18808-85-0Relevant academic research and scientific papers
Ionic liquid-mediated facile synthesis of novel spiroheterobicyclic rings as potential antifungal and antibacterial drugs
Dandia, Anshu,Jain, Anuj K.
, p. 104 - 113 (2013)
A pseudo four-component reaction of urea or thiourea, diverse aryl aldehydes, and 3-methyl-1-phenyl-2-pyrazolin-5-one in ionic liquids yields novel azaspiro[4.5]decene derivatives. However, the corresponding reaction in volatile organic solvents gives Kno
A three-component, general and practical route for diastereoselective synthesis of aza-spirocyclic pyrazolonesviaa decarboxylative annulation process
Awasthi, Annapurna,Yadav, Pushpendra,Tiwari, Dharmendra Kumar
, p. 2374 - 2383 (2021/02/16)
An efficient, general, and practical route for highly diastereoselective synthesis of aza-spirocyclic pyrazolones from easily available α-amino acids, aldehydes, and alkylidene pyrazolones by means of a decarboxylative annulation process is reported. This
Enantioselective Synthesis of Spiropyrazolone-Fused Cyclopenta[ c]chromen-4-ones Bearing Five Contiguous Stereocenters via (3+2) Cycloaddition
Khairnar, Pankaj V.,Su, Yin-Hsiang,Edukondalu, Athukuri,Lin, Wenwei
, p. 12326 - 12335 (2021/08/24)
An enantioselective synthesis of spiropyrazolone-fused cyclopenta[c]chromen-4-ones is demonstrated via a (3+2) cycloaddition reaction. The reactions of 3-homoacylcoumarins and α,β-unsaturated pyrazolones in the presence of the cinchona-alkaloid derived hy
Discovery of novel inhibitors of human phosphoglycerate dehydrogenase by activity-directed combinatorial chemical synthesis strategy
Gou, Kun,Luo, Youfu,Luo, Yuan,Sun, Qingxiang,Tan, Yuping,Tao, Lei,Zhao, Yinglan,Zhou, Xia,Zhou, Yue,Zuo, Zeping
supporting information, (2021/07/26)
Serine, the source of the one-carbon units essential for de novo purine and deoxythymidine synthesis plays a crucial role in the growth of cancer cells. Phosphoglycerate dehydrogenase (PHGDH) which catalyzes the first, rate-limiting step in de novo serine biosynthesis has become a promising target for the cancer treatment. Here we identified H-G6 as a potential PHGDH inhibitor from the screening of an in-house small molecule library based on the enzymatic assay. We adopted activity-directed combinatorial chemical synthesis strategy to optimize this hit compound. Compound b36 was found to be the noncompetitive and the most promising one with IC50 values of 5.96 ± 0.61 μM against PHGDH. Compound b36 inhibited the proliferation of human breast cancer and ovarian cancer cells, reduced intracellular serine synthesis, damaged DNA synthesis, and induced cell cycle arrest. Collectively, our results suggest that b36 is a novel PHGDH inhibitor, which could be a promising modulator to reprogram the serine synthesis pathway and might be a potential anticancer lead worth further exploration.
Enantio- and Diastereoselective Synthesis of β-Aryl-β-pyrazolyl α-Amino Acid Esters via Copper-Catalyzed Reaction of Azomethine Ylides with Benzylidenepyrazolones
Gong, Yan-Chuan,Wang, Yue,Li, Er-Qing,Cui, Hao,Duan, Zheng
supporting information, (2019/02/07)
A fully stereoselective synthesis of unnatural chiral β-aryl-β-pyrazolyl α-amino acid esters via copper-catalyzed addition reactions of azomethine ylides with benzylidenepyrazolones bearing two contiguous stereogenic centers was developed. A 1H-pyrazol-5-ol was introduced by the aromatization of 3H-pyrazol-3-one in the reaction. The transformation operated at room temperature and afforded β-1H-pyrazol-5-ol-α-amino esters in high yields with good to excellent levels of diastereo- and enantioselectivity.
