Benign Synthesis of Thiazolo-androstenone Derivatives as Potent Anticancer Agents

Mohamad Akbar Ali; Christina Okolo; Zakeyah A. Alsharif; Jedidiah Whitt; Steven A. Chambers; Rajender S. Varma; Mohammad A. Alam

doi:10.1021/acs.orglett.8b02587

Benign Synthesis of Thiazolo-androstenone Derivatives as Potent Anticancer Agents

Mohamad Akbar Ali
, Christina Okolo
, Zakeyah A. Alsharif
, Jedidiah Whitt
, Steven A. Chambers
, Rajender S. Varma
, Mohammad A. Alam

Chemistry

Arkansas State University
Palacky University

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

23 Scopus citations

Abstract

An unprecedented reaction of thiourea derivatives with 6β-bromoandrostenedione has been discovered for the formation of aminothiazolo-androstenones via a simple, safer, cascade protocol that enables the syntheses of novel molecules by using readily available reagents. The reaction mechanism of product formation has been rationalized by density functional theory calculations. This benign methodology accentuates a domino protocol deploying a renewable solvent, ethanol, while generating novel compounds that display potent growth inhibitory effects in in vitro studies for several cancer cell lines at submicromolar concentrations.

Original language	British English
Pages (from-to)	5927-5932
Number of pages	6
Journal	Organic Letters
Volume	20
Issue number	18
DOIs	https://doi.org/10.1021/acs.orglett.8b02587
State	Published - 21 Sep 2018

UN SDGs

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

SDG 3 Good Health and Well-being

Access to Document

10.1021/acs.orglett.8b02587

OpenUrl availability

Full text

Cite this

@article{51e966b0cc94408eb01c82c42d681f92,

title = "Benign Synthesis of Thiazolo-androstenone Derivatives as Potent Anticancer Agents",

abstract = "An unprecedented reaction of thiourea derivatives with 6β-bromoandrostenedione has been discovered for the formation of aminothiazolo-androstenones via a simple, safer, cascade protocol that enables the syntheses of novel molecules by using readily available reagents. The reaction mechanism of product formation has been rationalized by density functional theory calculations. This benign methodology accentuates a domino protocol deploying a renewable solvent, ethanol, while generating novel compounds that display potent growth inhibitory effects in in vitro studies for several cancer cell lines at submicromolar concentrations.",

author = "Ali, \{Mohamad Akbar\} and Christina Okolo and Alsharif, \{Zakeyah A.\} and Jedidiah Whitt and Chambers, \{Steven A.\} and Varma, \{Rajender S.\} and Alam, \{Mohammad A.\}",

note = "Funding Information: We are thankful to the INBRE for a pilot grant (Grant No. 224658). This publication was made possible by the Research Technology Core of the Arkansas INBRE Program, supported by a grant from the National Institute of General Medical Sciences, (NIGMS), P20 GM103429-16, from the National Institutes of Health to record the mass spectrometry data. We are thankful to Dr. Victor, Director/Senior Scientist X-ray Crystallography Laboratory University of Kansas (NSF-MRI grant CHE-0923449), for recording the crystal structures of compounds. Publisher Copyright: Copyright {\textcopyright} 2018 American Chemical Society.",

year = "2018",

month = sep,

day = "21",

doi = "10.1021/acs.orglett.8b02587",

language = "British English",

volume = "20",

pages = "5927--5932",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "18",

}

TY - JOUR

T1 - Benign Synthesis of Thiazolo-androstenone Derivatives as Potent Anticancer Agents

AU - Ali, Mohamad Akbar

AU - Okolo, Christina

AU - Alsharif, Zakeyah A.

AU - Whitt, Jedidiah

AU - Chambers, Steven A.

AU - Varma, Rajender S.

AU - Alam, Mohammad A.

N1 - Funding Information: We are thankful to the INBRE for a pilot grant (Grant No. 224658). This publication was made possible by the Research Technology Core of the Arkansas INBRE Program, supported by a grant from the National Institute of General Medical Sciences, (NIGMS), P20 GM103429-16, from the National Institutes of Health to record the mass spectrometry data. We are thankful to Dr. Victor, Director/Senior Scientist X-ray Crystallography Laboratory University of Kansas (NSF-MRI grant CHE-0923449), for recording the crystal structures of compounds. Publisher Copyright: Copyright © 2018 American Chemical Society.

PY - 2018/9/21

Y1 - 2018/9/21

N2 - An unprecedented reaction of thiourea derivatives with 6β-bromoandrostenedione has been discovered for the formation of aminothiazolo-androstenones via a simple, safer, cascade protocol that enables the syntheses of novel molecules by using readily available reagents. The reaction mechanism of product formation has been rationalized by density functional theory calculations. This benign methodology accentuates a domino protocol deploying a renewable solvent, ethanol, while generating novel compounds that display potent growth inhibitory effects in in vitro studies for several cancer cell lines at submicromolar concentrations.

AB - An unprecedented reaction of thiourea derivatives with 6β-bromoandrostenedione has been discovered for the formation of aminothiazolo-androstenones via a simple, safer, cascade protocol that enables the syntheses of novel molecules by using readily available reagents. The reaction mechanism of product formation has been rationalized by density functional theory calculations. This benign methodology accentuates a domino protocol deploying a renewable solvent, ethanol, while generating novel compounds that display potent growth inhibitory effects in in vitro studies for several cancer cell lines at submicromolar concentrations.

UR - https://www.scopus.com/pages/publications/85053604650

U2 - 10.1021/acs.orglett.8b02587

DO - 10.1021/acs.orglett.8b02587

M3 - Article

C2 - 30204455

AN - SCOPUS:85053604650

SN - 1523-7060

VL - 20

SP - 5927

EP - 5932

JO - Organic Letters

JF - Organic Letters

IS - 18

ER -

Benign Synthesis of Thiazolo-androstenone Derivatives as Potent Anticancer Agents

Abstract

UN SDGs

Access to Document

OpenUrl availability

Other files and links

Fingerprint

Cite this