25236-63-9Relevant academic research and scientific papers
Novel leucine ureido derivatives as aminopeptidase N inhibitors using click chemistry
Cao, Jiangying,Ma, Chunhua,Zang, Jie,Gao, Shuai,Gao, Qianwen,Kong, Xiujie,Yan, Yugang,Liang, Xuewu,Ding, Qin'ge,Zhao, Chunlong,Wang, Binghe,Xu, Wenfang,Zhang, Yingjie
, p. 3145 - 3157 (2018/06/01)
The over-expression of aminopeptidase N on diverse malignant cells is associated with the tumor angiogenesis and metastasis. In this report, one new series of leucine ureido derivatives containing the triazole moiety was designed, synthesized and evaluated as APN inhibitors. Among them, compound 13v showed the best APN inhibition with an IC50 value of 0.089 ± 0.007 μM, which was two orders of magnitude lower than that of bestatin (IC50 = 9.4 ± 0.5 μM). Compound 13v also showed dose-dependent anti-angiogenesis activities. Even at the lower concentration (10 μM), compound 13v presented similar anti-angiogenesis activity compared with bestatin at 100 μM in both the human umbilical vein endothelial cells (HUVECs) capillary tube formation assay and the rat thoracic aorta rings test. Moreover, compared with bestatin, 13v exhibited comparable, if not better in vivo anti-metastasis activity in a mouse H22 pulmonary metastasis model.
Cobalt-Catalyzed Formation of Functionalized Diarylmethanes from Benzylmesylates and Aryl Halides
Reddy, Bhoomireddy Rajendra Prasad,Chowdhury, Sushobhan,Auffrant, Audrey,Gosmini, Corinne
supporting information, p. 3026 - 3029 (2018/08/24)
A simple cobalt-catalyzed reductive coupling protocol allowing the synthesis of functionalized diarylmethanes from benzyl mesylate is described. The possibility to directly use the benzyl alcohol as a result of a two-step reaction is also presented. This method tolerates a variety of functional groups. A benzyl radical is likely involved. (Figure presented.).
Nickel/bis(oxazoline)-catalyzed asymmetric negishi arylations of racemic secondary benzylic electrophiles to generate enantioenriched 1,1-diarylalkanes
Do, Hien-Quang,Chandrashekar,Fu, Gregory C.
supporting information, p. 16288 - 16291 (2013/12/04)
A tertiary stereogenic center that bears two different aryl substituents is found in a variety of bioactive compounds, including medicines such as Zoloft and Detrol. We have developed an efficient method for the synthesis of enantioenriched 1,1-diarylalkanes from readily available racemic benzylic alcohols. Formation of a benzylic mesylate (which is not isolated), followed by treatment with an arylzinc reagent, LiI, and a chiral nickel/bis(oxazoline) catalyst, furnishes the Negishi cross-coupling product in high ee and good yield. A wide array of functional groups (e.g., an aryl iodide, a thiophene, and an N-Boc-indole) are compatible with the mild reaction conditions. This method has been applied to a gram-scale synthesis of a precursor to Zoloft.
Chemoenzymatic approaches to obtain chiral-centered selenium compounds
Brondani, Patricia B.,Guilmoto, Nathalie M. A. F.,Andrade, Leandro H.,Dudek, Hanna M.,Fraaije, Marco W.
, p. 10431 - 10436,6 (2012/12/12)
The synthesis of chiral-centered selenium compounds is presented. Enantioselective oxidations of these organoselenium compounds were performed using a wide range of biocatalysts, including Baeyer-Villiger monooxygenases, oxidoreductases-containing Aspergillus terreus and lipase (Cal-B) in the presence of oxidants. Finally, efficient synthesis of enantiopure organoselenium compounds using a kinetic resolution approach mediated by Cal-B was achieved.
Chemoenzymatic approaches to obtain chiral-centered selenium compounds
Brondani, Patrícia B.,Guilmoto, Nathalie M.A.F.,Dudek, Hanna M.,Fraaije, Marco W.,Andrade, Leandro H.
, p. 10431 - 10436 (2013/01/15)
The synthesis of chiral-centered selenium compounds is presented. Enantioselective oxidations of these organoselenium compounds were performed using a wide range of biocatalysts, including Baeyer-Villiger monooxygenases, oxidoreductases-containing Aspergillus terreus and lipase (Cal-B) in the presence of oxidants. Finally, efficient synthesis of enantiopure organoselenium compounds using a kinetic resolution approach mediated by Cal-B was achieved.
A Lewis acid mediated schmidt reaction of benzylic azide: Synthesis of sterically crowded aromatic tertiary amines
Murali, Annamalai,Puppala, Manohar,Varghese, Babu,Baskaran, Sundarababu
supporting information; experimental part, p. 5297 - 5302 (2011/11/12)
An efficient one-pot synthesis of sterically hindered aromatic tertiary amines through Lewis acid induced intermolecular Schmidt reaction of benzylic azides is described. In the presence of EtAlCl2, benzylic azide underwent a smooth Schmidt reaction to give the corresponding iminium ion, which, upon reduction with NaBH4 in situ, afforded the tertiary amine. The effects of substituents on the aromatic ring and the steric effects of the alkyl side chain have also been studied.
