- A STEREOISOMERICALLY PURE NK-3 RECEPTOR ANTAGONIST AND CRYSTALLINE FORMS THEREOF
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A stereoisomerically pure NK-3 receptor antagonist is provided, including crystalline free base and salt forms thereof, as well as pharmaceutical compositions comprising the same. Also provided are methods for production of the stereoisomerically pure NK-
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Page/Page column 29-30
(2021/02/19)
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- Copper-Photocatalyzed Contra-Thermodynamic Isomerization of Polarized Alkenes
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The contra-thermodynamic isomerization of α- and β-substituted cinnamate derivatives catalyzed by the Cu(OAc)2/rac-BINAP complex under blue light irradiation is reported. The use of an oxazolidinone template, which favored the complexation of the copper catalyst to the substrate, allowed the E → Z isomerization of the catalytically formed chromophore under simple and robust reaction conditions in good to excellent ratios. The mechanism of this process based on the transient formation of a chromophore was also studied.
- Bouillon, Jean-Philippe,Brégent, Thibaud,Poisson, Thomas
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p. 7688 - 7693
(2020/10/09)
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- Synthesis and SAR study of modulators inhibiting tRXRα-dependent AKT activation
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RXRα represents an intriguing and unique target for pharmacologic interventions. We recently showed that Sulindac and a designed analog could bind to RXRα and modulate its biological activity, including inhibition of the interaction of an N-terminally truncated RXRα (tRXRα) with the p85α regulatory subunit of phosphatidylinositol-3-OH kinase (PI3K). Here we report the synthesis, testing and SAR of a series of novel analogs of Sulindac as potential modulators for inhibiting tRXRα-dependent AKT activation. A new compound 30 was identified to have improved biological activity.
- Wang, Zhi-Gang,Chen, Liqun,Chen, Jiebo,Zheng, Jian-Feng,Gao, Weiwei,Zeng, Zhiping,Zhou, Hu,Zhang, Xiao-Kun,Huang, Pei-Qiang,Su, Ying
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p. 632 - 648
(2013/05/09)
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- Microwave-assisted synthesis of the (E)-α-methylalkenoate framework from multifunctionalized allylic phosphonium salts
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A convenient and general microwave-assisted method for the synthesis of stereochemically defined α-methylalkenoic acids and esters from allylic phosphonium salts in a basic aqueous medium is described. A selective preparation of acids or esters was dependent on the base (NaOH or NaHCO 3) employed in the reaction and could be achieved with good to excellent yields under mild conditions in the absence of hydrides and reducing agents.
- Meier, Lidiane,Ferreira, Misael,Sa, Marcus M.
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p. 179 - 186
(2012/07/14)
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- Synthetic applications of Baylis-Hillman chemistry: An efficient and solely stereoselective synthesis of (E)-α-methylcinnamic acids and potent hypolipidemic agent LK-903 from unmodified Baylis-Hillman adducts
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An efficient and solely stereoselective synthesis of (E)-α- methylcinnamic acids has been accomplished in single pot by reduction of the unmodified Baylis-Hillman adducts, methyl-3-hydroxy-3-aryl-2- methylenepropanoates with I2/NaBH4 reagent system at room temperature followed by hydrolysis. The efficacy of this method has been proved in the total synthesis of 1-[p-(myristyloxy)-α-methylcinnamoyl]glycerol, LK-903, a highly active hypolipidemic agent.
- Das, Biswanath,Banerjee, Joydeep,Chowdhury, Nikhil,Majhi, Anjoy
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p. 1725 - 1727
(2007/10/03)
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- A facile one-pot stereoselective synthesis of trisubstituted (E)-2-methylalk-2-enoic acids from unactivated Baylis-Hillman adducts and a simple access to some important insect pheromones
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An efficient one-pot stereoselective synthesis of trisubstituted (E)-2-methylalk-2-enoic acids has been accomplished by treatment of unactivated Baylis-Hillman adducts, 3-hydroxy-2-methylenealkanoates, with Al-NiCl2·6H2O in methanol at room temperature followed by hydrolysis. The method has been applied to the synthesis of three important insect pheromones, (4S,2E)-2,4-dimethyl-2-hexenoic acid, (+)-(S)-manicone and (+)-(S)-normanicone.
