14346-24-8Relevant articles and documents
Structure based design, synthesis and evaluation of new thienopyrimidine derivatives as anti-bacterial agents
Malasala, Satyaveni,Polomoni, Anusha,Ahmad, Md. Naiyaz,Shukla, Manjulika,Kaul, Grace,Dasgupta, Arunav,Chopra, Sidharth,Nanduri, Srinivas
, (2021)
TrmD, tRNA-(N1G37) methyltransferase, a member of SpoU-TrmD (SPOUT) RNA methyltransferase family, is one of the key enzymes responsible for the growth of Staphylococcus aureus, Pseudomonas aeruginosa, Mycobacterium tuberculosis (Mtb) and Mycobacterium abscessus (Mab). A number of TrmD inhibitors including thienopyrimidines and fused thienopyrimidines are reported as potent anti-bacterial and anti-mycobacterial agents. In the current study, a library of ~200 structurally diverse thienopyrimidines were designed and subjected to preliminary in silico studies. 22 of the compounds were selected, synthesized and were evaluated for their inhibitory activities against a panel of pathogens consisting E. coli, S. aureus, K. pneuminiae, A. baumannii and P. aeruginosa and M. tuberculosis (ATCC 27294). Among the tested compounds, 13b, 18a-e were found to inhibit M. tuberculosis (ATCC 27294) with the MIC of 16-32 μg/mL. The compound 18f was found to be selective against S. aureus with the MIC of 4 μg/mL and moderate activity against M. tuberculosis. The selected compounds were further subjected to docking, 3D-QSAR and ADME/T studies to understand the mechanism of action and also their physico chemical profile.
Synthesis and anticancer activities of novel (tetrahydrobenzo [4,5] thieno [2,3-d] pyrimidine-4-yl)-pyrolidine-2-carboxylic acid derivatives
Pavase, Laxmikant S.,Mane, Dhananjay V.
, p. 2380 - 2391 (2016)
Cancer chemotherapy has been one of the major medical advances in the last few decades. The medications involved in treatment have a narrow therapeutic index, and often the responses produced are only just palliative as well as unpredictable. In contrast,
Thienopyrimidine sulphonamide hybrids: Design, synthesis, antiprotozoal activity and molecular docking studies
Leeza Zaidi, Saadia,Agarwal, Subhash M.,Chavalitshewinkoon-Petmitr, Porntip,Suksangpleng, Thidarat,Ahmad, Kamal,Avecilla, Fernando,Azam, Amir
, p. 90371 - 90383 (2016)
A series of hybrid compounds containing the thienopyrimidine scaffold as a DHFR inhibitor fused with a bioactive sulphonamide piperazine skeleton were synthesized and evaluated against the chloroquine and pyrimethamine resistant K1 strain of Plasmodium falciparum and the HM1:1MSS strain of Entamoeba histolytica, respectively. A few of the compounds showed better results than the standard drugs. The toxicity of the hybrids was measured on the Chinese hamster cell line. The majority of the compounds had low toxicity. The binding modes of the most potent antimalarial compounds (5, 6 and 8) were also investigated against PfDHFR using molecular docking and enzyme binding studies, whereby 5 and 6 were found to the most promising against PfDHFR. The present studies suggest that these hybrids might be possible antiprotozoal lead compounds worth further investigation.
Hybrids of thienopyrimidinones and thiouracils as anti-tubercular agents: SAR and docking studies
Pisal, Mahesh M.,Nawale, Laxman U.,Patil, Manoj D.,Bhansali, Sujit G.,Gajbhiye, Jayant M.,Sarkar, Dhiman,Chavan, Subhash P.,Borate, Hanumant B.
