70638-53-8Relevant academic research and scientific papers
Hydrotalcites as catalyst in suitable multicomponent synthesis of uracil derivatives
Nope, Eliana,Sathicq, ángel G.,Martínez, José J.,Rojas, Hugo,Romanelli, Gustavo
, p. 126 - 135 (2021/02/05)
Uracil compounds participate in a wide range of biological activities; however, reports on their synthesis using heterogeneous catalysts are scarce. In this work, the multicomponent synthesis of uracil derivatives assisted by layered double hydroxides (LDH) was studied under green chemistry conditions. The incorporation of Ni2+ or Co2+ was successfully performed by co-precipitation method. The yields to uracil derivatives are associated with the presence of weak basic sites and a better interaction of the reagents when the reaction is carried out in solvent-free conditions. The reaction pathway involves the formation of an enone between benzaldehyde and ethyl cyanoacetate, and subsequent reaction with urea, which is assisted by the presence of a basic catalyst. The scope of this synthesis is illustrated with nine examples.
Synthesis, antibacterial activities and molecular docking study of thiouracil derivatives containing oxadiazole moiety
Cui, Peng-Lei,Zhang, Di,Guo, Xiu-Min,Ji, Shu-Jing,Jiang, Qing-Mei
supporting information, p. 1754 - 1762 (2021/04/09)
A series of novel thiouracil derivatives 9 containing an oxadiazole moiety have been synthesized by structural modification of a lead SecA inhibitor, 2. These compounds have been evaluated for their antibacterial activities against Bacillus amyloliquefaciens, Staphylococcus aureus and Bacillus subtilis. Among them, compounds 9g and 9n exhibited promising antibacterial activities against the tested strains. Compound 9g was also tested for its inhibitory activities against SecA ATPase, and the IC50 value of compound 9g was 19.9 μg/mL, lower than that of compound 2 (20.8 μg/mL). Molecular docking work indicates that compound 9g likely occupies the pocket formed by SecA IRA2 and NBD domain.
Design, Synthesis and Antibacterial Activity of Novel Pyrimidine-Containing 4H-Chromen-4-One Derivatives**
Chen, Mei,He, Ming,Liu, Tingting,Peng, Feng,Su, Shijun,Tang, Xuemei,Xie, Chengwei,Xue, Wei,Zhan, Wenliang,Zhou, Qing
, (2021/07/12)
A series of pyrimidine-containing 4H-chromen-4-one derivatives were designed and synthesized by combining bioactive substructures. Preliminary biological activity results showed that most of the compounds displayed significant inhibitory activities in vit
Substituted pyrimidine-containing myricetin derivative as well as preparation method and application thereof
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Paragraph 0029; 0034-0035; 0048; 0054-0055, (2020/12/05)
The invention discloses a substituted pyrimidine-containing myricetin derivative as well as a preparation method and application thereof. The general structural formula of the myricetin derivative isshown in the specification, R represents a substituted phenyl group or a substituted aromatic heterocyclic group; n is the number of carbon in a carbon chain and is 2-6; wherein the substituted phenylgroup is on the ortho-, meta-and para- position of a benzene ring and contains C1-6 alkyl groups, C1-6 alkoxyl groups, nitro groups, halogen atoms and hydrogen atoms; the aromatic heterocyclic groupis thienyl, furyl, pyrrolyl or pyridyl; and substituent groups on substituted aromatic heterocycle are ortho-, meta-and para- positions and contain C1-6 alkyl groups, C1-6 alkoxyl groups, nitro groups, halogen atoms and hydrogen atoms. The derivative can well inhibit the activity of pathogenic bacteria of plants.
New 2,4-disubstituted-2-thiopyrimidines as VEGFR-2 inhibitors: Design, synthesis, and biological evaluation
Abdel-Mohsen, Heba T.,Girgis, Adel S.,Mahmoud, Abeer E. E.,Ali, Mamdouh M.,El Diwani, Hoda I.
, (2019/09/06)
A new series of 2,4-disubstituted-2-thiopyrimidines 6a–t, 9a, and 9b was efficiently designed and synthesized as antiangiogenic and cytotoxic agents. Compounds 6j, 6l, and 6d showed IC50 values of 1.23, 3.78, and 3.84 μM, respectively, against the vascular endothelial growth factor receptor-2 (VEGFR-2). Most of the synthesized 2-thiouracils showed antiproliferative activity against the HepG2 cell line (hepatocellular carcinoma) in the micromolar range, for instance, 9b, 6l, 6m, 6n, and 6j displayed IC50 = 7.92, 8.35, 8.51, 9.59, and 13.06 μM, respectively, relative to sorafenib (III; IC50 = 10.99 μM). Also, compounds 6j, 9a, 6m, and 6s (IC50 = 15.21, 16.96, 17.68, and 18.15 μM, respectively) are the most potent compounds against the UO-31 cell line. Further evaluation of the effect of the synthesized candidates on VEGFR-2 in the HepG2 cell line demonstrated that compounds 6j and 6l exhibit VEGFR-2 inhibitory activity of 87% and 84%, respectively, relative to sorafenib (III; 92%). In silico docking of the synthesized hits into the binding site of VEGFR-2 showed their ability to perform the main binding interactions with the key amino acids in the binding site. Studying the in silico predicted ADME (absorption, distribution, metabolism, and excretion) parameters for the synthesized thiouracils demonstrated that they have favorable pharmacokinetic and drug-likeness properties. These results demonstrate that the 2,4-disubstituted thiouracils 6 and 9 have not only favorable antiangiogenic and antiproliferative activity but also satisfy the criteria required for the development of orally bioavailable drugs. Consequently, they represent a biologically active scaffold that should be further optimized for future discovery of potential hits.
