Synthesis and pharmacological evaluation of novel thienopyrimidine and triazolothienopyrimidine derivatives

Mulla, Jameel Ahmed S.; Khazi, Mohammed Iqbal; Panchamukhi, Shridhar I.; Gong, Young‐Dae; Khazi, Imtiyaz Ahmed M.

doi:10.1007/s00044-013-0900-1

Cited by 23 publications

(6 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Synthesis of 2-amino-4,5,6,7-tetrahydrobenzo[2,3b]thiophene-3-carbonitrile (1) 2-Amino-4,5,6,7-tetrahydrobenzo[2,3-b]thiophene-3-carbonitrile (1) was prepared by means of Gewald's reaction as reported in the literature (20)(21)(22). Formation of 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile (1) was characterized by the presence of a band at 2210 cm À1 due to a cyano group and N-H stretching bands at 3325 and 3209 cm À1 in their IR spectra.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and Evaluation of Biological and Antitumor Activities of Tetrahydrobenzothieno[2,3‐d]Pyrimidine Derivatives as Novel Inhibitors of FGFR1

Wang

Chen

et al. 2016

Chem Biol Drug Des

View full text Add to dashboard Cite

A series of tetrahydrobenzothieno[2,3-d]pyrimidine derivatives were designed, synthesized, and evaluated as inhibitors of FGFR1. These analogs were synthesized via Gewald's reaction under mild conditions. The structures of the synthesized compounds were characterized by spectroscopic data (IR, (1) H NMR and MS). Their antitumor activities were evaluated against H460, A549 and U251 cell lines in vitro. Results revealed that the tested compounds showed moderate antitumor activities. Structure-activity relationship analyses indicated that compounds with an aromatic ring substituted in the C-2 position or with larger molecules such as 3g, 4c, and 7 were more effective than others. The compound, 3g (78.8% FGFR1 inhibition at 10 μm), was identified to have the most potent antitumor activities, with IC50 values of 7.7, 18.9, and 13.3 μm against the H460, A549, and U251 cell lines, respectively. Together, the results suggested that tetrahydrobenzothieno[2,3-d]pyrimidine derivatives may serve as a potential agent for the treatment of FGFR1-mediated cancers.

show abstract

Section: Chemistrymentioning

confidence: 99%

Synthesis and Evaluation of Biological and Antitumor Activities of Tetrahydrobenzothieno[2,3‐d]Pyrimidine Derivatives as Novel Inhibitors of FGFR1

Wang

Chen

et al. 2016

Chem Biol Drug Des

View full text Add to dashboard Cite

show abstract

“…Reported thienopyrimidines, I and II displayed promising anticancer and kinase inhibitory activity against EGFR 26,27 (Figure 1). Furthermore, compounds possessing thienopyrimidine motif were reported with interesting bioactivities such as anticancer 28,29 , antiviral 30 , antibacterial 31 , and anti-inflammatory 32 activities. Different glycosyl heterocycles have been synthesised and revealed potential anticancer and enzyme inhibition activities providing essential roles in biological systems, and glycosides possessing the 1,2,3-triazole core, e.g.…”

Section: Introductionmentioning

confidence: 99%

Click chemistry based synthesis, cytotoxic activity and molecular docking of novel triazole-thienopyrimidine hybrid glycosides targeting EGFR

Khattab

Alshamari²,

Hassan

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

View full text Add to dashboard Cite

show abstract

“…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

View full text Add to dashboard Cite

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).

show abstract

Synthesis and pharmacological evaluation of novel thienopyrimidine and triazolothienopyrimidine derivatives

Cited by 23 publications

References 20 publications

Synthesis and Evaluation of Biological and Antitumor Activities of Tetrahydrobenzothieno[2,3‐d]Pyrimidine Derivatives as Novel Inhibitors of FGFR1

Synthesis and Evaluation of Biological and Antitumor Activities of Tetrahydrobenzothieno[2,3‐d]Pyrimidine Derivatives as Novel Inhibitors of FGFR1

Click chemistry based synthesis, cytotoxic activity and molecular docking of novel triazole-thienopyrimidine hybrid glycosides targeting EGFR

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

Contact Info

Product

Resources

About