Design and synthesis of new 2,5-disubstituted-1,3,4-oxadiazole analogues as anticancer agents

Agarwal, Mohit; Singh, Vikram; Kumar, Manish; Sharma, Pooja; Ansari, Yousuf; Jadav, Surender Singh; Yasmin, Sabina; Sreenivasulu, Reddymasu; Hassan, Mohd. Zaheen; Saini, Vipin; Ahsan, Mohamed Jawed

doi:10.1007/s00044-016-1672-1

Cited by 59 publications

(23 citation statements)

References 17 publications

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“…Furthermore introduction of the methylene (-CH 2 -) linkage was found to be promising and increased the anticancer activity not in the present study but also reported in the earlier work. [22] However further investigation is required by adding more methylene linkage (-CH 2 -) to establish this fact. Many oxadiazole analogues were reported as tubulin inhibitor.…”

Section: Anticancer Activitymentioning

confidence: 99%

“…[20] In the present investigation the heterocyclic (oxadiazole) linked aryl core of IMC-038525 (tubulin polymerization inhibitor), NSC 784595 and NSC 784597 was taken and two new series of oxadiazoles (4a-e and 4f-j) were synthesized. [21,22] The design of the title compounds (4a-e and 4f-j) is shown in Figure 1. The second series of oxadiazoles (4f-j) was designed with the incorporation of methylene linker with a hope to increase the pharmacological profile.…”

Section: Introductionmentioning

confidence: 99%

“…[23] The therapeutic potentials of incorporated methylene linker (-CH 2 -) is also reported elsewhere. [22,23] Results and discussion Chemistry The title compounds (4a-j) were synthesized as per the synthetic protocol outlined Scheme 1 and Scheme 2. The oxadiazole analogues of the series (4a-e) were synthesized starting from p-anisidine (1).…”

Section: Introductionmentioning

confidence: 99%

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Rationale Design, Synthesis And In Vitro Anticancer Activity of New 2,5‐Disubstituted‐1,3,4‐Oxadiazole Analogues

Ahsan¹

2016

ChemistrySelect

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Two new series of oxadiazole analogues (4a–e and 4f–j) were designed based on heterocyclic (1,3,4‐oxadiazole) linked aryl core of IMC‐038525 (tubulin polymerization inhibitor), NSC 784595, and NSC 784597. All the synthesized compounds were synthesized and characterized by IR, NMR, and mass spectral data and the purity of compounds was checked by elemental analysis. Eight compounds were evaluated for their in vitro anticancer activity on 9 different panels of 60 cell lines (60 NCI cancer cell lines) according to the National Cancer Institute (NCI) screening protocol and percent growth (GP) and percent growth inhibition (% GI) was calculated at 10 μM drug concentration. N‐{[5‐(4‐Chlorophenyl)‐1,3,4‐oxadiazol‐2‐yl]methyl}‐4‐methoxyaniline (4 g) showed maximum anticancer activity at 10 μM, and showed maximum sensitivity towards SNB‐75, MDA‐MB‐231/ATCC, T‐47D, 786–0, MCF7, EKVX, PC‐3, HS 578T, MOLT‐4, HCT‐116, HCT‐15, SR, COLO‐205, A549/ATCC, SF‐295, SNB‐19 and RPMI‐8226 with % GIs of 65.48, 60.21, 56.38, 50.36, 49.15, 47.36, 45.16, 41.37, 41.20, 40.02, 38.67, 37.39, 36.61, 34.64, 34.21, 33.77, and 32.92 respectively. Furthermore the compound 4 g showed superior anticancer activity than that of the standard drug Imatinib on 50 human cancer cell lines. The oxadiazoles containing methylene (‐CH2‐) linkage showed comparatively higher anticancer activity.

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Section: Anticancer Activitymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Rationale Design, Synthesis And In Vitro Anticancer Activity of New 2,5‐Disubstituted‐1,3,4‐Oxadiazole Analogues

Ahsan¹

2016

ChemistrySelect

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“…al. have designed, synthesized and screened 1,3,4‐oxadiazole‐linked aryl core (IV, Figure ) for various cancer cell lines . The novel analogs of benzosuberone (V, Figure ) embedded with 1,3,4‐oxadiazole / thiadiazole and 1,2,4‐triazole moieties were synthesized and explored for their anti‐proliferative activities by Yadagiri et al .…”

Section: Introductionmentioning

confidence: 99%

Design and Ultrasound Assisted Synthesis of Novel 1,3,4‐Oxadiazole Drugs for Anti‐Cancer Activity

2020

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An ultrasound assisted multi‐component synthesis of a series of 2‐(N‐heterocycle) substituted 1,3,4‐oxadiazoles have been performed. A proper IR, UV, Mass and NMR spectral analysis supported the 12 synthesized novel compounds. Compound 5‐bromo‐1‐((4‐chlorophenyl)((5‐(4‐hydroxyphenyl)‐1,3,4‐oxadiazol‐2‐yl)amino)methyl) indoline‐2,3‐dione (D8), displayed significant cytotoxicity against all the three human cancer cell lines studied in this article (breast cancer cell line MCF‐7, colorectal cancer cell line HT‐29 and liver cancer cell line Hep G2) using MTT assay. Further in silico target hunting using Chem Mapper led to the identification of two important cancer targets; EGFR and CDK2 kinases. Compound D8 was studied in detail using AutoDock and displayed high binding energies with the two proteins. Quantum chemical calculations of the designed compound D8 at the active site with specific amino acids for both the proteins showed stronger interactions at the active sites similar to the docking studies.

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“…Synthesis of such heterocyclic compounds are pharmaceutical important and a foremost task of chemists due to its vast pharmacological and industrial applications. A large number of heterocyclic systems with different hetero moieties act as good anticancer agents in cancer chemotherapy and showed potent anticancer activities against a panel of human cancer cell lines [1][2][3][4][5][6][7][8][9][10].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antitumor Evaluation of Novel 5-Bromo Indole-Aryl Keto Hydrazide-Hydrazone Analogues

Rudavath¹,

Sreenivasulu²,

Pinapati³

et al. 2018

Asian J. Chem.

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A wide variety of indole, substituted benzaldehyde linked keto hydrazide-hydrazone analogues were designed, synthesized and evaluated for their cytotoxicity against eight human cancer cell lines HeLa, A549, MCF-7, K562, HEK293, HT29, SF295 and HL60. All these synthesized compounds showed potent antitumor activities on the above eight human cancer cell lines. Among them, 6a and 6h compounds exhibited potent antitumor activity on HL 60 and A549 cancer cell lines with IC50 value of 3.913 and 4.838 µM than the standard drug cisplatin with IC50 values of 27 and 36 µM, respectively.

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Design and synthesis of new 2,5-disubstituted-1,3,4-oxadiazole analogues as anticancer agents

Cited by 59 publications

References 17 publications

Rationale Design, Synthesis And In Vitro Anticancer Activity of New 2,5‐Disubstituted‐1,3,4‐Oxadiazole Analogues

Rationale Design, Synthesis And In Vitro Anticancer Activity of New 2,5‐Disubstituted‐1,3,4‐Oxadiazole Analogues

Design and Ultrasound Assisted Synthesis of Novel 1,3,4‐Oxadiazole Drugs for Anti‐Cancer Activity

Synthesis and Antitumor Evaluation of Novel 5-Bromo Indole-Aryl Keto Hydrazide-Hydrazone Analogues

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