833-39-6Relevant academic research and scientific papers
Discovery of new benzhydrol biscarbonate esters as potent and selective apoptosis inducers of human melanomas bearing the activated ERK pathway: SAR studies on an ERK MAPK signaling modulator, ACA-28
Satoh, Ryosuke,Hamada, Naoya,Yamada, Ami,Kanda, Yuki,Ishikawa, Fumihiro,Takasaki, Teruaki,Tanabe, Genzoh,Sugiura, Reiko
, (2020/08/06)
The recent discovery that an ERK signaling modulator [ACA-28 (2a)] preferentially kills human melanoma cell lines by inducing ERK-dependent apoptosis has generated significant interest in the field of anti-cancer therapy. In the first SAR study on 2a, here, we successfully developed candidates (2b, 2c) both of which induce more potent and selective apoptosis towards ERK-active melanoma cells than 2a, thus revealing the structural basis for inducing the ERK-dependent apoptosis and proposing the therapeutic prospect of these candidates against ERK-dependent cancers represented by melanoma.
Visible-Light-Triggered C-C and C-N Bond Formation by C-S Bond Cleavage of Benzylic Thioethers
Lanzi, Matteo,Merad, Jérémy,Boyarskaya, Dina V.,Maestri, Giovanni,Allain, Clémence,Masson, Géraldine
supporting information, p. 5247 - 5250 (2018/09/13)
The cleavage of sulfidic C-S bonds under visible-light irradiation was harnessed to generate carbocations under neutral conditions and synthesize valuable di- and triarylalkanes as well as benzyl amines. To this end, photoredox catalysis and direct photoinduced C-S bond cleavage are used as complementary approaches and participate in the versatility of the general strategy. Extensive mechanistic studies have demonstrated the diversity of the reaction mechanism at work in these different reactions.
Chiral phosphoric acid catalyzed asymmetric addition of naphthols to para -quinone methides
Wong, Yuk Fai,Wang, Zhaobin,Sun, Jianwei
supporting information, p. 5751 - 5754 (2016/07/06)
An asymmetric addition of naphthols to in situ generated para-quinone methides catalyzed by a chiral phosphoric acid is described. A range of useful triarylmethanes can be generated from stable general para-hydroxybenzyl alcohols with good efficiency and enantioselectivity.
A general Br?nsted acid-catalyzed allylation of benzhydryl alcohols
Orizu, Ifedi,Bolshan, Yuri
supporting information, p. 5798 - 5800 (2016/12/03)
Efficient Br?nsted acid-catalyzed allylation of benzhydryl alcohols has been developed. The reaction occurs within 5?min in the presence of sub-stoichiometric amounts of HBF4·OEt2to afford the desired products in good to excellent yields. A variety of functional groups were tolerated under the developed conditions including amides, aldehydes, hydroxyl and carboxylic acid.
Br?nsted Acid-Catalyzed Reactions of Trifluoroborate Salts with Benzhydryl Alcohols
Fisher, Kayla M.,Bolshan, Yuri
, p. 12676 - 12685 (2016/01/09)
Br?nsted acid-catalyzed carbon-carbon bond forming methodology using potassium alkynyl- and alkenyltrifluoroborate salts has been developed. Organotrifluoroborates react with benzhydryl alcohols to afford a broad range of alkynes and alkenes in good to excellent yields. This protocol features good atom economy because organotrifluoroborate salts and alcohols react in a 1:1 ratio. Furthermore, a variety of unprotected functional groups were tolerated under the developed conditions, including amide, aldehyde, free hydroxyl, and carboxylic acid.
Direct electrosynthesis of ketones from benzylic methylenes by electrooxidative C-H activation
Meng, Li,Su, Jihu,Zha, Zhenggen,Zhang, Li,Zhang, Zhenlei,Wang, Zhiyong
supporting information, p. 5542 - 5545 (2013/05/23)
Electrify your chemistry! Direct electrosynthesis of ketones from benzylic methylenes in an undivided cell was realized in moderate to good yields (see scheme). In this electrosynthesis, electrons instead of conventional oxidants and catalysts are employed to make the reaction environmentally benign. Moreover, the reaction intermediate radical was detected by ESR spectroscopy and the reaction mechanism was clarified.
Synthesis of fluorenone derivatives through Pd-catalyzed dehydrogenative cyclization
Li, Hu,Zhu, Ru-Yi,Shi, Wen-Juan,He, Ke-Han,Shi, Zhang-Jie
supporting information, p. 4850 - 4853,4 (2012/12/12)
Palladium-catalyzed dual C-H functionalization of benzophenones to form fluorenones by oxidative dehydrogenative cyclization is reported. This method provides a concise and effective route toward the synthesis of fluorenone derivatives, which shows outstanding functional group compatibility.
Palladium catalyzed isomerization of alkenes: A pronounced influence of an o-phenol hydroxyl group
Fan, Jinmin,Wan, Changfeng,Wang, Qiang,Gao, Linfeng,Zheng, Xiaoqi,Wang, Zhiyong
supporting information; experimental part, p. 3168 - 3172 (2011/02/25)
A novel palladium catalyzed isomerization of alkenes has been found, where an ortho-phenol hydroxyl group has a pronounced influence on the isomerization.
A metal-free catalytic system for the oxidation of benzylic methylenes and primary amines under solvent-free conditions
Zhang, Jintang,Wang, Zhentao,Wang, Ye,Wan, Changfeng,Zheng, Xiaoqi,Wang, Zhiyong
supporting information; scheme or table, p. 1973 - 1978 (2010/06/15)
Iodine-pyridine-tert-butylhydroperoxide is developed as a green and efficient catalytic system for the oxidation of benzylic methylenes to ketones and primary amines to nitriles. The reaction conditions are quite mild and environmentally benign, no transition metals, organic solvents or hazard reagents being needed. The oxidation of benzylic methylenes gave the corresponding ketones in excellent yields with complete chemoselectivity, while the oxidation of primary amines was complete in several minutes, affording various nitriles in moderate to good yields.
Acetoxybenzhydrols as highly active and stable analogues of 1′S-1′-acetoxychavicol, a potent antiallergic principal from Alpinia galanga
Yasuhara, Tomohisa,Manse, Yoshiaki,Morimoto, Takayuki,Qilong, Wang,Matsuda, Hisashi,Yoshikawa, Masayuki,Muraoka, Osamu
scheme or table, p. 2944 - 2946 (2010/01/16)
Through SAR studies on 1′S-1′-acetoxychavicol acetate (1) against Type I antiallergic activity by indexing release of β-hexosaminidase, a marker of antigen-IgE-mediated degranulation in RBL-2H3 cells, more stable and potent analogue, 4-(methoxycarbonyloxy