Enantio- And diastereoselective synthesis of b-Aryl-b-pyrazolyl a-amino acid esters via copper-catalyzed reaction of azomethine ylides with benzylidenepyrazolones
Gong, Yan-Chuan,Wang, Yue,Li, Er-Qing,Cui, Hao,Duan, Zheng
supporting information, p. 1389 - 1393 (2019/10/28)
A fully stereoselective synthesis of unnatural chiral b-aryl-b-pyrazolyl a-amino acid esters via copper-catalyzed addition reactions of azomethine ylides with benzylidenepyrazolones bearing two contiguous stereogenic centers was developed. A 1H-pyrazol-5-ol was introduced by the aromatization of 3H-pyrazol-3-one in the reaction. The transformation operated at room temperature and afforded b-1H-pyrazol-5-ol-a-amino esters in high yields with good to excellent levels of diastereo- and enantioselectivity.
Tosylmethylisocyanide (TosMIC) [3+2] cycloaddition reactions: A facile Van Leusen protocol for the synthesis of the new class of spirooxazolines, spiropyrrolines and Chromeno[3,4-c]pyrrols
Shaabani, Ahmad,Sepahvand, Heshmatollah,Bazgir, Ayoob,Khavasi, Hamid Reza
, p. 7058 - 7067 (2018/11/02)
The reactivity and chemo-, regio- and diastreo-selectivity of tosylmethyl isocyanides (TosMIC) are investigated in Van Leusen type [3 + 2] cycloaddition reactions with the various activate cyclic ketones and double C–C bonds in the synthesis of spirooxazolines, spiropyrrolines and chromeno[3,4-c]pyrrols in good to excellent yields under catalyst-free conditions without any activation at ambient temperature.
Lewis-Base-Catalyzed [1 + 2 + 2] Annulation Reaction of Morita-Baylis-Hillman Carbonates with Unsaturated Pyrazolones: Construction of All-Stereogenic Carbon Cyclopentane-Fused Dispiropyrazolones
Liang, Jin-Yan,Shen, Shou-Jie,Chai, Xiao-Qian,Lv, Ting
, p. 12744 - 12752 (2018/10/09)
The first Lewis-base-catalyzed unexpected [1 + 2 + 2] annulation reaction between Morita-Baylis-Hillman carbonates and unsaturated pyrazolones was developed. The multicyclic cyclopentane-fused dispiropyrazolone constructions containing five contiguous ste
Organocatalytic Asymmetric Michael/Hemiketalization/Retro-aldol Reaction of α-Nitroketones with Unsaturated Pyrazolones: Synthesis of 3-Acyloxy Pyrazoles
Maity, Rajendra,Gharui, Chandan,Sil, Arun K.,Pan, Subhas Chandra
supporting information, p. 662 - 665 (2017/02/10)
An organocatalytic asymmetric cascade Michael/hemiketalization/retro-aldol reaction between unsaturated pyrazolones and α-nitroketones is described. A bifunctional thiourea catalyst was found to be efficient for this reaction. With 10 mol % of catalyst, high yields as well as excellent enantioselectivities are attained for a variety of 3-acyloxy pyrazoles under mild reaction conditions.
Palladium N-heterocyclic carbene catalyzed expected and unexpected C-C and C-N functionalization reactions of 1-aryl-3-methyl-1: H -pyrazol-5(4 H)-ones
Purohit, Vishal B.,Karad, Sharad C.,Patel, Kirit H.,Raval, Dipak K.
, p. 111139 - 111143 (2016/12/07)
A palladium N-heterocyclic carbene [Pd(NHC)Cl2] complex of vitamin B1 developed earlier in our laboratory was successfully employed as an efficient catalyst for the regioselective C-C and C-N functionalization reactions of 1-aryl-3-methyl-1H-pyrazol-5(4H)-ones 1a-b. The catalyst was attempted for the C-H arylation, acylation and alkoxylation of 1a-b using the respective coupling substrates such as aryl iodides 2a-c, benzylic alcohols 3a-d and methanol/ethanol 4. It was surprisingly noted that the acylation and alkoxylation reactions underwent a diverse pathway to yield some unexpected products rather than the targeted ones. In the case of the arylation reactions only the targeted products have been observed. This has made the protocol very interesting compared to the conventional coupling reactions.
