Design and Rapid Microwave Irradiated One-Pot Synthesis of Tetrahydropyrimidine Derivatives and Their Screening <i>In Vitro</i> Antidiabetic Activity

Lalpara, Jaydeep N.; Hadiyal, Sanjay D.; Radia, Ashish J.; Dhalani, J. M.; Dubal, G. G.

doi:10.1080/10406638.2020.1852586

Cited by 16 publications

(14 citation statements)

References 16 publications

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“…Compounds 4d , 4g , 4i , 4j , 5b and 5f that exhibited IC 50 values (lg mL −1 ) in good ranges; 71.46, 72.41, 72.27, 70.62, 72.79, and 72.10 respectively that nearer to 69.71 for acarbose. 222 Aminopyrimidines ( 21–40 ) were showed a good percentage of inhibition for α-glycosidase (13–72%) and glycogen phosphorylase (10–40%) and by excluding 31 , 34 , 35 , and 37 had moderate to good inhibitory potential. SAR study of the compounds revealed that phenyl ring substitution in arylidene showed good inhibition of glycosidase enzyme, i.e.…”

Section: Synthetic Agents As Antidiabeticsmentioning

confidence: 98%

“…Compounds 4d, 4g, 4i, 4j, 5b and 5f that exhibited IC 50 values (lg mL À1 ) in good ranges; 71.46, 72.41, 72.27, 70.62, 72.79, and 72.10 respectively that nearer to 69.71 for acarbose. 222 Aminopyrimidines (21)(22)(23)(24)(25)(26)(27)(28)(29)(30)(31)(32)(33)(34)(35)(36)(37)(38)(39)(40) were showed a good percentage of inhibition for a-glycosidase (13-72%) and glycogen phosphorylase (10-40%) and by excluding 31, 34, 35, and 37 had moderate to good inhibitory potential. SAR study of the compounds revealed that phenyl ring substitution in arylidene showed good inhibition of glycosidase enzyme, i.e., compounds 24, 25, 29 and 36 with p-bromo (71.8%), p-chloro (72.8%), p-benzyloxy (53.1%), and p-methoxy (63.2%), respectively, against a-glycosidase but also found more effective against glycogen phosphorylase.…”

Section: Antidiabetic Activities Of Pyrimidinesmentioning

confidence: 99%

“…The reaction of oxadiazole contains aldehyde moiety with substituted acetoacetanilide and urea derivatives in acidic ethanol under microwave irradiation (200 W) up to 25 min. 222 The reaction of various bis-benzylidene cycloheptanones and bis-benzylidene cyclohexanones with guanidine hydrochloride was conducted in the presence of NaH and DMF as a solvent to obtain the amino pyrimidine in moderate to good yields. 223 Negoro and coworkers reported the synthesis of morpholino pyrimidine derivatives.…”

Section: Synthetic Agents As Antidiabeticsmentioning

confidence: 99%

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Heterocyclic compounds as a magic bullet for diabetes mellitus: a review

Farwa

Raza

2022

RSC Adv.

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Section: Synthetic Agents As Antidiabeticsmentioning

confidence: 98%

Section: Antidiabetic Activities Of Pyrimidinesmentioning

confidence: 99%

Section: Synthetic Agents As Antidiabeticsmentioning

confidence: 99%

See 1 more Smart Citation

Heterocyclic compounds as a magic bullet for diabetes mellitus: a review

Farwa

Raza

2022

RSC Adv.

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“…Currently, much consideration has been paid to pyrimidine derivatives due to their biological activity and therapeutical potential. [3] Tetrahydropyrimidine (THPM) derivatives shows a wide range of biological activities such as anticancer [4] , antimicrobial [5] , anti-inflammatory [6] , antimalarial [7] , and anti-diabetic [8] activities. Pyrimidine-2-thione moiety inhibits the motility of the mitotic kinesin Eg5.…”

Section: Introductionmentioning

confidence: 99%

Microwave-assisted synthesis of bioactive tetrahydropyrimidine derivatives as antidiabetic agents

Vachhani¹,

Lalpara²,

Hadiyal³

et al. 2022

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Introduction: In drug discovery, pyrimidine analogues show good biological response and many drug moieties have pyrimidine core. Aim: On the basis of prior review, we synthesized a series of N-(substituted phenyl)-1,3,6-trimethyl-4-(4-((5-(4-nitrophenyl)-1,3,4-oxadiazol-2-yl)methoxy)phenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide parade a 1,3,4-oxadiazole core which were evaluated for in vitro antidiabetic screening. Materials and methods: The tetrahydropyrimidine derivatives have been synthesized by microwave irradiation method. It was carried out by Biginelli condensation of 1,3,4-oxadiazole based aldehyde, substituted acetoacetanilide and N,N’-dimethyl urea. All synthesized compounds were evaluated for antidiabetic screening. Results: By the results derived from antidiabetic activity, compounds 4a, 4e, 4g, and 4i show good inhibition compared to others because of electron withdrawing and hydroxyl groups. All results are compared with standard drug acarbose. Conclusions: In conclusion, a series of 1,3,4-oxadizole bearing tetrahydropyrimidine has been synthesized and evaluated for in vitro antidiabetic screening. The derivatives 4a, 4e, 4g, and 4i exhibited promising antidiabetic activity.

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“…Out of which one of moiety is tetrahydropyridopyrazine (TPP) subunits. Nitrogen containing scaffolds were used as antitubercular (TB) [1], anaplastic lymphoma kinease (ALK) inhibitor [2], antidiabetic [3], anticancer [4], and PARP inhibitor. Various analogs of pyridopyrazines were part of various peptidomimetic scaffolds [5].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of new tetrahydropyridopyrazine derivatives via continuous flow chemistry approach and their spectroscopic characterizations

Parmar

Hadiyal

Kapupara

et al. 2021

Journal of Heterocyclic Chem

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We report here the synthesis of different substituted tetrahydropyridopyrazine derivatives. This approach of synthesis has been designed in a way that in first simple chloro-amine coupling as an alternative of Buchwald coupling followed by heterogeneous hydrogenation of nitro to give amine and further cyclization of this amine with carboxylic acid was accomplished in a single process with the help of continuous flow hydrogenation reactor. This processing was a generation of hydrogen (in situ) by electrolysis of water molecule and using a prepacked cartridge of a palladium catalyst. In a further step, LAH was used to reduce lactam to a yielding product as tetrahydropyridopyrazine (TPP) scaffold. Final adducts were obtained using substituted benzoyl and sulfonyl derivatives.

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Design and Rapid Microwave Irradiated One-Pot Synthesis of Tetrahydropyrimidine Derivatives and Their Screening In Vitro Antidiabetic Activity

Cited by 16 publications

References 16 publications

Heterocyclic compounds as a magic bullet for diabetes mellitus: a review

Heterocyclic compounds as a magic bullet for diabetes mellitus: a review

Microwave-assisted synthesis of bioactive tetrahydropyrimidine derivatives as antidiabetic agents

Synthesis of new tetrahydropyridopyrazine derivatives via continuous flow chemistry approach and their spectroscopic characterizations

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