Abstract: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.
“…Initially, Thieno[2,3‐ d ]pyrimidines 2a,b were synthesized via base‐initiated cyclization of 2‐furan‐2‐yl‐4‐mercapto‐6‐methylpyrimidine‐5‐carbonitrile 1 with ethyl chloroacetate and/or chloroacetonitrile.…”
Section: Resultsmentioning
confidence: 99%
“…Hydrazinolysis of o ‐aminoester 2a afforded acid hydrazide 3, which upon refluxing with formic acid, triethyl orthoformate, and acetic anhydride yielded thieno[2,3‐ d ,4,5‐ d' ]dipyrimidines 4 to 6 . The structures of these compounds were confirmed by their spectral data; 1 H NMR spectrum of 6 (as an example) displayed three singlets at δ = 2.46, 2.99 and 3.08 ppm for COCH 3 and two pyrimdineCH 3 .…”
Section: Resultsmentioning
confidence: 99%
“…Elemental analyses and IR spectra were carried out at Micro Analytical Center, Cairo University. Compounds 2a and 3 were synthesized as reported by one of us …”
Section: Methodsmentioning
confidence: 99%
“…Moreover, some fluorescent compounds are utilized in studying the environmental pollution . Thus, in the light of these reports and in continuation of our studies on the synthesis and properties of furan‐tagged condensed pyrimidines, we report herein a synthetic approach for a highly fluorescent series of these compounds.…”
Intermolecular cyclization of pyrimidinethiol 1 with ethyl chloroacetate and chloroacetonitrile furnished thieno[2,3-d]pyrimidines 2a,b. Hydrazinolysis of o-aminoester 2a gave acid hydrazide 3, which was cyclized with various electrophilic reagents including formic acid, triethyl orthoformate, acetic anhydride, p-chlorobenzaldehyde then triethyl orthoformate, carbon disulfide, and acetylacetone affording thienopyrimidine derivatives 4 to 10. Another thienopyrimidine series could be obtained via treatment of o-aminocarbonitrile 2b with a variety of reagents giving derivatives 11 to 17. The fluorescent measurements for a group of the synthesized compounds at room temperature demonstrated high fluorescent properties.
“…Initially, Thieno[2,3‐ d ]pyrimidines 2a,b were synthesized via base‐initiated cyclization of 2‐furan‐2‐yl‐4‐mercapto‐6‐methylpyrimidine‐5‐carbonitrile 1 with ethyl chloroacetate and/or chloroacetonitrile.…”
Section: Resultsmentioning
confidence: 99%
“…Hydrazinolysis of o ‐aminoester 2a afforded acid hydrazide 3, which upon refluxing with formic acid, triethyl orthoformate, and acetic anhydride yielded thieno[2,3‐ d ,4,5‐ d' ]dipyrimidines 4 to 6 . The structures of these compounds were confirmed by their spectral data; 1 H NMR spectrum of 6 (as an example) displayed three singlets at δ = 2.46, 2.99 and 3.08 ppm for COCH 3 and two pyrimdineCH 3 .…”
Section: Resultsmentioning
confidence: 99%
“…Elemental analyses and IR spectra were carried out at Micro Analytical Center, Cairo University. Compounds 2a and 3 were synthesized as reported by one of us …”
Section: Methodsmentioning
confidence: 99%
“…Moreover, some fluorescent compounds are utilized in studying the environmental pollution . Thus, in the light of these reports and in continuation of our studies on the synthesis and properties of furan‐tagged condensed pyrimidines, we report herein a synthetic approach for a highly fluorescent series of these compounds.…”
Intermolecular cyclization of pyrimidinethiol 1 with ethyl chloroacetate and chloroacetonitrile furnished thieno[2,3-d]pyrimidines 2a,b. Hydrazinolysis of o-aminoester 2a gave acid hydrazide 3, which was cyclized with various electrophilic reagents including formic acid, triethyl orthoformate, acetic anhydride, p-chlorobenzaldehyde then triethyl orthoformate, carbon disulfide, and acetylacetone affording thienopyrimidine derivatives 4 to 10. Another thienopyrimidine series could be obtained via treatment of o-aminocarbonitrile 2b with a variety of reagents giving derivatives 11 to 17. The fluorescent measurements for a group of the synthesized compounds at room temperature demonstrated high fluorescent properties.
“…The structural and isoelectronic characteristics of thienopyrimidine-containing compounds are similar to those of purine and they have become an attractive structural feature in the production of pharmaceutical drugs [10,11]. Thienopyrimidines have been demonstrated to have significant and various pharmacological properties, such as antibacterial [12][13][14], antiviral [15,16], antiinflammatory [17,18], antiprotozoal [19], and anticancer activities [20][21][22][23]. Figure 1 represents some thienopyrimidinecontaining drugs with varying profiles of biological activity.…”
Thienopyrimidine derivatives hold a unique place between fused pyrimidine compounds. They are important and widely represented in medicinal chemistry as they are structural analogs of purines. Thienopyrimidine derivatives have various biological activities. The current review discusses different synthetic methods for the preparation of heterocyclic thienopyrimidine derivatives. It also highlights the most recent research on the anticancer effects of thienopyrimidines through the inhibition of various enzymes and pathways, which was published within the last 9 years.
Graphical Abstract
Inflammation is an essential body immune system response against various infections and tissue injuries and maintains normal homeostasis. Alterations in inflammatory responses lead to multiple disorders like heart diseases, obesity, diabetes, cancer, stroke, and neurodegenerative disorders. Cyclooxygenases (COXs), the enzymes, exist in two isoforms (COX‐1 and COX‐2) that catalyze the rate‐determining step of prostaglandin biogenesis and play a significant role in inflammation. COX‐2 inhibitors, although effective anti‐inflammatory agents are considered to be highly unsafe for long‐term usage due to their possible side and adversative effects. Recently, fused‐thienopyrimidines have emerged as a privileged scaffold with excellent anti‐inflammatory potential. In the present review, we have emphasized the recent developments in the design and synthetic strategies of fused‐thienopyrimidine derivatives and their detailed structure‐activity‐relationship (SAR) studies. The primary goal of this review is to provide restructuring knowledge about this template, which could prove beneficial and valuable for chemists working in the anti‐inflammatory area.
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