588676-51-1Relevant academic research and scientific papers
Design, synthesis, DFT study and antifungal activity of the derivatives of pyrazolecarboxamide containing thiazole or oxazole ring
Yan, Zhongzhong,Liu, Aiping,Huang, Mingzhi,Liu, Minhua,Pei, Hui,Huang, Lu,Yi, Haibo,Liu, Weidong,Hu, Aixi
, p. 170 - 181 (2018/03/08)
Pyrazolecarboxamide fungicides are one of the most important classes of agricultural fungicides, which belong to succinodehydrogenase inhibitors (SDHIS). To discover new pyrazolecarboxamide analogues with broad spectrum and high activity, a class of new compounds of pyrazole carboxamide derivatives containing thiazole or oxazole ring were designed by scaffold hopping and bioisosterism, and 36 pyrazole carboxamide derivatives with antifungal activity were synthesized. Those compounds were evaluated against five phytopathogenic fungi, Gibberella zeae, Phytophythora capsici, Sclerotonia sclerotiorum, Erysiphe graminis and Puccinia sorghi. The results indicated that most of the compounds displayed good fungicidal activities, especially against E. graminis. Theoretical calculations were carried out at the B3LYP/6-31G (d, p) level and the full geometry optimization was carried out using the 6-31G (d, p) basis set, and the frontier orbital energy, atomic net charges, molecular docking were discussed, and the structure-activity relationships were also studied.
Design, synthesis and biological evaluation of 1H-pyrazole-5-carboxamide derivatives as potential fungicidal and insecticidal agents
Huang, Danling,Huang, Mingzhi,Liu, Weidong,Liu, Aiping,Liu, Xingping,Chen, Xiaoyang,Pei, Hui,Sun, Jiong,Yin, Dulin,Wang, Xiaoguang
, p. 2053 - 2061 (2017/09/30)
A series of novel 1H-pyrazole-5-carboxamide compounds containing the phenyl thiazole moiety were designed and synthesized by a facile method, and their structures were characterized by 1H NMR, mass spectrometry and elemental analysis. Bioassay results showed that most of the title compounds showed potent fungicidal activities against Erysiphe graminis and insecticidal activity against Aphis fabae. Especially, compound 9b has EC50 values of 3.04 mg/L against Erysiphe graminis, of which the fungicidal activity is better than that of the commercial fungicide Thifluzamide and Azoxystrobinare; compound 9l has LC50 values of 3.81 mg/L against Aphis fabae, which was comparable with the commercial insecticide Tolfenpyrad. It is suggested that 1H-pyrazole-5-carboxamide compounds containing the phenyl thiazole moiety could be considered as a precursor structure for further design of pesticides. Graphical Abstract: A series of novel 1H-pyrazole-5-carboxamide compounds containing the phenyl thiazole moiety were designed and synthesized by a facile method, and their structures were characterized by 1H NMR, mass spectrometry and elemental analysis. Bioassay results showed that most of the title compounds showed potent fungicidal activities against Erysiphe graminis and insecticidal activity against Aphis fabae. Especially, compound 9b has EC50 values of 3.04 mg/L against Erysiphe graminis, of which the fungicidal activity is better than that of the commercial fungicide Thifluzamide and Azoxystrobinare; compound 9l has LC50 values of 3.81 mg/L against Aphis fabae, which was comparable with the commercial insecticide Tolfenpyrad. It is suggested that 1H-pyrazole-5-carboxamide compounds containing the phenyl thiazole moiety could be considered as a precursor structure for further design of pesticides.[Figure not available: see fulltext.]
Synthesis and insecticidal activities of novel 1H-pyrazole-5-carboxylic acid derivatives
Huang, Danling,Liu, Aiping,Liu, Weidong,Liu, Xingping,Ren, Yeguo,Zheng, Xi,Pei, Hui,Xiang, Jun,Huang, Mingzhi,Wang, Xiaoguang
, p. 455 - 460 (2017/12/18)
Fourteen 1H-pyrazole-5-carboxylic acid derivatives containing oxazole and thiazole rings were synthesized and characterized by 1H NMR, mass spectrometry and elemental analysis. Most target compounds were obtained in overall yields in the range of 30-50%. The insecticidal activities of these new compounds against Aphis fabae were evaluated. The bioassays' results indicate that some of these compounds exhibit good activities, especially compound 7h which shows 85.7% mortality against A. fabae at a concentration of 12.5 mg/L. This activity is comparable to that of the commercial insecticide imidacloprid.
