- Identification of novel 2-((1-(benzyl(2-hydroxy-2-phenylethyl)amino)-1-oxo- 3-phenylpropan-2-yl)carbamoyl)benzoic acid analogues as BMP-2 stimulators
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The synthesis and SAR studies of 10 new chemical entities (NCEs) that have shown BMP-2 stimulation and osteoblast differentiation are reported. Among these, 2-((1-(benzyl(2-hydroxy-2-phenylethyl)amino)-1-oxo-3-phenylpropan-2-yl) carbamoyl)benzoic acid (11) was the most effective while its analogue 13 also showed good activity in inducing osteoblast BMP-2 production. Compound 11 induced osteoblast differentiation in vitro, and this effect was abrogated by a physiological BMP-2 inhibitor, noggin. It also exhibited dose dependent increase in nascent bone formation (2.16- and 3.12-fold more than the control at 1 and 5 mg/kg dose, respectively) at the fracture site in rats. At the maximum osteogenic concentration, compound 11 significantly inhibited osteoblastic proteosomal activity. This compound was safe, as it had no effect on BMP synthesis in cardiovascular tissue.
- Balaramnavar, Vishal M.,Khan, Imran A.,Siddiqui, Jawed Akhtar,Khan, Mohd Parvez,Chakravarti, Bandana,Sharan, Kunal,Swarnkar, Gaurav,Rastogi, Namrata,Siddiqui,Mishra, Durga Prasad,Chattopadhyay, Naibedya,Saxena, Anil K.
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p. 8248 - 8259
(2013/01/15)
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- Synthesis and 2D QSAR of O-sulphonated β-aminols derivatives as novel antifungal and antibacterial agents
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Synthesis of a series of b-aminol derivatives using regioselective opening reaction catalyzed by SiO2 (60-120 mesh) and O-sulphonation in THF-KOH system, comprising tert-butoxycarbonyl at secondary nitrogen and evaluate for various stains of bacteria and fungi. SAR study of synthesized compound using backward regression analysis.
- Saxena, Anil K.,Sharma, Sugandha,Pandey, Atindra K.,Shukla, Praveen K.
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supporting information; experimental part
p. 6476 - 6481
(2011/11/29)
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- Weinreb amide based synthetic equivalents for convenient access to 4-aryl-1,2,3,4-tetrahydroisoquinolines
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New synthetic equivalents, N-methoxy-N-methyl-N′-phenylsulfonyl glycinamide and N-methoxy-N-methyl-N′-benzyl-N′-tert-butyloxy carbonyl glycinamide based on WA functionality were developed for the convenient synthesis of 4-aryl-1,2,3,4-tetrahydroisoquinoline framework. Two simple reactions, N-benzylation and addition of arylmagnesium halide on the WA functionality of the former afforded the key intermediate for convenient synthesis of N-phenylsulfonyl protected 4-aryl-1,2,3,4-tetrahydroisoquinoline, through reduction and acid promoted cyclization. With the latter, the addition of arylmagnesium halide on the WA functionality followed by the same protocol afforded the direct synthesis of 4-aryl-1,2,3,4-tetrahydroisoquinolines in good yields. The acid promoted cyclization step enabled concomitant removal of N-Boc protection.
- Kommidi, Harikrishna,Balasubramaniam, Sivaraman,Aidhen, Indrapal Singh
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experimental part
p. 3723 - 3729
(2010/07/05)
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- Enantioselective synthesis of β-hydroxy amines and aziridines using asymmetric transfer hydrogenation of α-amino ketones
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Enantioselective transfer hydrogenation of α-amino ketones is an effective method for the asymmetric synthesis of β-hydroxy amines and aziridines.
- Kawamoto,Wills
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p. 1916 - 1928
(2007/10/03)
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- Stereocontrol between remote atom centers in acyclic substrates. Anti addition of hydride to 1,5-, 1,6-, and 1,7-hydroxy ketones
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For conformationally unconstrained, acyclic organic compounds, the control of stereogenic centers at remote positions of a chain, that is, at a distance of four or more atom centers, remains a challenging problem in asymmetric synthesis. We report on our
- Zhang, Han-Cheng,Harris, Bruce D.,Costanzo, Michael J.,Lawson, Edward C.,Maryanoff, Cynthia A.,Maryanoff, Bruce E.
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p. 7964 - 7981
(2007/10/03)
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