Synthesis and initial biological evaluation of substituted 1-phenylamino-2-thio-4,5-dimethyl-1H-imidazole derivatives

Yurttaş, Leyla; Duran, Murat; Demirayak, Şeref; Gençer, Hülya Karaca; Tunalı, Yağmur

doi:10.1016/j.bmcl.2013.10.024

Cited by 37 publications

(20 citation statements)

References 15 publications

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“…Motivated by this result, we aimed to develop a one-pot sequential multicomponent reaction (MCR) [18] as alternative method for regioselective synthesis of a new series of imidazole-2-thiones-containing structure as suitable precursor for drug-like compounds [19].…”

Section: Methodsmentioning

confidence: 99%

Sequential MCR via Staudinger/aza-Wittig versus Cycloaddition Reaction to Access Diversely Functionalized 1-amino-1H-imidazole-2(3H)-thiones

Ciccolini¹,

Mari²,

Favi³

et al. 2019

Preprint

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A Multicomponent Reaction (MCR) strategy, alternative to the known cycloaddition reaction, towards variously substituted 1-amino-1H-imidazole-2(3H)-thione derivatives has been successfully developed. The novel approach involves α-halohydrazones whose azidation process followed by tandem Staudinger/aza-Wittig reaction with CS2 in a sequential MCR regioselectively leads to the target compounds avoiding the formation of the regioisomer iminothiazoline heterocycle. The approach can be applied to a range of differently substituted α-halohydrazones bearing also electron-withdrawing groups confirming the wide scope and the substituent tolerance of the process for the synthesis of the target compounds. Interestingly, the concurrent presence of reactive functionalities in the scaffolds so obtained, ensures postmodifications in view of N-bridgedheaded heterobicyclic structures.

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Section: Methodsmentioning

confidence: 99%

Sequential MCR via Staudinger/aza-Wittig versus Cycloaddition Reaction to Access Diversely Functionalized 1-amino-1H-imidazole-2(3H)-thiones

Ciccolini¹,

Mari²,

Favi³

et al. 2019

Preprint

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“…Maximum derivatives were found active against different cancerous cell lines (Chen et al, 2013a). Some derivatives of 2-[(4,5-dimethyl-1-(arylamino)-1H-imidazol-2-yl)thio]-1-(aryl)ethanone were synthesized and evaluated them for anti-cancerous activities by brine shrimp lethality assay and found active (Yurttaş et al, 2013). Copper complex of imidazole with taurine Schiff base was synthesized and tested for its cytotoxic analysis.…”

Section: Anti-cancermentioning

confidence: 99%

Imidazole and its derivatives as potential candidates for drug development

Mumtaz

Saeed

Fatima

et al. 2016

Bangladesh J Pharmacol

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Imidazole and its derivatives are the pharmacological significant scaffolds with the broad spectrum of activities can be synthesized in the laboratory in the single step by the action of the catalyst. The current review summarizes the role of the imidazole and its derivatives during the last decade (2005)(2006)(2007)(2008)(2009)(2010)(2011)(2012)(2013)(2014) for the treatment of many diseases. Review highlights their significant contribution towards the drug development for the treatment of some fatal diseases like HIV, cancer, tuberculosis and hepatitis C. As imidazole and its derivatives continue to play an important role for the treatment of many diseases so there is a need to trigger research in this field. Article InfoReceived:26 Mini-reviewThis article was downloaded by you on: Oct 01, 2016 2009), anti-oxidant (Sorrenti et al., 2006) and antidepressant (Dostert et al., 1990) are the known examples.Synthesis of imidazole ring and its derivatives is carried out by using one-step condensation of diketone with aldehyde, ammonium acetate and primary aromatic amine in the presence of nanocrystalline magnesium aluminate (Safari et al., 2013), supported ionic liquidlike phase (Saffari Jourshari et al., 2013), SiO2-Pr-SO3H (Ziarani et al., 2013, clay supported titanium catalyst (Kannan and Sreekumar, 2013), brønsted acidic ionic liquid,(4-sulfobutyl)tris(4-sulfophenyl)phosphonium hydrogen sulfate (Banothu et al., 2013), nano-TiCl4.SiO2 (Mirjalili et al., 2012) I2/Cs2CO3 (Xue et al., 2014 and sulfonic acid functionalized SBA-15 nanoporous material (SBA-Pr-SO3H) catalyst .As imidazole and its derivatives are associated with a number of biological significances so the current review will emphasized on the role of imidazole and its derivative as potential candidate for the development of drugs to treat some fatal diseases including HIV-AIDS (de Walque, 2014), cancer (Fraser et al., 2014), hepatitis-C (Linas et al., 2014) and tuberculosis (Zoraghi and Reiner, 2013), etc. Pharmacological SignificancesFrom the literature, it is found that imidazole and their derivatives they possess potent activities against fetal diseases and playing a significant role in a fight against them. Anti-HIV activityAcquired immunodeficiency syndrome (AIDS) is a viral disease caused due to the special virus Human Immunodeficiency Virus type 1 (HIV-1) (Basu et al., 2009). The HIV-1 type virus destroys the lymphocytes the 'helper cell' which fight against the infections (Roy and Leonard, 2005). According to World Health Organization report, three million people were suffering from AIDS and more than five million people acquire the AIDS in the single year (AIDS, 2003). As the HIV-AIDS is increasing globally and there is a need to introduce some new drugs to help in a fight against this fatal disease. In this regard imidazole and their derivatives are playing a significant role in the treatment of disease. During the course of drugs for the treatment of HIV-AIDS, the activity is mainly focused on the interaction of the compound with t...

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“…[1][2][3][4] The imidazole derivatives with different biological activities, including antimicrobial, [5] anticonvulsant, [6] anticancer, [7,8] and antiviral, [9] are present in the literature. Also, many of today's drugs include imidazole skeleton in their structure such as Clonidine (a 2 adrenergicagonist), Idazoxan, and Napamazole (antidepressant) [3,10,11] (Fig.…”

Section: Introductionmentioning

confidence: 99%

Efficient Microwave-Assisted Synthesis of N-(2-Alkyl/aryl-4-phenyl-1H-imidazol-1-yl)-2-phenylacetamides

Menteşe

Yılmaz

2014

Synthetic Communications

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An easy, efficient, and environmentally friendly method for the synthesis of N-(2-alkyl/aryl-4-phenyl-1H-imidazol-1-yl)-2-phenylacetamides from the reaction of phenyl acylbromides and phenylacetohydrazide derivatives has been presented. Shorter reaction times, simple workup procedure, no catalyst requirement, and use of small quantities of organic solvent are the most obvious advantages of this protocol.

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Synthesis and initial biological evaluation of substituted 1-phenylamino-2-thio-4,5-dimethyl-1H-imidazole derivatives

Cited by 37 publications

References 15 publications

Sequential MCR via Staudinger/aza-Wittig versus Cycloaddition Reaction to Access Diversely Functionalized 1-amino-1H-imidazole-2(3H)-thiones

Sequential MCR via Staudinger/aza-Wittig versus Cycloaddition Reaction to Access Diversely Functionalized 1-amino-1H-imidazole-2(3H)-thiones

Imidazole and its derivatives as potential candidates for drug development

Efficient Microwave-Assisted Synthesis of N-(2-Alkyl/aryl-4-phenyl-1H-imidazol-1-yl)-2-phenylacetamides

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