Agonists for the adenosine A1 receptor with tunable residence time. a case for nonribose 4-amino-6-aryl-5-cyano-2-thiopyrimidines
Louvel, Julien,Guo, Dong,Agliardi, Marta,Mocking, Tamara A. M.,Kars, Roland,Pham, Tan Phát,Xia, Lizi,De Vries, Henk,Brussee, Johannes,Heitman, Laura H.,Ijzerman, Adriaan P.
, p. 3213 - 3222 (2014/05/20)
We report the synthesis and evaluation of previously unreported 4-amino-6-aryl-5-cyano-2-thiopyrimidines as selective human adenosine A 1 receptor (hA1AR) agonists with tunable binding kinetics, this without affecting their nanomolar affinity for the target receptor. They show a very diverse range of kinetic profiles (from 1 min (compound 52) to 1 h (compound 43)), and their structure-affinity relationships (SAR) and structure-kinetics relationships (SKR) were established. When put in perspective with the increasing importance of binding kinetics in drug discovery, these results bring new evidence of the consequences of affinity-only driven selection of drug candidates, that is, the potential elimination of slightly less active compounds that may display preferable binding kinetics.
Synthesis and in-vitro cytotoxicity of poly-functionalized 4-(2-arylthiazol-4-yl)-4H-chromenes
Mahmoodi, Majid,Aliabadi, Alireza,Emami, Saeed,Safavi, Maliheh,Rajabalian, Saeed,Mohagheghi, Mohammad-Ali,Khoshzaban, Ahad,Samzadeh-Kermani, Alireza,Lamei, Navid,Shafiee, Abbas,Foroumadi, Alireza
, p. 411 - 416 (2011/08/05)
A new series of 4-aryl-4H-chromenes bearing a 2-arylthiazol-4-yl moiety at the 4-position were prepared as potential cytotoxic agents. The in-vitro cytotoxic activity of the synthesized 4-aryl-4H-chromenes was investigated in comparison with etoposide, a well-known anticancer drug, using MTT colorimetric assay. Among them, the 2-(2-chlorophenyl)thiazol-4-yl analog 4b showed the most potent activity against nasopharyngeal epidermoid carcinoma KB, medulloblastoma DAOY, and astrocytoma 1321N1, and compound 4d bearing a 2-(4-chlorophenyl) thiazol-4-yl moiety at the 4-position of the chromene ring exhibited the best inhibitory activity against breast cancer cells MCF-7, lung cancer cells A549, and colon adenocarcinoma cells SW480 with IC50 values less than 5 μM. The ability of compound 4b to induce apoptosis was confirmed in a nuclear morphological assay by DAPI staining in the KB and MCF-7 cells.
Synthesis and structure-activity relationships of 2-aryl-4-oxazolylmethoxy benzylglycines and 2-aryl-4-thiazolylmethoxy benzylglycines as novel, potent PPARα selective activators- PPARα and PPARγ selectivity modulation
Ye, Xiang-Yang,Chen, Stephanie,Zhang, Hao,Locke, Kenneth T.,O'Malley, Kevin,Zhang, Litao,Srivastava, Raijit,Miao, Bowman,Meyers, Daniel,Monshizadegan, Hossain,Search, Debra,Grimm, Denise,Zhang, Rongan,Lippy, Jonathan,Twamley, Celeste,Muckelbauer, Jodi K.,Chang, Chiehying,An, Yongmi,Hosagrahara, Vinayak,Zhang, Lisa,Yang,Mukherjee, Ranjan,Cheng, Peter T.W.,Tino, Joseph A.
supporting information; experimental part, p. 2933 - 2937 (2010/08/19)
The synthesis and follow-up SAR studies of our development candidate 1 by incorporating 2-aryl-4-oxazolylmethoxy and 2-aryl-4-thiazolylmethoxy moieties into the oxybenzylglycine framework of the PPARα/γ dual agonist muraglitazar is described. SAR studies indicate that different substituents on the aryloxazole/thiazole moieties as well as the choice of carbamate substituent on the glycine moiety can significantly modulate the selectivity of PPARα versus PPARγ. Potent, highly selective PPARα activators 2a and 2l, as well as PPARα activators with significant PPARγ activity, such as 2s, were identified. The in vivo pharmacology of these compounds in preclinical animal models as well as their ADME profiles are discussed.