, p. 459 - 469 (2017)
A number of hybrid molecules containing thienopyrimidinones and thiouracil moieties were designed, synthesized and tested against Mycobacterium tuberculosis H37Ra wherein it was observed that the compounds 11–14 exhibited antitubercular activity in?vitro
A facile synthesis of some novel fused [1,2,4]triazolo[3,4-b][1,3,4] thiadiazol derivatives
Nagaraju, Kerru,Kotaiah, Yalagala,Sampath, Chinnam,Harikrishna, Nallapaneni,Rao, Chunduri Venkata
, p. 264 - 275 (2013)
A series of novel 3-[6-(4-substituted phenyl)-[1,2,4]triazolo[3,4-b][1,3,4] thiadiazol-3-ylmethyl]-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4(3H) -one derivatives (7a-7h) have been synthesized from 2-amino-4,5,6,7- tetrahydrobenzo[b]thiophene-3-carbonitrile (1) through a multi-step reaction sequence. The key intermediate (6) on condensation with various substituted aromatic carboxylic acids in the presence of phosphorus oxychloride afforded the series of title compounds (7a-7h). The structures of all newly synthesized compounds were established on the basis of their IR, 1H-NMR, 13C-NMR and liquid chromatography mass spectrometry spectral data.
Structure based design of selective SHP2 inhibitors by De novo design, synthesis and biological evaluation
Liu, Wen-Shan,Jin, Wen-Yan,Zhou, Liang,Lu, Xing-Hua,Li, Wei-Ya,Ma, Ying,Wang, Run-Ling
, p. 759 - 774 (2019)
SHP2 phosphatase, encoded by the PTPN11 gene, is a non-receptor PTP, which plays an important role in growth factor, cytokine, integrin, hormone signaling pathways, and regulates cellular responses, such as proliferation, differentiation, adhesion migrati
Design and synthesis of new thiophene/ thieno[2,3-d]pyrimidines along with their cytotoxic biological evaluation as tyrosine kinase inhibitors in addition to their apoptotic and autophagic induction
Alkahtani, Manal Mubarak,Altwaijry, Najla,Attallah, Nashwah G. M.,Elmongy, Elshaymaa I.,Henidi, Hanan Ali
, (2021/12/31)
This work describes the synthesis and anticancer activity against kinase enzymes of newly designed thiophene and thieno[2,3-d]pyrimidine derivatives, along with their potential to activate autophagic and apoptotic cell death in cancer cells. The designed compounds were scanned for their affinity for kinases. The results were promising with affinity ranges from 46.7% to 13.3%. Molecular docking studies were performed, and the compounds were then screened for their antiproliferative effects. Interestingly, compounds 8 and 5 resulted in higher cytotoxic effects than the reference standard against MCF-7 and HepG-2. The compounds were evaluated for their induction of apoptosis and/or necrosis on HT-29 and HepG-2. Three compounds induced significant early apoptosis compared to untreated control HT-29 cells, and four derivatives were more significant compared to untreated HepG-2 cells. We further investigated the effect of four compounds on the autophagy process within HT-29, HepG-2, and MCF-7 cells with flow cytometry. Similar to the apoptosis results, compound 5 showed the highest autophagic induction among all compounds. The potential inhibitory activity of the synthesized compounds on kinases was assessed. Screened compounds showed inhibition activity ranging from 41.4% to 83.5%. Compounds recorded significant inhibition were further investigated for their specific FLT3 kinase inhibitory activity. Noticeably, Compound 5 exhibited the highest inhibitory activity against FLT3.
Synthesis of New Thieno[2,3-d]pyrimidines Containing a 1,2,3-Triazole Ring and Their Therapeutic Response in NCI-60 Cell Line Panel
Baluja, S. H.,Bhensdadia, K. A.,Lalavani, N. H.
, p. 1668 - 1677 (2021/12/13)
Abstract: A series of new tetrahydro[1]benzothieno[2,3-d]pyrimidines containing a 1,2,3-triazole fragment linkedthrough an oxymethylene spacer have been synthesized by click reaction of4-(prop-2-yn-1-yloxy)-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidines with various aryl and alkyl azides inthe presence of copper sulfate and sodium ascorbate as a catalyst. Thestructures of the synthesized compounds were characterized by variousspectroscopic techniques (1H and13C NMR, FT-IR, and mass spectrometry), and theirin vitro anticancer activity against NCI-60 human tumor cell lines wasevaluated. Among the compounds tested, N-(pyridine-3-yl)-acetamide derivative exhibited significantactivity against several cancer cell lines, including SF-539 (CNS cancer),HCT-116 (colon cancer), OVCAR-8 (ovarian cancer), PC-3 (prostate cancer), andCCRF-CEM (leukemia).
