Synthesis and antimicrobial activity of novel derivatives of Biginelli pyrimidines

Sedaghati, Bita; Fassihi, Afshin; Arbabi, Shirin; Ranjbar, Maryam; Memarian, Hamid Reza; Saghaie, Lotfollah; Omidi, Adel; Sardari, Alireza; Jalali, Mohammad; Abedi, Daryoush

doi:10.1007/s00044-011-9931-7

Cited by 28 publications

(11 citation statements)

References 16 publications

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“…Of note was the observation that the antimicrobial THPMs investigated in this research were stronger antifungals rather antibacterial agents. For example, 62a and 62b, which are shown in Figure 68, inhibited the fungal growth at lower concentrations (130). Figure 69.…”

Section: Antimicrobial Activitymentioning

confidence: 96%

Hantzsch-Type Dihydropyridines and Biginelli-Type Tetra-hydropyrimidines: A Review of their Chemotherapeutic Activities

Sepehri¹,

Sánchez²,

Fassihi³

2015

J Pharm Pharm Sci

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Years after the first report on 1,4-dihydropyridines (1,4-DHPs) and 1,2,3,4-tetrahydropyrimidines (1,2,3,4-THPMs) appeared, they are revisited as plausible therapeutic agents. This is mainly due to the convenient methods that exist for their synthesis and the diverse pharmacologic properties that these scaffolds present. 1,4-Dihydropyridines and 1,2,3,4-tetrahydropyrimidines are usually regarded as analogous in several aspects. They are both prepared in multi-component reactions using very similar starting materials and synthesis protocols. This leads to common structural features between 1,4-DHPs and 1,2,3,4-THPMs, as well several related biological effects. For example, they share many pharmacological features such as analgesic, anti-tumor, antioxidant, anti-inflammatory, antitubercular, antibacterial, cardiovascular and adrenoceptor blocking activities. Numerous reviews have been devoted to the chemistry and cardiovascular effects of these compounds. However, the lack of a comprehensive literature overview on the chemotherapeutic ability of these scaffolds is behind the present attempt to provide a detailed survey of 1,4-DHPs and 1,2,3,4-THPMs and their structural features as chemotherapeutic agents.This article is open to POST-PUBLICATION REVIEW. Registered readers (see “For Readers”) may comment by clicking on ABSTRACT on the issue’s contents page.

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Section: Antimicrobial Activitymentioning

confidence: 96%

Hantzsch-Type Dihydropyridines and Biginelli-Type Tetra-hydropyrimidines: A Review of their Chemotherapeutic Activities

Sepehri¹,

Sánchez²,

Fassihi³

2015

J Pharm Pharm Sci

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“…The synthesis and polymorphism property of methyl 4‐(4‐chlorophenyl)‐8‐iodo‐2‐methyl‐6‐oxo‐1,6‐dihydro‐4 H ‐pyrimido[2,1‐ b ]quinazoline‐3‐carboxylate has been the focus of our continuing interest because the presence of pharmacophore pyrimido[2,1‐ b ]quinazoline in the title compound is responsible for diverse pharmacological activities. For example, the substituted dihydropyrimidine ring system exhibited numerous pharmacological activities such as antibacterial , anticancer , antifungal , antihypertensive , antiinflammatory , and antitubercular properties . Some of the substituted dihydropyrimidine derivatives have been used as dipeptidyl peptidase‐IV (DPP‐4) inhibitors and non‐nucleoside HIV‐1 reverse transcriptase inhibitors .…”

mentioning

confidence: 99%

Synthesis, Polymorphism, and Insecticidal Activity of Methyl 4‐(4‐chlorophenyl)‐8‐iodo‐2‐methyl‐6‐oxo‐1,6‐dihydro‐4H‐pyrimido[2,1‐b]quinazoline‐3‐Carboxylate Against Anopheles arabiensis Mosquito

et al. 2016

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Mosquitoes are the major vectors of pathogens and parasites including those causing malaria, the most deadly vector-borne disease. The negative environmental effects of most synthetic compounds combined with widespread development of insecticide resistance encourage an interest in finding and developing alternative products against mosquitoes. In this study, pyrimido[2,1-b]quinazoline derivative DHPM3 has been synthesized by three-step chemical reaction and screened for larvicide, adulticide, and repellent properties against Anopheles arabiensis, one of the dominant vectors of malaria in Africa. The title compound emerged as potential larvicide agent for further research and development, because it exerted 100% mortality, while adulticide activity was considered moderate.

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“…Also known as Biginelli adducts, 3,4-Dihydropyrimidinones (DHPMs), are compounds derived from pyrimidine, in which carbon C-4 is entirely saturated, eliminating the characteristic aromaticity of a pyrimidine; a double bond is formed on the C-5 and a second one towards a heteroatom, on carbon C-2. The synthesis of DHPMs (dihydropyrimidines) has become a line of research due to the importance of the antihypertensive [1,2], antibacterial [3,4], antifungal [5,6], antiviral [7], anti-inflammatory, and antineoplastic activity [8,9] they show, through various mechanisms such as calcium channels, GABA agonists, and α1A-adrenergic antagonists [10,11]. Such derivatives can quickly be obtained through the Biginelli reaction, developed in 1893 by Pietro Biginelli [12].…”

Section: Introductionmentioning

confidence: 99%

Understanding the Lack of Reactivity of 2,4-Dihydroxybenzaldehyde Towards the Biginelli Adduct Using Density Functional Theory Molecular Modeling

et al. 2019

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The Biginelli reaction is a multicomponent reaction for obtaining dihydropyrimidinthiones quickly, with multiple substitution patterns. The reaction mechanism remains unclear. Three possible pathways proposed for the reaction are the iminium route, an enamine intermediate, and the Knoevenagel pathway. However, when thiourea was used, no theoretical calculations were reported. Thus, based on the literature, the iminium pathway was used to obtain evidence explaining the lack of reactivity of 2,4-dihydroxybenzaldehyde towards the Biginelli adduct, compared with 4-hydroxybenzaldehyde. This computational study, carried out using the B3LYP/6-31++G(d,p) level of theory, showed an increment of 150 kJ/mol in the activation energy of the slowest pathway, due to the presence of a hydroxyl group in position 2 (ortho) of the aromatic aldehyde, decreasing its reactivity. Natural bond orbital (NBO) calculations suggest that the determinant steps are simultaneous, i.e., the polarization of the carbonyl group and its corresponding protonation by the hydrogen of the SH fragment of the thiourea tautomer. The activation enthalpy values suggest that the nucleophile attack takes place later on the compound 2,4-dihydroxybenzaldehyde compared to 4-hydroxybenzaldehyde-TS, confirming that the OH group in position 2 hinders the condensation reaction.

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Synthesis and antimicrobial activity of novel derivatives of Biginelli pyrimidines

Cited by 28 publications

References 16 publications

Hantzsch-Type Dihydropyridines and Biginelli-Type Tetra-hydropyrimidines: A Review of their Chemotherapeutic Activities

Hantzsch-Type Dihydropyridines and Biginelli-Type Tetra-hydropyrimidines: A Review of their Chemotherapeutic Activities

Synthesis, Polymorphism, and Insecticidal Activity of Methyl 4‐(4‐chlorophenyl)‐8‐iodo‐2‐methyl‐6‐oxo‐1,6‐dihydro‐4H‐pyrimido[2,1‐b]quinazoline‐3‐Carboxylate Against Anopheles arabiensis Mosquito

Understanding the Lack of Reactivity of 2,4-Dihydroxybenzaldehyde Towards the Biginelli Adduct Using Density Functional Theory Molecular Modeling

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