Design, Synthesis, and Antimicrobial Evaluation of Novel Thienopyrimidines and Triazolothienopyrimidines

Mahmoud, Mahmoud R.; El‐Azm, Fatma S. M. Abu; Ali, Amira T.; Ali, Yasmeen M.

doi:10.1080/00397911.2014.999340

Cited by 21 publications

(13 citation statements)

References 21 publications

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“…Thienopyrimidines, including the three fundamental systems (thieno[2,3‐ d ]pyrimidine, thieno[3,2‐ d ]pyrimidine, and thieno[3,4‐ d ]pyrimidine), are among those fused pyrimidines that are found to have a wide variety of pharmacological activities. Many thienopyrimidines have been found to exhibit a variety of pronounced activities as antimicrobial , anticancer , and antiviral agents. Moreover, the literatures advertised that thienopyrimidines bearing furan moiety (Fig.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Some Novel Furan‐tagged Thienopyrimidine Derivatives as Antibacterial Agents

Hamid

Shehta

2018

Journal of Heterocyclic Chem

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Cyclization of 2‐furan‐2‐yl‐4‐mercapto‐6‐methylpyrimidine‐5‐carbonitrile 1 with ethyl chloroacetate gave o‐aminoester thienopyrimidine derivative 3, which was reacted with a variety of reagents to give a series of novel thienopyrimidines including tetrazolyl thienopyrimidine, pyrrolylthienopyrimidine, pyrimidothienotriazine, and thienodipyrimidines. Some of the synthesized compounds were tested for their antibacterial activities against Gram‐positive and Gram‐negative bacteria.

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Section: Introductionmentioning

confidence: 99%

Synthesis of Some Novel Furan‐tagged Thienopyrimidine Derivatives as Antibacterial Agents

Hamid

Shehta

2018

Journal of Heterocyclic Chem

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“…Therefore, the discovery of methods to prepare new compounds to be used as anti‐inflammatory drugs is one of the main objectives of this research. In the last few years, thienopyrimidines and their derivatives have been shown to display therapeutic activity as anti‐inflammatory, antimicrobial, antiviral, antioxidant, antitumor, and anticancer, as well as antidepressant, antiplatelet, antihypertensive, herbicidal, and plant growth regulatory properties . Recently, a large number of thienopyrimidines and fused thienopyrimidines were found to possess promising anti‐inflammatory and antimicrobial activities, as shown in Figure .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, reactions, and biological study of some new thienopyrimidine derivatives as antimicrobial and anti‐inflammatory agents

Tolba¹,

El‐Dean

Ahmed³

et al. 2018

J Chinese Chemical Soc

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Pyrimidine and thienopyrimidine derivatives play a very important role in organic chemistry because of their wide applications as bioactive compounds with multiple biological activities. However, a literature survey revealed that the merger of different groups in the thieno[2,3-d]pyrimidine heterocyclic ring enhances its antibacterial, antifungal and anti-inflammatory activities. This encouraged us to prepare a new series of thieno[2,3-d]pyrimidine heterocyclic compounds and to test them as antimicrobial and anti-inflammatory agents. These compounds have shown remarkable activity toward fungi, bacteria, and inflammation. Thus, these compounds have been prepared by the chloroacylation of 5-amino-4-phenyl-2-(p-tolylamino) thieno[2,3-d] pyrimidine-6-carboxamide (4) using chloroacetyl chloride under neat condition to afford the target compound (6), which was used as precursor for the synthesis of a number of bioactive compounds. Thus reaction of the chloromethylpyrimidine derivative (6) with triphenylphosphine in dry benzene gave the corresponding ((4-oxo-9-phenyl-7-(p-tolylamino)-3,4-dihydropyrimido[4 0 ,5 0 :4,5]thieno [2,3-d]pyrimidin-2-yl)methyl) triphenylphosphonium chloride (7). Compounds 8a-8c and 9a-9c were obtained by the reaction of 7 with some selected aromatic aldehydes and ketones in methanol and sodium methoxide under Wittig reaction condition. The structures of the all new synthesized compounds were established on the basis of their analytical and spectral data (IR, 1 H NMR, 13 C NMR, and MS).

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“…In the past few years, thienopyrimidines and fused thienopyrimidine derivatives have attracted great attention owing to their inspiring array of pharmacological activities . Thienopyrimidines are interesting heterocyclic compounds, and a lot of derivatives of these compounds display therapeutic activity as antimicrobial , antiviral , anti‐inflammatory , antidiabetic , antioxidant , antitumor , anticancer agents , and antimalarial . Some thienopyrimidine used as analgesic .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of New Fused Thienopyrimidines Derivatives as Anti‐inflammatory Agents

Tolba

Ahmed

El‐Dean

et al. 2017

Journal of Heterocyclic Chem

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5‐Amino‐2‐(p‐tolylamino)‐4‐phenylthieno[2,3‐d]pyrimidine‐6‐carbonitrile 9, which was synthesized by an innovative method, was used as a versatile precursor for synthesizing pyrimido‐thienopyrimidine, triazolopyrimidothienopyrimidine, and pyrimidothienotriazine compounds. Thus, reaction of aminothienopyrimidinecarbonitrile 9 with chloroacetylchloride in dioxane afforded the chloroacetylaminocarbonitrile derivative 10, which underwent nucleophilic substitution reactions with various primary and secondary amines gave the corresponding N‐alkyl‐(aryl)amino acetamides 11a,b. On the other hand, the reaction of aminocarbonitrile 9 with triethyl orthoformate followed by cyclization with hydrazine yielded an aminoiminopyrimidine derivative 13. The latter was used as versatile precursor for synthesis of new heterocyclic compounds. The structures of all the new compounds have been established on the basis of their analytical and spectral data (IR, 1H NMR, 13C NMR, and MS). Some of the synthesized compounds were evaluated in vitro for their anti‐inflammatory activity. All the tested compounds exhibited remarkable anti‐inflammatory activity.

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Design, Synthesis, and Antimicrobial Evaluation of Novel Thienopyrimidines and Triazolothienopyrimidines

Abstract: of 2-methyl-3-(2-oxo-2H-chromene)amido-5,6,7,8-tetrahydro-4H-benzo thieno[2,3d]pyrimidin-4-one 4A mixture of thienopyrimidine 3 (1 g, 3.3 mmol) and salicyaldehyde (0.4 ml, 3.3 mmol) in the presence of catalytic amount of piperidine (0.5 ml) in dioxane (10 ml) was refluxed for 4hrs. The

Cited by 21 publications

References 21 publications

Synthesis of Some Novel Furan‐tagged Thienopyrimidine Derivatives as Antibacterial Agents

Synthesis of Some Novel Furan‐tagged Thienopyrimidine Derivatives as Antibacterial Agents

Synthesis, reactions, and biological study of some new thienopyrimidine derivatives as antimicrobial and anti‐inflammatory agents

Synthesis of New Fused Thienopyrimidines Derivatives as Anti‐inflammatory Agents

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