Synthesis, biological evaluation, and molecular docking studies of novel 1,3,4-oxadiazole derivatives possessing benzotriazole moiety as FAK inhibitors with anticancer activity

Zhang, Shuai; Luo, Yin; He, Liangqiang; Liu, Zhijun; Jiang, Aiqin; Yang, Yonghua; Zhu, Hai‐Liang

doi:10.1016/j.bmc.2013.04.043

Cited by 82 publications

(35 citation statements)

References 23 publications

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“…Focal adhesion kinase (FAK) is one of the most common intracellular kinases that regulate signalling pathways associated with cellular migration, proliferation, and survival [11], making it an important target in developing anticancer drugs. To produce better FAK inhibitors, Zhang and his team [12] designed and synthesised a series of new 1,3,4-oxadiazole derivatives possessing benzotriazole moiety ( Figure 3). Among the analogues, fluoro-substituted compound 6 displayed the best FAK inhibitory activity and performed better than the reference drug, cisplatin (Table 2).…”

Section: Fluoro (F) Groupmentioning

confidence: 99%

“…The FAK inhibitory effect of the 1,3,4-oxadiazole analogues was investigated [12]. The SAR analysis indicated that compounds with electron-donating groups showed weaker activity.…”

Section: Methyl (Ch 3 ) Groupsmentioning

confidence: 99%

“…All of the synthesised 1,3,4-oxadiazole analogues were examined for anticancer activity against MCF-7 and HT29 cell lines [12]. It was noticeable that the fluorinated compound 6 showed the best activity against MCF-7 cells with an IC 50 value of 5.68 µg/mL (Table 2) (Figure 25) [54].…”

Section: Fluoro (F) Groupmentioning

confidence: 99%

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A Review of the Structure–Activity Relationship of Natural and Synthetic Antimetastatic Compounds

et al. 2020

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There are innumerable anticancer compounds derived from either natural or synthetic origins. Many of these compounds have been further developed through structural modifications to not only inhibit cancer cell growth but also to exert an antimetastatic effect. This is achieved by attaching different substituents to generate different structure–activity relationships. This review highlights the effectiveness of different functional groups known to have antimigration and antiproliferation activities, such as fluoro, methoxy, methyl, amino, hydroxy, nitro, bromo, chloro, methylamino, ethoxy, carbonyl, iodo, and trifluoromethyl groups. Additionally, the positioning of these functional groups plays an important role in their anticancer activities, which was evident in one of our studies comparing analogues of a natural compound. Thus, this review suggests future recommendations for the design and development of improved anticancer drugs with higher efficacy.

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Section: Fluoro (F) Groupmentioning

confidence: 99%

“…The FAK inhibitory effect of the 1,3,4-oxadiazole analogues was investigated [12]. The SAR analysis indicated that compounds with electron-donating groups showed weaker activity.…”

Section: Methyl (Ch 3 ) Groupsmentioning

confidence: 99%

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A Review of the Structure–Activity Relationship of Natural and Synthetic Antimetastatic Compounds

et al. 2020

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“…Cancer cells can attack the neighboring undamaged parts of the body and spread to affect other organs [1]. Cancer is a disease that threatens human lives and causes the second highest rate of death globally [2][3][4]. Although there is continuous progress in the development of cancer treatment, the challenge to develop successful anticancer agents remains [5].…”

Section: Introductionmentioning

confidence: 99%

High‐dimensional QSAR prediction of anticancer potency of imidazo[4,5‐b]pyridine derivatives using adjusted adaptive LASSO

Algamal

Lee

Al-Fakih

et al. 2015

Journal of Chemometrics

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In high-dimensional quantitative structure-activity relationship (QSAR) studies, identifying relevant molecular descriptors is a major goal. In this study, a proposed penalized method is used as a tool for molecular descriptors selection. The method, called adjusted adaptive least absolute shrinkage and selection operator (LASSO) (AALASSO), is employed to study the high-dimensional QSAR prediction of the anticancer potency of a series of imidazo[4,5-b]pyridine derivatives. This proposed penalized method can perform consistency selection and deal with grouping effects simultaneously. Compared with other commonly used penalized methods, such as LASSO and adaptive LASSO with different initial weights, the results show that AALASSO obtains the best predictive ability not only by consistency selection but also by encouraging grouping effects in selecting more correlated molecular descriptors. Hence, we conclude that AALASSO is a reliable penalized method in the field of high-dimensional QSAR studies.

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“…These derivative compounds have been found to exhibit diverse biological activities such as analgesic, 1,2 anti-inflammatory, 1,2 antimicrobial, [2][3][4] anti-HIV, 5 antimalarial, 6,7 antifungicidal, 8,9 and other biological properties. [10][11][12][13][14] Some 1,3,4-oxadiazole derivatives have also been applied in the fields of photosensitizers, 15 liquid crystals 16,17 and organic light-emitting diodes (OLED). 18,19 Consequently, the synthesis of compounds containing this heterocyclic core has attracted considerable attention, and a wide variety of methods has been used for their assembly.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 1,3,4-oxadiazole derivatives from α-amino acid and acyl hydrazides under thermal heating or microwave irradiation conditions

Dornelles¹,

Rodrigues²,

Heck³

et al. 2015

Arkivoc

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Synthesis, biological evaluation, and molecular docking studies of novel 1,3,4-oxadiazole derivatives possessing benzotriazole moiety as FAK inhibitors with anticancer activity

Cited by 82 publications

References 23 publications

A Review of the Structure–Activity Relationship of Natural and Synthetic Antimetastatic Compounds

A Review of the Structure–Activity Relationship of Natural and Synthetic Antimetastatic Compounds

High‐dimensional QSAR prediction of anticancer potency of imidazo[4,5‐b]pyridine derivatives using adjusted adaptive LASSO

Synthesis of 1,3,4-oxadiazole derivatives from α-amino acid and acyl hydrazides under thermal heating or microwave irradiation conditions

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