Hexafluoroisopropanol-Mediated Domino Reaction for the Synthesis of Thiazolo-androstenones: Potent Anticancer Agents

Christina Okolo; Mohamad Akbar Ali; Matthew Newman; Steven A. Chambers; Jedidiah Whitt; Zakeyah A. Alsharif; Victor W. Day; Mohammad A. Alam

doi:10.1021/acsomega.8b02840

Hexafluoroisopropanol-Mediated Domino Reaction for the Synthesis of Thiazolo-androstenones: Potent Anticancer Agents

Christina Okolo
, Mohamad Akbar Ali
, Matthew Newman
, Steven A. Chambers
, Jedidiah Whitt
, Zakeyah A. Alsharif
, Victor W. Day
, Mohammad A. Alam

Chemistry

Arkansas State University
The University of Kansas

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

15 Scopus citations

Abstract

A cascade reaction of thioamides with 6β-bromoandrostenedione in hexafluoroisopropanol formed substituted thiazolo-androstenones. This is a simple and mild protocol to synthesize novel molecules by using readily available reagents and substrates. Feasibility of the reaction has been rationalized by density functional theory calculations. Moreover, these compounds are potent growth inhibitors of colon, central nervous system, melanoma, ovarian, and renal cancer cell lines with 50% growth inhibition values as low as 1.04 μM.

Original language	British English
Pages (from-to)	17991-18001
Number of pages	11
Journal	ACS Omega
Volume	3
Issue number	12
DOIs	https://doi.org/10.1021/acsomega.8b02840
State	Published - 21 Dec 2018

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10.1021/acsomega.8b02840

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@article{2b8a0a3aeb3b4c69be949dc2d4c18a3b,

title = "Hexafluoroisopropanol-Mediated Domino Reaction for the Synthesis of Thiazolo-androstenones: Potent Anticancer Agents",

abstract = "A cascade reaction of thioamides with 6β-bromoandrostenedione in hexafluoroisopropanol formed substituted thiazolo-androstenones. This is a simple and mild protocol to synthesize novel molecules by using readily available reagents and substrates. Feasibility of the reaction has been rationalized by density functional theory calculations. Moreover, these compounds are potent growth inhibitors of colon, central nervous system, melanoma, ovarian, and renal cancer cell lines with 50\% growth inhibition values as low as 1.04 μM.",

author = "Christina Okolo and Ali, \{Mohamad Akbar\} and Matthew Newman and Chambers, \{Steven A.\} and Jedidiah Whitt and Alsharif, \{Zakeyah A.\} and Day, \{Victor W.\} and Alam, \{Mohammad A.\}",

note = "Funding Information: We are thankful to the INBRE for a pilot grant (grant \#224658) and ABI mini-grant 200138. 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 crystal structure of compounds. M.A.A. thanks National Research Foundation of South Korea for the financial support. Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

month = dec,

day = "21",

doi = "10.1021/acsomega.8b02840",

language = "British English",

volume = "3",

pages = "17991--18001",

journal = "ACS Omega",

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}

TY - JOUR

T1 - Hexafluoroisopropanol-Mediated Domino Reaction for the Synthesis of Thiazolo-androstenones

T2 - Potent Anticancer Agents

AU - Okolo, Christina

AU - Ali, Mohamad Akbar

AU - Newman, Matthew

AU - Chambers, Steven A.

AU - Whitt, Jedidiah

AU - Alsharif, Zakeyah A.

AU - Day, Victor W.

AU - Alam, Mohammad A.

N1 - Funding Information: We are thankful to the INBRE for a pilot grant (grant #224658) and ABI mini-grant 200138. 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 crystal structure of compounds. M.A.A. thanks National Research Foundation of South Korea for the financial support. Publisher Copyright: © 2018 American Chemical Society.

PY - 2018/12/21

Y1 - 2018/12/21

N2 - A cascade reaction of thioamides with 6β-bromoandrostenedione in hexafluoroisopropanol formed substituted thiazolo-androstenones. This is a simple and mild protocol to synthesize novel molecules by using readily available reagents and substrates. Feasibility of the reaction has been rationalized by density functional theory calculations. Moreover, these compounds are potent growth inhibitors of colon, central nervous system, melanoma, ovarian, and renal cancer cell lines with 50% growth inhibition values as low as 1.04 μM.

AB - A cascade reaction of thioamides with 6β-bromoandrostenedione in hexafluoroisopropanol formed substituted thiazolo-androstenones. This is a simple and mild protocol to synthesize novel molecules by using readily available reagents and substrates. Feasibility of the reaction has been rationalized by density functional theory calculations. Moreover, these compounds are potent growth inhibitors of colon, central nervous system, melanoma, ovarian, and renal cancer cell lines with 50% growth inhibition values as low as 1.04 μM.

UR - https://www.scopus.com/pages/publications/85059217621

U2 - 10.1021/acsomega.8b02840

DO - 10.1021/acsomega.8b02840

M3 - Article

AN - SCOPUS:85059217621

SN - 2470-1343

VL - 3

SP - 17991

EP - 18001

JO - ACS Omega

JF - ACS Omega

IS - 12

ER -

Hexafluoroisopropanol-Mediated Domino Reaction for the Synthesis of Thiazolo-androstenones: Potent Anticancer Agents

Abstract

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