- Das, Biswanath,Chowdhury, Nikhil,Banerjee, Joydeep,Majhi, Anjoy
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p. 6615 - 6618
(2007/10/03)
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- Nitrogen ligands: The transition metal catalyzed reaction of aryl halides with olefins (Mizoroki-Heck), phenylboronic acid (Suzuki coupling) and Buchwald-Hartwig amination, new catalysts and effect of co-catalysts - Aryl halide activation - Part I
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Nitrogen ligands are an excellent alternative for the traditional P-ligands in the Pd catalyzed Mizoroki-Heck reaction, Suzuki coupling and Buchwald-Hartwig aryl amination. Pd complexes of dimethyl glyoxime, 8-hydroxyquinoline, salen, picolinic acid, and DAB ligands gave high yields of the E-cinnamates and E-stilbenes from aryl iodides. Acetophenone oxime N, N-dimethybenzylamine and ferrocenyl oxime palladacycle are better catalysts with comparable yields, high TON (95, 000) and TOF's (2, 500 h-1) to P-ligand catalysts. Aryl bromides and in a few cases, aryl chlorides could also be activated by these complexes by the use of Lewis acid and (C 4H9)4NI as additives. Cy-DAB ligands gave good yields with electron rich aryl bromides and the use of ionic liquid improve the yield. These N-ligand metal complexes can be readily synthesized and the ligands possess the advantage of easy functional group modifications and convenient synthetic methods compared to P-ligands. The degradation reactions associated with P-ligands are not observed in the N-ligands, with comparable, high thermal, moisture and air stability and insensitivity. Activation of aryl bromides (Mizoroki-Heck reaction, Suzuki reaction) could be achieved in high yields, TON and TOF (86-94% yield, TON: 36, 000-90, 000, TOF: 6, 000-11, 500 h-1) catalyzed by monomeric amine and oxime palladacycles (Cat-8, 11, 13 B) with a N-heterocyclic carbene ligand better than a phosphorous ligand. Molten (C 4H9)4NBr is an efficient ionic liquid medium for the Mizoroki-Heck reaction of aryl bromides, giving higher yields. Low to moderate yields of aryl amination are obtained with the carbene palladacycle and N, N-dibenzyl piperazine Pd complexes.
- Iyer, Suresh,Kulkarni, Girish M.,Ramesh,Sattar, Aruna K.
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p. 1894 - 1908
(2007/10/03)
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- A facile synthesis of 2-benzyloxy/2-(4-isopropylbenzyloxy)-2-methyl-3-(4- substituted phenyl)propanoic acid based insulin sensitizing agents: RSR 13-15 and PKR13-15
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The title compounds (RSR13-15) and (PKR13-15) were prepared by the etherification of benzyl alcohol and 4-isopropylbenzyl alcohol respectively with ethyl-2-bromo-2-methyl-3-(4-substituted phenyl)propanoates in the presence of sodium hydride in THF followed by alkaline hydrolysis of the ethyl esters. The substituted propanoic acids used in this synthetic sequence were prepared by magnesium-methanol reduction of correspondingly substituted propenoic acids, which in turn were prepared via 'Perkin Reaction' of 4-substituted benzaldehydes with propanoic anhydride. The details of the synthetic sequence followed for the preparation of all these compounds having almost all the structural features required for a compound to act as a potent insulin sensitizing agent are reported. Birkhaeuser Boston 2004.
- Verma, Raman K.,Singla, Rubina,Punniyakoti
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p. 660 - 676
(2007/10/03)
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- A facile one-pot conversion of acetates of the Baylis-Hillman adducts to [E]-α-methylcinnamic acids
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A simple and convenient stereoselective synthesis of [E]-α- methylcinnamic acids via the nucleophilic addition of hydride ion from sodium borohydride to methyl 3-acetoxy-3-aryl-2-methylenepropanoates followed by hydrolysis and crystallization is described
- Basavaiah,Krishnamacharyulu,Hyma,Sarma,Kumaragurubaran
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p. 1197 - 1200
(2007/10/03)
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