Synthesis, characterization, bioactivity, and POM analyses of isothiochromeno[3,4-e][1,2]oxazines

Brahim Bennani; Abdelali Kerbal; Bouchra F. Baba; Maria Daoudi; Ismail Warad; Mohamad Aljofan; Ahmed M. Alafeefy; Vijay Masand; Taibi B. Hadda

doi:10.1007/s00044-012-0392-4

Synthesis, characterization, bioactivity, and POM analyses of isothiochromeno[3,4-e][1,2]oxazines

Brahim Bennani, Abdelali Kerbal, Bouchra F. Baba, Maria Daoudi, Ismail Warad, Mohamad Aljofan, Ahmed M. Alafeefy, Vijay Masand, Taibi B. Hadda

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

4 Citations (Scopus)

Abstract

A series of 18 new 3,4-disubstituted-isothiochromeno[3,4-e][1,2]oxazines 28-45 has been obtained from the 3′,4′-di-substituted-4′H- spiro[isothiochromene-3,5′-isoxazol]-4(1H)-ones 10-27 in refluxing HCl acid/ethanol. A series of 15/18 compounds 28-45 was selected by the National Cancer Institute (NCI, Bethesda, USA) and were evaluated against a full panel of 60 primary human tumor cell lines derived from nine human cancer types, all of which showed antiproliferative activity in the micromolar range. The most active compound number 37 (S722910) showed high potency against all the tested cell lines with a GI₅₀ mean value in the range of 30-80 μM; TGI and LC₅₀ values were 12-16 μM having positive response on 98 and 63 % of the tested cell lines (Breast-MCF7 and NCS-SF-268) respectively. Graphical Abstract: [Figure not available: see fulltext.]

Original language	English
Pages (from-to)	4798-4809
Number of pages	12
Journal	Medicinal Chemistry Research
Volume	22
Issue number	10
DOIs	https://doi.org/10.1007/s00044-012-0392-4
Publication status	Published - Oct 1 2013
Externally published	Yes

Keywords

Breast cancer inhibition
Leukemia
POM analyses
Spiro-isothiochromeno[3,4-e][1,2] oxazines

ASJC Scopus subject areas

Pharmacology, Toxicology and Pharmaceutics(all)
Organic Chemistry

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Synthesis, characterization, bioactivity, and POM analyses of isothiochromeno[3,4-e][1,2]oxazines. / Bennani, Brahim; Kerbal, Abdelali; Baba, Bouchra F.; Daoudi, Maria; Warad, Ismail; Aljofan, Mohamad; Alafeefy, Ahmed M.; Masand, Vijay; Hadda, Taibi B.

In: Medicinal Chemistry Research, Vol. 22, No. 10, 01.10.2013, p. 4798-4809.

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

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title = "Synthesis, characterization, bioactivity, and POM analyses of isothiochromeno[3,4-e][1,2]oxazines",

abstract = "A series of 18 new 3,4-disubstituted-isothiochromeno[3,4-e][1,2]oxazines 28-45 has been obtained from the 3′,4′-di-substituted-4′H- spiro[isothiochromene-3,5′-isoxazol]-4(1H)-ones 10-27 in refluxing HCl acid/ethanol. A series of 15/18 compounds 28-45 was selected by the National Cancer Institute (NCI, Bethesda, USA) and were evaluated against a full panel of 60 primary human tumor cell lines derived from nine human cancer types, all of which showed antiproliferative activity in the micromolar range. The most active compound number 37 (S722910) showed high potency against all the tested cell lines with a GI50 mean value in the range of 30-80 μM; TGI and LC50 values were 12-16 μM having positive response on 98 and 63 % of the tested cell lines (Breast-MCF7 and NCS-SF-268) respectively. Graphical Abstract: [Figure not available: see fulltext.]",

keywords = "Breast cancer inhibition, Leukemia, POM analyses, Spiro-isothiochromeno[3,4-e][1,2] oxazines",

author = "Brahim Bennani and Abdelali Kerbal and Baba, {Bouchra F.} and Maria Daoudi and Ismail Warad and Mohamad Aljofan and Alafeefy, {Ahmed M.} and Vijay Masand and Hadda, {Taibi B.}",

note = "Funding Information: Acknowledgments This work was supported by the grants from the Ministry of Education of Morocco (PGR-UMP-BH-2005 and PRO-TARS I). We are indebted to the National Cancer Institute (NCI) of the United States for biologic tests.",

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T1 - Synthesis, characterization, bioactivity, and POM analyses of isothiochromeno[3,4-e][1,2]oxazines

AU - Bennani, Brahim

AU - Kerbal, Abdelali

AU - Baba, Bouchra F.

AU - Daoudi, Maria

AU - Warad, Ismail

AU - Aljofan, Mohamad

AU - Alafeefy, Ahmed M.

AU - Masand, Vijay

AU - Hadda, Taibi B.

N1 - Funding Information: Acknowledgments This work was supported by the grants from the Ministry of Education of Morocco (PGR-UMP-BH-2005 and PRO-TARS I). We are indebted to the National Cancer Institute (NCI) of the United States for biologic tests.

PY - 2013/10/1

Y1 - 2013/10/1

N2 - A series of 18 new 3,4-disubstituted-isothiochromeno[3,4-e][1,2]oxazines 28-45 has been obtained from the 3′,4′-di-substituted-4′H- spiro[isothiochromene-3,5′-isoxazol]-4(1H)-ones 10-27 in refluxing HCl acid/ethanol. A series of 15/18 compounds 28-45 was selected by the National Cancer Institute (NCI, Bethesda, USA) and were evaluated against a full panel of 60 primary human tumor cell lines derived from nine human cancer types, all of which showed antiproliferative activity in the micromolar range. The most active compound number 37 (S722910) showed high potency against all the tested cell lines with a GI50 mean value in the range of 30-80 μM; TGI and LC50 values were 12-16 μM having positive response on 98 and 63 % of the tested cell lines (Breast-MCF7 and NCS-SF-268) respectively. Graphical Abstract: [Figure not available: see fulltext.]

AB - A series of 18 new 3,4-disubstituted-isothiochromeno[3,4-e][1,2]oxazines 28-45 has been obtained from the 3′,4′-di-substituted-4′H- spiro[isothiochromene-3,5′-isoxazol]-4(1H)-ones 10-27 in refluxing HCl acid/ethanol. A series of 15/18 compounds 28-45 was selected by the National Cancer Institute (NCI, Bethesda, USA) and were evaluated against a full panel of 60 primary human tumor cell lines derived from nine human cancer types, all of which showed antiproliferative activity in the micromolar range. The most active compound number 37 (S722910) showed high potency against all the tested cell lines with a GI50 mean value in the range of 30-80 μM; TGI and LC50 values were 12-16 μM having positive response on 98 and 63 % of the tested cell lines (Breast-MCF7 and NCS-SF-268) respectively. Graphical Abstract: [Figure not available: see fulltext.]

KW - Breast cancer inhibition

KW - Leukemia

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KW - Spiro-isothiochromeno[3,4-e][1,2] oxazines

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