Part III: Novel checkpoint kinase 2 (Chk2) inhibitors; design, synthesis and biological evaluation of pyrimidine-benzimidazole conjugates
Galal, Shadia A.,Khattab, Muhammad,Shouman, Samia A.,Ramadan, Raghda,Kandil, Omaima M.,Kandil, Omnia M.,Tabll, Ashraf,El Abd, Yasmine S.,El-Shenawy, Reem,Attia, Yasmin M.,El-Rashedy, Ahmed A.,El Diwani, Hoda I.
, p. 687 - 708 (2018/02/10)
Recently a dramatic development of the cancer drug discovery has been shown in the field of targeted cancer therapy. Checkpoint kinase 2 (Chk2) inhibitors offer a promising approach to enhance the effectiveness of cancer chemotherapy. Accordingly, in this study many pyrimidine-benzimidazole conjugates were designed and twelve feasible derivatives were selected to be synthesized to investigate their activity against Chk2 and subjected to study their antitumor activity alone and in combination with the genotoxic anticancer drugs cisplatin and doxorubicin on breast carcinoma, (ER+) cell line (MCF-7). The results indicated that the studied compounds inhibited Chk2 activity with high potency (IC50 = 5.56 nM - 46.20 nM). The studied candidates exhibited remarkable antitumor activity against MCF-7 (IG50 = 6.6 μM - 24.9 μM). Compounds 10a-c, 14 and 15 significantly potentiated the activity of the studied genotoxic drugs, whereas, compounds 9b and 20–23 antagonized their activity. Moreover, the combination of compound 10b with cisplatin revealed the best apoptotic effect as well as combination of compound 10b with doxorubicin led to complete arrest of the cell cycle at S phase where more than 40% of cells are in the S phase with no cells at G2/M. Structure-activity relationship was discussed on the basis of molecular modeling study using Molecular modeling Environment program (MOE).
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 (2017/01/21)
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 convenient synthesis of pyrimidinone and pyrimidine containing bisheteroarenes and analogs
Maurya, Hardesh K.,Gupta, Atul
, p. 22106 - 22114 (2014/06/23)
The synthesis of pyrimidinone containing bisheteroarenes (3) and related analogs (9 and 10) by the reaction of active methylenes or substituted methyl acrylate with nitrogen containing precursors viz. amidines, or thiourea in water as well as other organic solvents was studied. Synthesized compounds have further been explored for the synthesis of diversified pyrimidines 4, 6-8, 11, 12 and 14 through a sequential approach. This journal is the Partner Organisations 2014.
Synthesis of a 2,4,6-trisubstituted 5-cyano-pyrimidine library and evaluation of its immunosuppressive activity in a Mixed Lymphocyte Reaction assay
Stella, Alessandro,Van Belle, Kristien,De Jonghe, Steven,Louat, Thierry,Herman, Jean,Rozenski, Jef,Waer, Mark,Herdewijn, Piet
, p. 1209 - 1218 (2013/03/28)
A series of novel pyrimidine analogues were synthesized and evaluated for immunosuppressive activity in the Mixed Lymphocyte Reaction assay, which is well-known as the in vitro model for in vivo rejection after organ transplantation. Systematic variation of the substituents at positions 2, 4 and 6 of the pyrimidine scaffold led to the discovery of 2-benzylthio-5-cyano-6-(4- methoxyphenyl)-4-morpholinopyrimidine with an IC50 value of 1.6 μM in the MLR assay.
Laccase-catalyzed domino reaction between catechols and 6-substituted 1,2,3,4-tetrahydro-4-oxo-2-thioxo-5-pyrimidinecarbonitriles for the synthesis of pyrimidobenzothiazole derivatives
Abdel-Mohsen, Heba T.,Conrad, Juergen,Beifuss, Uwe
, p. 7986 - 8003 (2013/09/12)
The laccase-catalyzed domino reaction between catechols and 6-substituted 1,2,3,4-tetrahydro-4-oxo-2-thioxo-5-pyrimidinecarbonitriles using aerial O 2 as the oxidant delivers new pyrimidobenzothiazole derivatives. The complete structure elucida