Synthesis of new 1,4-dihydropyridine derivatives containing thiazolyl substituents
Bazargan, Leila,Shafiee, Abbas,Amini, Mohsen,Dezfouli, Ebrahim Bakhshi,Azizi, Ebrahim,Ghaffari, Seyed Mahmood
experimental part, p. 602 - 609 (2009/10/02)
A series of 4-[2-methyl (or aryl) thiazole-4-yl]-2,6-dimethyl-3,5-diacetyl (or dibenzoyl) 1,4-dihydropyridines were synthesized using a modified Hantzsch reaction involving the condensation of the corresponding aldehyde with acetyl acetone or benzoyl acetone. The preparation of the corresponding aldehydes (2-methylthiazole-4-carboxaldehyde and some 2-arylthiazole-4-carboxaldehydes) was achieved by a simplified protocol of the published synthesis.
Enhancement of the antibacterial activity of ciprofloxacin against Staphylococcus aureus by 3-alkyl esters and 3-aryl esters of hexahydroquinoline derivatives
Lak, Parnia,Amini, Mohsen,Safavi, Maliheh,Shafiee, Abbas,Shahverdi, Ahmad Reza
experimental part, p. 464 - 468 (2009/04/05)
In this study, 3-alkyl and 3-aryl esters of hexahydroquinoline derivatives were screened for their ability to decrease bacterial resistance to ciprofloxacin (CAS 85721-33-1), which is extensively used to treat bacterial infections. A group of 3-alkyl and 3-aryl esters of hexahydroquinoline derivatives in which 2-aryl thiazole is substituted at 4-position were synthesized. The enhancement of the antibacterial activity of ciprofloxacin by these new synthetic compounds was evaluated against a resistant clinical strain of Staphylococcus aureus. The agar disk diffusion method was used to determine the antibacterial activity of different synthetic compounds in the absence and presence of ciprofloxacin. These results indicate that the antibacterial effect of ciprofloxacin is enhanced by two 3-alkyl esters of hexahydroquinoline derivatives (7b-3 and 7b-4). The enhancing effect of 7b-4 on the antibacterial activity of ciprofloxacin was greater than that of compound 7b-3. In comparison to the other synthetic compounds, 7b-4 showed a 5.61-fold increase of the inhibition zone on the ciprofloxacin supplemented plates. The result demonstrated that compounds 7b (3 and 4) could serve as valuable probes to study the structure-function relationships of agents that reverse the resistance to ciprofloxacin. ECV Editio Cantor Verlag.
Design, synthesis, and biological evaluation of antiviral agents targeting flavivirus envelope proteins
Li, Ze,Khaliq, Mansoora,Zhou, Zhigang,Post, Carol Beth,Kuhn, Richard J.,Cushman, Mark
scheme or table, p. 4660 - 4671 (2009/07/11)
Flavivirus envelope proteins (E proteins) have been shown to play a pivotal role in virus assembly, morphogenesis, and infection of host cells. Inhibition of flavivirus infection of a host cell by means of a small molecule envelope protein antagonist is an attractive strategy for the development of antiviral agents. Virtual screening of the NCI chemical database using the dengue virus envelope protein structure revealed several hypothetical hit compounds. Bioassay results identified a class of thiazole compounds with antiviral potency in cell-based assays. Modification of these lead compounds led to a series of analogues with improved antiviral activity and decreased cytotoxicity. The most active compounds 11 and 36 were effective in the low micromolar concentration range in a cellular assay system.
NOVEL 2-ARYLTHIAZOLE COMPOUNDS AS PPARALPHA AND PPARGAMA AGONISTS
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Page 85-86, (2010/02/06)
The present invention relates to compounds of formula (I) wherein Rl to R10, X, Y and n are as defined in the description and claims, and pharmaceutically acceptable salts and esters thereof. The compounds are useful for the treatment of diseases such as diabetes.
