6956-41-8Relevant academic research and scientific papers
Microwave enhanced green synthesis of 2-pyrazolines, isoxazolines and cyclohexenones
Al-Bogami, Abdullah S.,Alkhathlan, Hamad Z.,Saleh, Tamer S.
, p. 6427 - 6433 (2013)
Hydroxy chalcones undergo simple cyclizations with phenylhydrazine to afford 2-pyrazolines under microwave irradiation in the presence of glacial AcOH as cyclizing agent, also undergo simple cyclizations with hydroxylamine to afford 2-isoxazolines under m
Unexpected ring opening of pyrazolines with activated alkynes: synthesis of 1H-pyrazole-4,5-dicarboxylates and chromenopyrazolecarboxylates
Bhimapaka, China Raju,Kolla, Sai Teja,Rayala, Nageswara Rao,Sridhar, Balasubramanian
supporting information, p. 334 - 338 (2022/01/20)
1H-Pyrazole-4,5-dicarboxylates and chromenopyrazole carboxylates were prepared by reacting pyrazolines with activated alkynes under neat conditions without a catalyst. The products were formed via unexpected ring opening of pyrazolines with the elimination of styrene/ethylene. These types of transformations are unknown and the products formed were confirmed using their spectral/analytical data. In addition, the structures of compounds 5e and 5n were confirmed by single-crystal X-ray analysis. Control experiments were conducted to support the proposed reaction mechanism.
TfOH mediated intermolecular electrocyclization for the synthesis of pyrazolines and its application in alkaloid synthesis
Annes, Sesuraj Babiola,Vairaprakash, Pothiappan,Ramesh, Subburethinam
, p. 30071 - 30075 (2018/09/11)
TfOH mediated easy access to interesting pyrazolines starting from an aldehyde, phenylhydrazine and styrene has been developed. The scope of this synthetic methodology has been explored by synthesizing various 1,3,5-trisubstituted pyrazolines in very good yields with very high regioselectivity. The origin of regioselectivity has been explained by comparing the stability of possible intermediate carbocations. The synthetic utility of a green solvent has been explored by synthesizing some of pyrazolines in a DES medium. The synthetic application of the present methodology is employed in the synthesis of a pyrazoline alkaloid.
Design, Synthesis, and Biological Evaluation of Pyrazoline-Based Hydroxamic Acid Derivatives as Aminopeptidase N (APN) Inhibitors
Cao, Jiangying,Zang, Jie,Ma, Chunhua,Li, Xiaoguang,Hou, Jinning,Li, Jin,Huang, Yongxue,Xu, Wenfang,Wang, Binghe,Zhang, Yingjie
, p. 431 - 436 (2018/02/21)
Aminopeptidase N (APN) has been recognized as a target for anticancer treatment due to its overexpression on diverse malignant tumor cells and association with cancer invasion, metastasis and angiogenesis. Herein we describe the synthesis, biological evaluation, and structure–activity relationship study of two new series of pyrazoline analogues as APN inhibitors. Among these compounds, 5-(2-(2-(hydroxyamino)-2-oxoethoxy)phenyl)-3-phenyl-4,5-dihydro-1H-pyrazole-1-carboxamide (compound 13 e) showed the best APN inhibition with an IC50 value of 0.16±0.02 μm, which is more than one order of magnitude lower than that of bestatin (IC50=9.4±0.5 μm). Moreover, compound 13 e was found to inhibit the proliferation of diverse carcinoma cells and to show potent anti-angiogenesis activity. At the same concentration, compound 13 e presents significantly higher anti-angiogenesis activity than bestatin in human umbilical vein endothelial cells (HUVECs) capillary tube formation assays. The putative binding mode of 13 e in the active site of APN is also discussed.
A novel methodology for synthesis of dihydropyrazole derivatives as potential anticancer agents
Wang, Xu,Pan, Ying-Ming,Huang, Xiao-Chao,Mao, Zhong-Yuan,Wang, Heng-Shan
supporting information, p. 2028 - 2032 (2014/03/21)
A novel, simple, and efficient method for the synthesis of 4,5-dihydropyrazole derivatives has been developed. The reaction proceeded through the base-induced isomerization of easily accessible propargyl alcohols followed by cyclization of α,β-unsaturated hydrazones. Furthermore, selected compounds 3ab and 3ac exhibited good activities against Bel-7404 (human hepatoma cancer), HepG2 (human liver cancer), NCI-H460 (human lung cancer) and SKOV3 (human ovarian cancer) cell lines with IC50 in the range of 22-46 μmol L-1.
Synthesis of pyrazoline and isoxazoline in triethanolamine medium
Agrawal, Nitin N.,Soni
, p. 2700 - 2701 (2007/10/03)
Reactions of chalcones 1a-u with phenylhydrazine and hydrazine hydrate give pyrazolines 2a-u and with hydroxylamine hydrochloride yield isoxazolines 3a-c in triethanolamine medium. The structures of products are established by melting points, chemical studies and spectral data (IR and 1HNMR).
SYNTHESIS OF SOME ISOMERIC PYRAZOLES
Sharma, T. C.,Pawar, S. R.,Reddy, N. J.
, p. 159 - 162 (2007/10/02)
The syntheses of 3-o-hydroxyphenyl-1,5-diphenylpyrazoles (III) and 1,3-diphenyl-5-o-hydroxyphenylpyrazoles (V) by the oxidation of corresponding pyrazolines (II) with manganese dioxide and by the reaction of phenylhydrazine with 2'-hydroxychalcone dibromi
Action of Phenylhydrazine Hydrochloride on Chalkone Dibromides in Dimethylformamide
Joshi, M. G.,Wadodkar, K. N.
, p. 1090 - 1092 (2007/10/02)
Chalkone dibromides (II) when treated with phenylhydrazine hydrochloride in DMF do not give the expected pyrazoles, but afford 3,5-diaryl-1-phenylpyrazolines (III) which are the normal products of chalkones (I) and phenylhydrazine hydrochloride in DMF.
