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

Abstract

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).

Synthesis, reactions, and spectral characterization of some new biologically active compounds derived from thieno[2,3‐c]pyrazole‐5‐carboxamide

“…Furthermore, thienopyrimidines have anticipated biological activity . In the light of the previous biological importance and in our ongoing endeavor to create new pyrazole thienopyrimidine‐based hybrids, we have synthesized here a series of new heterocyclic compounds isoindole, pyrazole, and triazepine attached or fused to the pyrazolothienopyrimidine ring system. Subsequently, due to the resistance of most bacterial and fungal strains to the current antimicrobial therapy, we are interested in synthesizing more effective agents.…”

Synthesis and fluorescent properties of some Furan‐tagged Thieno[2,3‐d]pyrimidines and Thieno[2,3‐d:4,5‐d']dipyrimidines

“…1 H NMR spectrum of 2b displayed a D 2 O exchangeable singlet at δ = 6.72 ppm for NH 2 ; in addition to a singlet at δ = 2.90 ppm for the pyrimidine CH 3 , while the furan H appear as multiplet signals in the region δ = 6.83-7.97 ppm. Its 13 C NMR showed one sp 3 signal at δ = 24.16 ppm for CH 3 ; in addition to the other expected sp and sp 2 signals. Also, IR spectrum clarified absorption bands at 3327, 3228, 2197 cm −1 for NH 2 and C N functions, respectively.…”

“…This result was confirmed by 1 H NMR, which displayed two new singlets at δ = 3.40 and 12.93 ppm for CH 2 CN and NH. Also, its 13 C NMR spectrum showed two sp 3…”

“…The high relevance of thienopyrimidine scaffolds is attributed to their wide applications in many aspects, particularly in the therapeutic field. Many of these compounds were reported to act as antimicrobial, [1][2][3] analgesic, [4] anticancer, [5] anti-inflammatory, [6] antihypertensive, [7] antioxidant, [8] anti-avian influenza, [9] antiproliferative, [10] anti-HIV, [11] and antidiabetic [12] agents. Additionally; thienopyrimidine scaffolds with appropriate absorption and emission wavelengths act as fluorophores.…”

Synthesis and Antibacterial Activities of Different Five-Membered Heterocyclic Rings Incorporated with Pyridothienopyrimidine

“…1 Among all fused thienoazines, pyridothienopyrimidine derivatives have been studied the most. These derivatives act as bactericides 2−6 fungicides, 2−6 antiprotozoals, 7 or immunomodulators; exhibit antianaphylactic, antiallergic, 8 anticonvulsive, 9 analgetic, or anti-inflammatory activities; 10,11 and are used as intermediate products in chemical pharmaceutical industry. 1 In addition to antimicrobial, 2−6 anticonvulsant, 9 and anticancer activities 12−17 of pyridothienopyrimidine deriva-tives, recent studies showed that they have the ability to specifically activate testicular steroidogenesis without affecting thyroid functions.…”