Aplysinopsin analogs: Synthesis and anti-proliferative activity of substituted (Z)-5-(N-benzylindol-3-ylmethylene)imidazolidine-2,4-diones

Y. Thirupathi Reddy; P. Narsimha Reddy; Srinivas Koduru; Chendil Damodaran; Peter A. Crooks

doi:10.1016/j.bmc.2010.03.054

Aplysinopsin analogs: Synthesis and anti-proliferative activity of substituted (Z)-5-(N-benzylindol-3-ylmethylene)imidazolidine-2,4-diones

Y. Thirupathi Reddy
, P. Narsimha Reddy
, Srinivas Koduru
, Chendil Damodaran
, Peter A. Crooks

Department of Surgery

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

37 Scopus citations

Abstract

A series of substituted (Z)-5-(N-benzylindol-3-ylmethylene)imidazolidine-2,4-dione (3) analogs structurally related to aplysinopsin, and that incorporate a variety of substituents in both the indole and N-benzyl moieties have been synthesized under microwave irradiation and conventional heating methods These analogs were evaluated for their anti-proliferative activity against MCF-7 and MDA-231 breast cancer cell lines, and A549 and H460 lung cancer cell lines. Two analogs, 3f and 3j had IC₅₀ values of 4.4 and 5.2 μM, respectively, compared to 5-fluorouracil (IC₅₀ = 15.2 μM) against MCF-7 cells.

Original language	English (US)
Pages (from-to)	3570-3574
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry
Volume	18
Issue number	10
DOIs	https://doi.org/10.1016/j.bmc.2010.03.054
State	Published - May 15 2010

All Science Journal Classification (ASJC) codes

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmc.2010.03.054

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title = "Aplysinopsin analogs: Synthesis and anti-proliferative activity of substituted (Z)-5-(N-benzylindol-3-ylmethylene)imidazolidine-2,4-diones",

abstract = "A series of substituted (Z)-5-(N-benzylindol-3-ylmethylene)imidazolidine-2,4-dione (3) analogs structurally related to aplysinopsin, and that incorporate a variety of substituents in both the indole and N-benzyl moieties have been synthesized under microwave irradiation and conventional heating methods These analogs were evaluated for their anti-proliferative activity against MCF-7 and MDA-231 breast cancer cell lines, and A549 and H460 lung cancer cell lines. Two analogs, 3f and 3j had IC50 values of 4.4 and 5.2 μM, respectively, compared to 5-fluorouracil (IC50 = 15.2 μM) against MCF-7 cells.",

author = "\{Thirupathi Reddy\}, Y. and \{Narsimha Reddy\}, P. and Srinivas Koduru and Chendil Damodaran and Crooks, \{Peter A.\}",

note = "Funding Information: This research was supported by NIH/National Cancer Institute Grant PO1 CA104457 . ",

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doi = "10.1016/j.bmc.2010.03.054",

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T2 - Synthesis and anti-proliferative activity of substituted (Z)-5-(N-benzylindol-3-ylmethylene)imidazolidine-2,4-diones

AU - Thirupathi Reddy, Y.

AU - Narsimha Reddy, P.

AU - Koduru, Srinivas

AU - Damodaran, Chendil

AU - Crooks, Peter A.

N1 - Funding Information: This research was supported by NIH/National Cancer Institute Grant PO1 CA104457 .

PY - 2010/5/15

Y1 - 2010/5/15

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AB - A series of substituted (Z)-5-(N-benzylindol-3-ylmethylene)imidazolidine-2,4-dione (3) analogs structurally related to aplysinopsin, and that incorporate a variety of substituents in both the indole and N-benzyl moieties have been synthesized under microwave irradiation and conventional heating methods These analogs were evaluated for their anti-proliferative activity against MCF-7 and MDA-231 breast cancer cell lines, and A549 and H460 lung cancer cell lines. Two analogs, 3f and 3j had IC50 values of 4.4 and 5.2 μM, respectively, compared to 5-fluorouracil (IC50 = 15.2 μM) against MCF-7 cells.

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DO - 10.1016/j.bmc.2010.03.054

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AN - SCOPUS:77953136824

SN - 0968-0896

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Aplysinopsin analogs: Synthesis and anti-proliferative activity of substituted (Z)-5-(N-benzylindol-3-ylmethylene)imidazolidine-2,4-diones

Abstract

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