Antimycobacterial activity evaluation, time-kill kinetic and 3D-QSAR study of C-(3-aminomethyl-cyclohexyl)-methylamine derivatives

Deepak Kumar; K. Kranthi Raj; Maiann Bailey; Torey Alling; Tanya Parish; Diwan S. Rawat

doi:10.1016/j.bmcl.2012.12.083

Antimycobacterial activity evaluation, time-kill kinetic and 3D-QSAR study of C-(3-aminomethyl-cyclohexyl)-methylamine derivatives

Deepak Kumar
, K. Kranthi Raj
, Maiann Bailey
, Torey Alling
, Tanya Parish
, Diwan S. Rawat

University of Delhi
Infectious Disease Research Institute

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

19 Citations (Scopus)

Abstract

A series of C-(3-aminomethyl-cyclohexyl)-methylamine derivatives were synthesized and evaluated for their antitubercular activity. Some of the compounds exhibited potent activity against Mycobacterium tuberculosis H37Rv. One of the compound having t-butyl at para position of the benzene ring showed excellent activity even better than the standard drug ethambutol with MIC value 1.1 ± 0.2 μM. The time-kill kinetics study of two most active compounds showed rapid killing of the M. tuberculosis within 4 days. Additionally atom-based quantitative structure-activity relationship (QSAR) model was developed that gave a statistically satisfying result (R²) = 0.92, Q² = 0.75, Pearson-R = 0.96 and effectively predicts the anti-tuberculosis activity of training and test set compounds.

Original language	English
Pages (from-to)	1365-1369
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	23
Issue number	5
DOIs	https://doi.org/10.1016/j.bmcl.2012.12.083
Publication status	Published - 1 Mar 2013
Externally published	Yes

UN SDGs

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

SDG 3 Good Health and Well-being

Keywords

Bactericidal
Cyclohexane diamine
Mycobacterium tuberculosis H37Rv
QSAR
Tuberculosis

Access to Document

10.1016/j.bmcl.2012.12.083

Cite this

@article{36ece86396b0474b9172a79d898b31ee,

title = "Antimycobacterial activity evaluation, time-kill kinetic and 3D-QSAR study of C-(3-aminomethyl-cyclohexyl)-methylamine derivatives",

abstract = "A series of C-(3-aminomethyl-cyclohexyl)-methylamine derivatives were synthesized and evaluated for their antitubercular activity. Some of the compounds exhibited potent activity against Mycobacterium tuberculosis H37Rv. One of the compound having t-butyl at para position of the benzene ring showed excellent activity even better than the standard drug ethambutol with MIC value 1.1 ± 0.2 μM. The time-kill kinetics study of two most active compounds showed rapid killing of the M. tuberculosis within 4 days. Additionally atom-based quantitative structure-activity relationship (QSAR) model was developed that gave a statistically satisfying result (R2) = 0.92, Q2 = 0.75, Pearson-R = 0.96 and effectively predicts the anti-tuberculosis activity of training and test set compounds.",

keywords = "Bactericidal, Cyclohexane diamine, Mycobacterium tuberculosis H37Rv, QSAR, Tuberculosis",

author = "Deepak Kumar and Raj, \{K. Kranthi\} and Maiann Bailey and Torey Alling and Tanya Parish and Rawat, \{Diwan S.\}",

year = "2013",

month = mar,

day = "1",

doi = "10.1016/j.bmcl.2012.12.083",

language = "English",

volume = "23",

pages = "1365--1369",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Ltd",

number = "5",

}

TY - JOUR

T1 - Antimycobacterial activity evaluation, time-kill kinetic and 3D-QSAR study of C-(3-aminomethyl-cyclohexyl)-methylamine derivatives

AU - Kumar, Deepak

AU - Raj, K. Kranthi

AU - Bailey, Maiann

AU - Alling, Torey

AU - Parish, Tanya

AU - Rawat, Diwan S.

PY - 2013/3/1

Y1 - 2013/3/1

N2 - A series of C-(3-aminomethyl-cyclohexyl)-methylamine derivatives were synthesized and evaluated for their antitubercular activity. Some of the compounds exhibited potent activity against Mycobacterium tuberculosis H37Rv. One of the compound having t-butyl at para position of the benzene ring showed excellent activity even better than the standard drug ethambutol with MIC value 1.1 ± 0.2 μM. The time-kill kinetics study of two most active compounds showed rapid killing of the M. tuberculosis within 4 days. Additionally atom-based quantitative structure-activity relationship (QSAR) model was developed that gave a statistically satisfying result (R2) = 0.92, Q2 = 0.75, Pearson-R = 0.96 and effectively predicts the anti-tuberculosis activity of training and test set compounds.

AB - A series of C-(3-aminomethyl-cyclohexyl)-methylamine derivatives were synthesized and evaluated for their antitubercular activity. Some of the compounds exhibited potent activity against Mycobacterium tuberculosis H37Rv. One of the compound having t-butyl at para position of the benzene ring showed excellent activity even better than the standard drug ethambutol with MIC value 1.1 ± 0.2 μM. The time-kill kinetics study of two most active compounds showed rapid killing of the M. tuberculosis within 4 days. Additionally atom-based quantitative structure-activity relationship (QSAR) model was developed that gave a statistically satisfying result (R2) = 0.92, Q2 = 0.75, Pearson-R = 0.96 and effectively predicts the anti-tuberculosis activity of training and test set compounds.

KW - Bactericidal

KW - Cyclohexane diamine

KW - Mycobacterium tuberculosis H37Rv

KW - QSAR

KW - Tuberculosis

U2 - 10.1016/j.bmcl.2012.12.083

DO - 10.1016/j.bmcl.2012.12.083

M3 - Article

C2 - 23357633

AN - SCOPUS:84873741214

SN - 0960-894X

VL - 23

SP - 1365

EP - 1369

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 5

ER -

Antimycobacterial activity evaluation, time-kill kinetic and 3D-QSAR study of C-(3-aminomethyl-cyclohexyl)-methylamine derivatives

Abstract

UN SDGs

Keywords

Access to Document

Fingerprint

Cite this