Research developments in the syntheses, anti-inflammatory activities and structure–activity relationships of pyrimidines

Rashid, Haroon Ur; Martines, Marco Antônio Utrera; Duarte, Adriana Pereira; Jorge, Juliana; Rasool, Shagufta; Muhammad, Raza; Ahmad, Nasir; Umar, Muhammad Naveed

doi:10.1039/d0ra10657g

Cited by 69 publications

(28 citation statements)

References 154 publications

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“…Pyrimidine-based and fused bicyclic-based COX-2 inhibitors have also been reported to have selective COX-2 inhibition. 38,48 Acyclic non-diaryl heterocyclic molecules are a new class of COX-2 inhibitors without a central heterocycle core. 38,49 Acyclic inhibitors have diverse backbones (e.g., olefin, acetylene, azo, imine, unsaturated ketones), which are substituted with di-and triaryl (or -alkyl) functions.…”

Section: Rsc Medicinal Chemistrymentioning

confidence: 99%

Non-steroidal anti-inflammatory drugs: recent advances in the use of synthetic COX-2 inhibitors

et al. 2022

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Section: Rsc Medicinal Chemistrymentioning

confidence: 99%

Non-steroidal anti-inflammatory drugs: recent advances in the use of synthetic COX-2 inhibitors

et al. 2022

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“…Its structure known as constituent of nature drugs: theophylline and caffeine; as well as synthetically marketing drugs: Broxuridine, Fluorouracil, Tetroxoprim, Piribedil, and Pyrantel Embonate [10,11] (Figure 1). On the other hand, pyrimidines have a wide variety of interesting biological activities such as: anticancer [12,13], antiviral [14], antibacterial [15], analgesic [16], antioxidant [17,18], and anti‐inflammatory activities [19].…”

Section: Introductionmentioning

confidence: 99%

Utility of [4‐(3‐methoxyphenyl)pyrimidin‐2‐yl]cyanamide in synthesis of some heterocyclic compounds

Hussein

Khodairy

2021

Journal of Heterocyclic Chem

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N‐[4‐(3‐Methoxyphenyl)pyrimidin‐2‐yl]cyanamide (1) was reacted with morpholine and respective binuclephilic reagents namely: ethylenediamine, o‐phenylenediamine, o‐aminothiophenol, or o‐aminophenol to give the corresponding carboximidamide 2, imidazolidine 3, and benzazoles 4–6. While its reaction with hydrazides in DMF at 90°C, gave the corresponding 1,2,4‐triazols 7–11. Also, treatment of cyanamide 1 with heterocycles having both nucleophilic and electrophilic groups (─NH2/─COOEt) in iso‐propanol in presence of catalytic amount of Conc. HCl, gave the corresponding thieno[2,3‐d]pyrimidinone 12 and unexpected thieno[3,2‐d]pyrimidine 13 instead of bis‐thieno[3,2‐d]pyrimidine 14, respectively. While, its reaction with ethyl 5‐amino‐1,3‐thiazole‐4‐carboxylate yielded the unexpected N‐(pyrimidin‐2‐yl)urea 15 rather than the corresponding thiazolo[5,4‐d]pyrimidine 16. Unexpected N‐(pyrimidin‐2‐yl)thiourea 17 was obtained, when cyanamide 1 reacted with potassium thiolates in iso‐propanol with catalytic amount of Conc. HCl.

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“…The pyrimidine ring is a well-known and established constituent of many synthetic drugs commonly used in medicine that demonstrate a variety of pharmacological activities, especially antimicrobial (e.g., trimethoprim, pyrimethamine, zidovudine, flucytosine) and antineoplastic (e.g., fluorouracil, gemcitabine, cytarabine) [1]. It is still among the leading compounds investigated by medicinal chemists for practical clinical applications of its derivatives [2]. It is also ubiquitous in nature due to the presence of nitrogenous bases in DNA and RNA.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Crystal Structure, and Biological Evaluation of Novel 5-Hydroxymethylpyrimidines

et al. 2021

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Pyrimidine displays a wide array of bioactivities, and thence, it is still considered a potent unit of new drug research. Its derivative, 5-hydroxymethylpyrimidine, can be found as a scaffold of nontypical nitrogen bases in DNA and as a core of some natural bioactive compounds. In this study, we obtained a series of 5-hydroxymethylpyrimidines that vary in the 4-position by the reduction of proper esters. All compounds were characterized by spectroscopic analysis, and single-crystal X-ray diffraction was performed for some of them. Biological investigations estimated cytotoxic properties against normal (RPTEC) and cancer (HeLa, HepaRG, Caco-2, AGS, A172) cell lines. It was found that the derivatives with an aliphatic amino group at the 4-position are generally less toxic to normal cells than those with a benzylsulfanyl group. Moreover, compounds with bulky constituents exhibit better anticancer properties, though at a moderate level. The specific compounds were chosen due to their most promising IC50 concentration for in silico study. Furthermore, antimicrobial activity tests were performed against six strains of bacteria and one fungus. They demonstrated that only derivatives with at least three carbon chain amino groups at the 4-position have weak antibacterial properties, and only the derivative with 4-benzylsulfanyl constituent exhibits any antifungal action.

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Research developments in the syntheses, anti-inflammatory activities and structure–activity relationships of pyrimidines

Abstract: This review sums up recent developments in the syntheses, anti-inflammatory activities, and structure–activity relationship (SAR) studies of pyrimidine derivatives.

Cited by 69 publications

References 154 publications

Non-steroidal anti-inflammatory drugs: recent advances in the use of synthetic COX-2 inhibitors

Non-steroidal anti-inflammatory drugs: recent advances in the use of synthetic COX-2 inhibitors

Utility of [4‐(3‐methoxyphenyl)pyrimidin‐2‐yl]cyanamide in synthesis of some heterocyclic compounds

Synthesis, Crystal Structure, and Biological Evaluation of Novel 5-Hydroxymethylpyrimidines

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