Synthesis and biological evaluation of 2-amino-1-thiazolyl imidazoles as orally active anticancer agents

Li, Wen Tai; Hwang, Der Ren; Song, Jen Shin; Chen, Ching Ping; Chen, Tung Wei; Lin, Chi; Chuu, Jiunn Jye; Lien, Tzu-Wen; Hsu, Tsu; Huang, Chen; Tseng, Huan Yi; Lin, Chu Chung; Lin, Heng Liang; Chang, Chung Ming; Chao, Yu Sheng; Chen, Chiung Tong

doi:10.1007/s10637-010-9547-7

Cited by 10 publications

(4 citation statements)

References 39 publications

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“…In another work, a group of imidazoles linked with a thiazole moiety were promoted as orally active microtubule destabilizing anticancer agents. 148 The reported imidazoles were evaluated for cytotoxic activity against the human gastric cancer NUGC-3 cells. Among the group, compound 22 (1-(4-phenylthiazol-2-yl)-4-(thiophen-2-yl)-1H-imidazol-2-amine) with an IC 50 value of 0.05 μM was found to be potent against human cancer cells.…”

Section: Imidazoles As Microtubule Destabilizing Anticancer Agentsmentioning

confidence: 99%

Imidazoles as potential anticancer agents

2017

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Cancer is a black spot on the face of humanity in this era of science and technology. Presently, several classes of anticancer drugs are available in the market, but issues such as toxicity, low efficacy and solubility have decreased the overall therapeutic indices. Thus, the search for new promising anticancer agents continues, and the battle against cancer is far from over. Imidazole is an aromatic diazole and alkaloid with anticancer properties. There is considerable interest among scientists in developing imidazoles as safe alternatives to anticancer chemotherapy. The present article describes the structural, chemical, and biological features of imidazoles. Several classes of imidazoles as anticancer agents based on their mode of action have been critically discussed. A careful observation has been made into pharmacologically active imidazoles with better or equal therapeutic effects compared to well-known imidazole-based anticancer drugs, which are available on the market. A brief discussion of the toxicities of imidazoles has been made. Finally, the current challenges and future perspectives of imidazole based anticancer drug development are conferred.

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Section: Imidazoles As Microtubule Destabilizing Anticancer Agentsmentioning

confidence: 99%

Imidazoles as potential anticancer agents

2017

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“…Moreover, this compound could distribute efficiently to the tumor tissues at effective concentrations and significantly prolong the lifespan of the leukemia mice. Contrast tests revealed that the replacement of thiophene and phenyl groups by other fragments would decrease the anticancer potency . These amino imidazole‐based tubulin‐targeting compounds are worthy to be further investigated as potential candidates for cancer chemotherapy.…”

Section: Imidazoles As Anticancer Agentsmentioning

confidence: 99%

Comprehensive Review in Current Developments of Imidazole-Based Medicinal Chemistry

et al. 2013

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Imidazole ring is an important five-membered aromatic heterocycle widely present in natural products and synthetic molecules. The unique structural feature of imidazole ring with desirable electron-rich characteristic is beneficial for imidazole derivatives to readily bind with a variety of enzymes and receptors in biological systems through diverse weak interactions, thereby exhibiting broad bioactivities. The related research and developments of imidazole-based medicinal chemistry have become a rapidly developing and increasingly active topic. Particularly, numerous imidazole-based compounds as clinical drugs have been extensively used in the clinic to treat various types of diseases with high therapeutic potency, which have shown the enormous development value. This work systematically gives a comprehensive review in current developments of imidazole-based compounds in the whole range of medicinal chemistry as anticancer, antifungal, antibacterial, antitubercular, anti-inflammatory, antineuropathic, antihypertensive, antihistaminic, antiparasitic, antiobesity, antiviral, and other medicinal agents, together with their potential applications in diagnostics and pathology. It is hoped that this review will be helpful for new thoughts in the quest for rational designs of more active and less toxic imidazole-based medicinal drugs, as well as more effective diagnostic agents and pathologic probes.

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“…The dacarbazine, an anticancer agent containing imidazole nucleus are used in the treatment of various cancers such as sarcoma, metastatic malignant melanoma, neuroblastoma, islet cell carcinoma, Hodgkin lymphoma, carcinoma of the pancreas and medullary carcinoma of thyroid [35] . Some other examples of marketed drugs used in cancer‐containing imidazole scaffold including nocodazole, bendamustine, veliparib, glasdegib, abemaciclib, liarozole, crenolanib, pracinostat, tipifarnib have been shown in Figure 3 [36] …”

Section: Introductionmentioning

confidence: 99%

Hybridization of Imidazole with Various Heterocycles in Targeting Cancer: A Decade's Work

Teli¹,

Chawla²

2021

ChemistrySelect

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Cancer is the world‘s biggest global health concern. The prevalence and mortality rates of cancer remain high despite significant progress in cancer therapy. The search for more effective, as well as less toxic treatment methods for cancer, is at the focus of current studies. Approximately 24.6 million people are suffering from cancer across the world as per the world health organization (WHO). In the year 2020, approximately 10 million deaths were reported due to cancer which has emerged as the second leading cause of mortality across the globe. Anticancer medicines have played a pivotal role in the medication of different types of cancers; however, they are associated with several side effects and relevance of drug resistance which evoke an immediate need for designing of new anticancer agents with multitargeted effect. Imidazole is a heterocyclic compound privileged with considerable anticancer activities and some imidazole derivatives have already got approval to treat cancer. Many hybrid molecules are available that play an important role in the treatment of cancer like chalcone, pyrazole, purine, triazine etc., and their pharmacophore provide the anticancer drug with low drug resistance and high efficacy, with low chances of toxicity and side effects. This review provides various approaches for the drug development of new safe and efficient antitumor agents imidazole hybrids with other heterocyclic moieties. An attempt has been made to advancement of the anticancer potential of the derivatives and hybrids of imidazole having intact or condensed imidazole moiety in the last decade along with the structure‐activity relationship studies, and mechanism of action.

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Synthesis and biological evaluation of 2-amino-1-thiazolyl imidazoles as orally active anticancer agents

Cited by 10 publications

References 39 publications

Imidazoles as potential anticancer agents

Imidazoles as potential anticancer agents

Comprehensive Review in Current Developments of Imidazole-Based Medicinal Chemistry

Hybridization of Imidazole with Various Heterocycles in Targeting Cancer: A Decade's Work

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