Ultrasound Mediated One-Pot, Three Component Synthesis, Docking and ADME Prediction of Novel 5-Amino-2-(4-chlorophenyl)-7-Substituted Phenyl-8,8a-dihydro-7H-(1,3,4)thiadiazolo(3,2-α)pyrimidine-6-carbonitrile Derivatives as Anticancer Agents

Tiwari, Shailee V.; Seijas, Julio A.; Vázquez-Tato, M. Pilar; Sarkate, Aniket P.; Lokwani, Deepak K.; Nikalje, Anna Pratima

doi:10.3390/molecules21080894

Cited by 42 publications

(30 citation statements)

References 25 publications

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“…In this context, tetronic acid type 27 was used as the 1,3-dicarbonyl parent in a straightforward construction of the 4-aza-podophyllotoxin skeleton embedded with a thiazole unit [145]. Thus, tetronic acid (27) Alternatively, an eco-friendly access to thiadiazolo[3,2-a]pyrimidine-6-carbonitriles from a 1,3,4-thiadiazol-2-amine was reported in 2016 [148].…”

Section: Thiazole Derivativesmentioning

confidence: 99%

Synthesis of Biologically Active Molecules through Multicomponent Reactions

et al. 2020

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Focusing on the literature progress since 2002, the present review explores the highly significant role that multicomponent reactions (MCRs) have played as a very important tool for expedite synthesis of a vast number of organic molecules, but also, highlights the fact that many of such molecules are biologically active or at least have been submitted to any biological screen. The selected papers covered in this review must meet two mandatory requirements: (1) the reported products should be obtained via a multicomponent reaction; (2) the reported products should be biologically actives or at least tested for any biological property. Given the diversity of synthetic approaches utilized in MCRs, the highly diverse nature of the biological activities evaluated for the synthesized compounds, and considering their huge structural variability, much of the reported data are organized into concise schemes and tables to facilitate comparison, and to underscore the key points of this review.Molecules 2020, 25, 505 2 of 71 acetylcholinesterase inhibitors, anti-HIV, antimicrobial, antioxidant, anti-mycobacterial and anticancer activities ( Figure 1). It is noteworthy that 64% and 16% of the supporting literature found for this review correspond to heterocyclic structures with anticancer and antimicrobial activities, respectively. Scheme 2. Three-component synthesis of 3,4-dihydropyrimidinones/thiones type 7 under microwave irradiation, for anti-inflammatory activity.Patil et al., reported a one-pot pseudo-five-component synthesis of highly functionalized tetrahydropyridines 9 using Cu(OTf) 2 as catalyst, Scheme 3. In vitro anti-inflammatory activity of the obtained compounds 9 was determined against matrix metalloproteinases (MMPs) as MMP-2 and MMP-9 by using gelatin zymography [29]. Scheme 3. Multicomponent Cu(OTf) 2 catalyzed synthesis of substituted tetrahydropyridines 9 for anti-inflammatory activity.A highly diastereoselective synthesis (exclusively the cis isomer is formed), of chromeno β-lactam hybrids 13/14 was also achieved by an efficient one-pot three-component reaction between either 5,5-dimethylcyclohexane-1,3-dione (10a) or 4-hydroxycoumarin (10b), diverse benzaldehydes 11 and malononitrile (12), in the presence of DABCO under reflux conditions (Scheme 4). Scheme 4. Three-component synthesis of β-lactam hybrids 13/14 for anti-inflammatory activity.The synthesized compounds (13 in 80-95% yield) and (14 in 82-95% yield) were screened for anti-inflammatory activity (as well as for anticancer activity, please see Section 3.13.13. Compound 13b (Ar = 4-ClC 6 H 4 , Ar 1 = 4-MeC 6 H 4 ) was the most active of all the chromeno β-lactam hybrids 13/14 tested, with a 19.8 anti-inflammatory ratio, although, it resulted less active than the reference drug dexamethasone corticosteroid used for the treatment of rheumatoid and skin inflammation [30].

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Section: Thiazole Derivativesmentioning

confidence: 99%

Synthesis of Biologically Active Molecules through Multicomponent Reactions

et al. 2020

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“…In continuation of our work [20][21][22][23][24][25][26][27][28][29] here, we desire to state the advancement and execution of a methodology allowing for the synthesis of some new (Z)-5-(substituted benzylidene)-2-((substituted phenyl) amino)thiazol-4(5H)-one analogues. We have reported reaction under conventional method, which proceeds in short reaction time and give good to excellent yield.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of (Z)-5-(substituted benzylidene)-2-((substituted phenyl) amino)thiazol-4(5H)-one analogues with antitubercular activity

Shelke

Pansare

Sarkate

et al. 2019

Journal of Taibah University for Science

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We initiated a program to synthesize thiazolidinone derivatives as antitubercular agent by preparing hybrid molecules having the similar features of reported potent antitubercular agents. We desire to state the advancement and execution of a methodology allowing for the synthesis of some new (Z)-5-(substituted benzylidene)-2-((substituted phenyl) amino)thiazol-4(5H)-one analogues with antitubercular activity. A highly efficient protocol was developed for the synthesis with excellent yields as well as evaluated in vitro for their antimycobacterial activity against Mycobacterium tuberculosis MTB H37Ra and M. bovis BCG strains. Among these synthesized compounds 6a, 6c, 6e, 6f and 6i showed marginal antitubercular activity in the series along with no significant cytotoxicity against the MCF-7 and A549 human cancer cell lines. ARTICLE HISTORY

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“…In continuation of our work , on the synthesis of bioactive compounds, we have synthesized some 1,3,4‐oxadiazole analogues. The synthetic protocols employed for the synthesis of oxadiazole derivatives 3 and 4 are presented in Schemes , , and , respectively.…”

Section: Introductionmentioning

confidence: 99%

A Facile Synthesis of Substituted 2‐(5‐(Benzylthio)‐1,3,4‐oxadiazol‐2‐yl)pyrazine Using Microwave Irradiation and Conventional Method with Antioxidant and Anticancer Activities

Patil

Sarkate

Karnik

et al. 2019

Journal of Heterocyclic Chem

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A series of novel substituted 2‐(5‐(benzylthio)‐1,3,4‐oxadiazol‐2‐yl)pyrazine derivatives (6a–n) were synthesized under microwave irradiation and conventional conditions with less reaction time with good to excellent yields. All the synthesized compounds were screened for antioxidant and anticancer activities. Out of the 14 prepared derivatives, compounds 6f and 6m were most potent and active with antioxidant and anticancer activities, respectively. Also, the developed technique was simple, easy, and less time consuming.

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Ultrasound Mediated One-Pot, Three Component Synthesis, Docking and ADME Prediction of Novel 5-Amino-2-(4-chlorophenyl)-7-Substituted Phenyl-8,8a-dihydro-7H-(1,3,4)thiadiazolo(3,2-α)pyrimidine-6-carbonitrile Derivatives as Anticancer Agents

Cited by 42 publications

References 25 publications

Synthesis of Biologically Active Molecules through Multicomponent Reactions

Synthesis of Biologically Active Molecules through Multicomponent Reactions

Synthesis of (Z)-5-(substituted benzylidene)-2-((substituted phenyl) amino)thiazol-4(5H)-one analogues with antitubercular activity

A Facile Synthesis of Substituted 2‐(5‐(Benzylthio)‐1,3,4‐oxadiazol‐2‐yl)pyrazine Using Microwave Irradiation and Conventional Method with Antioxidant and Anticancer Activities

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