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Title:
Synthesis and anticancer activity of novel fused pyrimidine hybrids of myrrhanone C, a bicyclic triterpene of Commiphora mukul gum resin | Molecular Diversity
Description:
Abstract Myrrhanone C [8(R)-3-oxo-8-hydroxypolypoda-13E,17E,21-triene], a bicyclic triterpene isolated from the gum resin of Commiphora mukul, has been chemically transformed to synthesize a series of ten novel pyrimidine hybrids in good to excellent yields. The synthesized compounds (2–22) were evaluated for their anticancer potential against a panel of six cancer cell lines, namely A-549 (lung), Hela (cervical), MCF-7 (breast), ACHN (renal), Colo-205 (colon) and B-16 (mouse melanoma) by employing the MTT assay. In general, the synthesized compounds showed significant anticancer activity against all the cancer cell lines tested. Interestingly, the pyrimidine hybrids 18 and 19 showed good activity against the A-549, MCF-7, B-16, Colo-205 and ACHN cancer cell lines with $$\hbox {IC}_{50}$$ IC 50 values between 7.7–37.8 $$\upmu $$ μ M. Most significantly, compounds 19 (IC $$_{50}$$ 50 : 7.7 $$\upmu $$ μ M) and 18 (IC $$_{50}$$ 50 : 9.5 $$\upmu $$ μ M) showed about five- and six-fold enhanced activities, respectively, compared to the parent myrrhanone C (1) against A-549 cell line. Flow cytometric analysis revealed that compounds 18 and 19 induced apoptosis in A-549 cells and arrested the cell growth in the G0/G1 phase. Graphical Abstract
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article, google, scholar, cas, pubmed, synthesis, cancer, chem, cell, anticancer, activity, resin, apoptosis, pyrimidine, hybrids, myrrhanone, med, mukul, mallavadhani, lines, privacy, cookies, content, commiphora, gum, ramakrishna, compounds, products, publish, search, fused, bicyclic, triterpene, nayak, activities, access, drug, chemistry, bioorg, derivatives, india, data, information, log, journal, research, molecular, uppuluri, venkata, chandrashekhar,
Topics {✒️}
month download article/chapter uppuluri venkata mallavadhani arrest cell cycle anti-prostate cancer lead structure–activity relationship study full article pdf potential anti-inflammatory interest myrrh-commiphora chemistry medicinal chemistry guggul-gum resin cisplatin-induced apoptosis proceeds cancer cell lines 6-substituted-pyrimidines & 4-styryl-6 privacy choices/manage cookies fold enhanced activities article mallavadhani structure–activity relationship lakshma nayak anti-inflammatory activity anti-cancer activity guggul-gum resins related subjects flow cytometric detection sistla ramakrishna gum resin a-549 cell line potential anticancer agents synthesized 4h-chromene commiphora mukul european economic area g0/g1 phase sung ramaswamy bk octanordammarane-type triterpenes hiv-1 ltr activation situ dna degradation subba rao av ] indolone–pyrrolobenzodiazepine conjugates etoposide-induced apoptosis targeting inflammatory pathways heterocyclic systems fused fused pyrimidine hybrids condensed pyrimidine-thiones conditions privacy policy pharmaceutically valuable compounds 3-oxo-8-hydroxypolypoda-13e breast cancer cells electronic supplementary material anticancer activity article log accepting optional cookies
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headline:Synthesis and anticancer activity of novel fused pyrimidine hybrids of myrrhanone C, a bicyclic triterpene of Commiphora mukul gum resin
description:Myrrhanone C [8(R)-3-oxo-8-hydroxypolypoda-13E,17E,21-triene], a bicyclic triterpene isolated from the gum resin of Commiphora mukul, has been chemically transformed to synthesize a series of ten novel pyrimidine hybrids in good to excellent yields. The synthesized compounds (2–22) were evaluated for their anticancer potential against a panel of six cancer cell lines, namely A-549 (lung), Hela (cervical), MCF-7 (breast), ACHN (renal), Colo-205 (colon) and B-16 (mouse melanoma) by employing the MTT assay. In general, the synthesized compounds showed significant anticancer activity against all the cancer cell lines tested. Interestingly, the pyrimidine hybrids 18 and 19 showed good activity against the A-549, MCF-7, B-16, Colo-205 and ACHN cancer cell lines with
$$\hbox {IC}_{50}$$
values between 7.7–37.8
$$\upmu $$
M. Most significantly, compounds 19 (IC
$$_{50}$$
: 7.7
$$\upmu $$
M) and 18 (IC
$$_{50}$$
: 9.5
$$\upmu $$
M) showed about five- and six-fold enhanced activities, respectively, compared to the parent myrrhanone C (1) against A-549 cell line. Flow cytometric analysis revealed that compounds 18 and 19 induced apoptosis in A-549 cells and arrested the cell growth in the G0/G1 phase.
datePublished:2015-08-01T00:00:00Z
dateModified:2015-08-01T00:00:00Z
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Myrrhanone C
Pyrimidines
Hybrids
Anticancer activity
Apoptosis
Cell cycle arrest
Biochemistry
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Polymer Sciences
Pharmacy
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headline:Synthesis and anticancer activity of novel fused pyrimidine hybrids of myrrhanone C, a bicyclic triterpene of Commiphora mukul gum resin
description:Myrrhanone C [8(R)-3-oxo-8-hydroxypolypoda-13E,17E,21-triene], a bicyclic triterpene isolated from the gum resin of Commiphora mukul, has been chemically transformed to synthesize a series of ten novel pyrimidine hybrids in good to excellent yields. The synthesized compounds (2–22) were evaluated for their anticancer potential against a panel of six cancer cell lines, namely A-549 (lung), Hela (cervical), MCF-7 (breast), ACHN (renal), Colo-205 (colon) and B-16 (mouse melanoma) by employing the MTT assay. In general, the synthesized compounds showed significant anticancer activity against all the cancer cell lines tested. Interestingly, the pyrimidine hybrids 18 and 19 showed good activity against the A-549, MCF-7, B-16, Colo-205 and ACHN cancer cell lines with
$$\hbox {IC}_{50}$$
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$$\upmu $$
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$$\upmu $$
M) and 18 (IC
$$_{50}$$
: 9.5
$$\upmu $$
M) showed about five- and six-fold enhanced activities, respectively, compared to the parent myrrhanone C (1) against A-549 cell line. Flow cytometric analysis revealed that compounds 18 and 19 induced apoptosis in A-549 cells and arrested the cell growth in the G0/G1 phase.
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Pyrimidines
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Anticancer activity
Apoptosis
Cell cycle arrest
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general
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Pharmacy
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