Microwave assisted synthesis and in vitro cytotoxicities of substituted (Z)-2-amino-5-(1-benzyl-1H-indol-3-yl)methylene-1-methyl-1H-imidazol-4(5H)-ones against human tumor cell lines

Penthala, Narsimha Reddy; Yerramreddy, Thirupathi Reddy; Crooks, Peter A.

doi:10.1016/j.bmcl.2009.11.083

Cited by 23 publications

(6 citation statements)

References 8 publications

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“…1), 1 and we have also described the radiosensitizing activity of some related N -benzylindole analogs ( B , Fig. 1) in parallel with their cytotoxic properties.…”

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confidence: 53%

5-((1-Aroyl-1H-indol-3-yl)methylene)-2-thioxodihydropyrimidine-4,6(1H,5H)-diones as potential anticancer agents with anti-inflammatory properties

Penthala

Ponugoti

Kasam

et al. 2013

Bioorganic & Medicinal Chemistry Letters

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A series of novel 5-((1-aroyl-1H-indol-3-yl)methylene)-2-thioxodihydropyrimidine-4,6(1H,5H)-diones (3a–z) have been evaluated for in vitro cytotoxicity against a panel of 60 human tumor cell lines. Compound 3k exhibited the most potent growth inhibition against melanoma MDA-MB-435 cells (GI50=850 nM), against leukemia SR cancer cells (GI50=1.45 μM), and OVCAR-3 (GI50=1.26 μM) ovarian cancer cell lines The structurally related compound 3s had a GI50 value of 1.77 μM against MDA-MB-435 cells The N-naphthoyl analogue 3t had GI50 values of 1.30 μM and 1.91 μM against HOP-92 non-small cell lung cancer and MDA-MB-435 melanoma cell lines, respectively. The related analogue 3w had GI50 values of 1.09 μM against HOP-92 non-small cell lung cancer cell lines. Interestingly, docking of the two active molecules 3k and 3w into the active site of COX-2 indicates that these compounds are COX-2 ligands with strong hydrophobic and hydrogen bonding interactions. Thus, compounds 3k, 3t, 3s, and 3w constitute a new class of anticancer/anti-inflammatory agents that may have unique potential for cancer therapy.

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“…1), 1 and we have also described the radiosensitizing activity of some related N -benzylindole analogs ( B , Fig. 1) in parallel with their cytotoxic properties.…”

mentioning

confidence: 53%

5-((1-Aroyl-1H-indol-3-yl)methylene)-2-thioxodihydropyrimidine-4,6(1H,5H)-diones as potential anticancer agents with anti-inflammatory properties

Penthala

Ponugoti

Kasam

et al. 2013

Bioorganic & Medicinal Chemistry Letters

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“…This synthesis has since been used to make a variety of analogues, 117,125 including 5,6-dibromo-2′-demethylaplysinopsin 126 and several series of N-alkylated aplysinopsin derivatives used for biological testing. [127][128][129] The conditions for this reaction vary but typically require heat and addition of a base, such as piperidine. A microwave-assisted method has been reported as well, where the reaction was microwaved for 30-60 seconds with creatinine and NaOAc.…”

Section: (4h)-imidazol-4-one Containing Natural Products and Their Total Synthesesmentioning

confidence: 99%

The preparation of (4H)-imidazol-4-ones and their application in the total synthesis of natural products

Keel

Tepe

2020

Org. Chem. Front.

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“…Structure B ). 8 In this respect, Li et al have synthesized and studied a series of structurally related N -heterocyclic indolyl glyoxylamides (Fig 1 . Structure C ), and found that such compounds possess marked activity against several cancer cell lines, including multidrug resistance (MDR) cell lines.…”

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confidence: 99%

Synthesis and in vitro screening of novel N-benzyl aplysinopsin analogs as potential anticancer agents

Penthala

Yerramreddy

Crooks

2011

Bioorganic & Medicinal Chemistry Letters

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A series of novel substituted (Z)-methyl 1-benzyl-3-((2,5-dioxoimidazolidin-4-ylidene)methyl)-1H-indoles (3a-f) and (Z)-5-((1-benzyl-1H-indol-3-yl)methylene)thiazolidine-2,4-diones (3g-o) have been synthesized utilizing microwave irradiation. These analogs were evaluated for in vitro cytotoxicity against a panel of 60 human tumor cell lines. Compound 3i exhibits potent growth inhibition against melanoma UACC-257 (GI50=13.3 nM) and OVCAR-8 ovarian (GI50=19.5 nM) cancer cells while possessing significant cytotoxicity (LC50=308 nM and LC50=851 nM, respectively) against the same cell lines within this series of compounds. A second analog, 3a, had GI50 values of 307 nM and 557 nM against SK-MEL-2 melanoma and A498 renal cancer cell lines, and exhibited GI50 values ranging from 0.30-6 µM against 98% of all cancer cell lines in the 60-cell panel. Thus, (Z)-5-((5-chloro-1-(4-fluorobenzyl)-1H-indol-3-yl)methylene)-2-iminothiazolidin-4-one (3i) and (Z)-methyl 1-(4-cyanobenzyl)-3-((2,5-dioxoimidazolidin-4-ylidene)methyl)-1H-indole-6-carboxylate (3a) can be regarded as useful lead compounds for further structural optimization as antitumor agents.

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Microwave assisted synthesis and in vitro cytotoxicities of substituted (Z)-2-amino-5-(1-benzyl-1H-indol-3-yl)methylene-1-methyl-1H-imidazol-4(5H)-ones against human tumor cell lines

Cited by 23 publications

References 8 publications

5-((1-Aroyl-1H-indol-3-yl)methylene)-2-thioxodihydropyrimidine-4,6(1H,5H)-diones as potential anticancer agents with anti-inflammatory properties

5-((1-Aroyl-1H-indol-3-yl)methylene)-2-thioxodihydropyrimidine-4,6(1H,5H)-diones as potential anticancer agents with anti-inflammatory properties

The preparation of (4H)-imidazol-4-ones and their application in the total synthesis of natural products

Synthesis and in vitro screening of novel N-benzyl aplysinopsin analogs as potential anticancer agents

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