTIR), High-resolution mass spectrometry (HRMS), one-and two-dimensional nuclear magnetic resonance (NMR) analyses. These compounds were assayed for in vitro anti-tuberculosis activity against Mycobacterium tuberculosis H37Ra using the Tetrazolium microplate assay (TEMA) method. As a result, six compounds (i.e., 4a, 4d, 4f, 5a, 5c, and 5d) showed a weak activity with minimum inhibition concentration (MIC) between 650–530 μM, and other compounds showed no inhibition against MTB. In addition, all tested compounds also did not show any cidal effects for minimum bactericidal concentration (MBC), even at the highest test concentration.",

keywords = "3,5-disubstituted-pyrazole-1-carbothioamide, Mycobacterium tuberculosis, anti-mycobacterial, antitubercular agents, pyrazolines",

author = "Wong, \{Kok Tong\} and Hasnah Osman and Thaigarajan Parumasivam and Ghani, \{Muhammad Solehin Abd\} and Hassan, \{Mohd Zaheen\} and Unang Supratman and Taib, \{Mohamad Nurul Azmi Mohamad\}",

year = "2022",

month = jun,

doi = "10.22146/ijc.70243",

language = "English",

volume = "22",

pages = "703--713",

journal = "Indonesian Journal of Chemistry",

issn = "1411-9420",

publisher = "Gadjah Mada University",

number = "3",

}

TY - JOUR

T1 - Design, Synthesis, and Anti-mycobacterial Evaluation of New 3,5-Disubstituted-pyrazole-1-carbothioamides

AU - Wong, Kok Tong

AU - Osman, Hasnah

AU - Parumasivam, Thaigarajan

AU - Ghani, Muhammad Solehin Abd

AU - Hassan, Mohd Zaheen

AU - Supratman, Unang

AU - Taib, Mohamad Nurul Azmi Mohamad

PY - 2022/6

Y1 - 2022/6

N2 - Two series of new 3,5-disubstituted-pyrazole-1-carbothioamides (4a-f and 5a-e) were designed and synthesized through condensation reaction between chalcones and thiosemicarbazides under alkaline condition via cyclocondensation reaction. The structures have been elucidated by Fourier-transform infrared (FTIR), High-resolution mass spectrometry (HRMS), one-and two-dimensional nuclear magnetic resonance (NMR) analyses. These compounds were assayed for in vitro anti-tuberculosis activity against Mycobacterium tuberculosis H37Ra using the Tetrazolium microplate assay (TEMA) method. As a result, six compounds (i.e., 4a, 4d, 4f, 5a, 5c, and 5d) showed a weak activity with minimum inhibition concentration (MIC) between 650–530 μM, and other compounds showed no inhibition against MTB. In addition, all tested compounds also did not show any cidal effects for minimum bactericidal concentration (MBC), even at the highest test concentration.

AB - Two series of new 3,5-disubstituted-pyrazole-1-carbothioamides (4a-f and 5a-e) were designed and synthesized through condensation reaction between chalcones and thiosemicarbazides under alkaline condition via cyclocondensation reaction. The structures have been elucidated by Fourier-transform infrared (FTIR), High-resolution mass spectrometry (HRMS), one-and two-dimensional nuclear magnetic resonance (NMR) analyses. These compounds were assayed for in vitro anti-tuberculosis activity against Mycobacterium tuberculosis H37Ra using the Tetrazolium microplate assay (TEMA) method. As a result, six compounds (i.e., 4a, 4d, 4f, 5a, 5c, and 5d) showed a weak activity with minimum inhibition concentration (MIC) between 650–530 μM, and other compounds showed no inhibition against MTB. In addition, all tested compounds also did not show any cidal effects for minimum bactericidal concentration (MBC), even at the highest test concentration.

KW - 3,5-disubstituted-pyrazole-1-carbothioamide

KW - Mycobacterium tuberculosis

KW - anti-mycobacterial

KW - antitubercular agents

KW - pyrazolines

UR - https://www.scopus.com/pages/publications/85134345311

U2 - 10.22146/ijc.70243

DO - 10.22146/ijc.70243

M3 - Article

AN - SCOPUS:85134345311

SN - 1411-9420

VL - 22

SP - 703

EP - 713

JO - Indonesian Journal of Chemistry

JF - Indonesian Journal of Chemistry

IS - 3

ER -

Design, Synthesis, and Anti-mycobacterial Evaluation of New 3,5-Disubstituted-pyrazole-1-carbothioamides

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

UN SDGs

Access to Document

Fingerprint

Cite this