136329-29-8Relevant articles and documents
Synthesis of Versatile Intermediates for Cyclopentanoid Natural Products via Enantioselective Deprotonation of Substituted Cyclopentene Oxide
Bhuniya, Debnath,Gupta, Arpita Datta,Singh, Vinod K.
, p. 2847 - 2850 (1995)
Enantioselective deprotonation of cis and trans-3,4-epoxycyclopentan-1-ol derivatives with phenylglycine based ligand (R)-5 was studied.The cyclopentanoid intermediates were obtained in a maximum of 88percent ee.
Effective asymmetric Michael addition of anthrone to nitroalkenes using chiral tetraoxacalix[2]arene[2]triazines as organocatalysts
Genc, Hayriye Nevin
, p. 711 - 718 (2019/07/16)
Novel chiral secondary amines bearing a tetraoxacalix[2]arene[2]triazine scaffold were created and used for catalytic asymmetric Michael reaction of anthrone with nitroalkenes. The relevant adducts were obtained in good to excellent yields (82%-98%) and enantioselectivities (75%-98%).
SUBSTITUTED HETEROCYCLIC ACETAMIDES AS KAPPA OPIOID RECEPTOR (KOR) AGONISTS
-
Page/Page column 124, (2013/09/26)
The present invention relates to a series of substituted compounds having the general formula (I), including their ste reoisomers and/or their pharmaceutically acceptable salts, wherein R1, R2, R3. R4, R5, and R6 are as defined herein. This invention also relates to methods of making these compounds including intermediates. The compounds of this invention are effective at the kappa (κ) opioid receptor (KOR) site. Therefore, the compounds of this invention are useful as pharmaceutical agents, especially in the treatment and/or prevention of a variety of central nervous system disorders (CNS), including but not limited to acute and chronic pain, and associated disorders, particularly functioning peripherally at the CNS.
Synthesis and application of L-proline and R-phenylglycine derived organocatalysts for direct asymmetric Michael addition of cyclohexanone to nitroalkenes
Naziroglu, Hayriye Nevin,Sirit, Abdulkadir
, p. 659 - 670 (2013/02/25)
Novel R-phenylglycine derived organocatalysts were prepared from the reaction of Cbz-R-phenylglycine with indoline, pyrrolidine, or (S)-(-)-2-(diphenylmethyl)pyrrolidine in 3 steps. The asymmetric Michael addition of cyclohexanone to nitroolefins was investigated using R-phenylglycine derivatives along with L-prolinamides as chiral catalysts. The desired products were obtained in excellent yields with enantioselectivities up to 90% ee and diastereomeric ratio up to 98:2 of the syn addition product. TUeBITAK, 2012.
Stereoselective reactions, 25. Enantioselective deprotonation of prochiral 4-substituted cyclohexanones by chiral chelated lithium amides
Shirai, Ryuichi,Sato, Daisaku,Aoki, Kazumasa,Tanaka, Masahide,Kawasaki, Hisashi,Koga, Kenji
, p. 5963 - 5972 (2007/10/03)
Enantioselective deprotonation of prochiral 4-substituted cyclohexanones (4a-d) by chiral chelated lithium amides (8a-k) in the presence of excess trimethylsilyl chloride was realized to give the corresponding chiral silyl enol ethers (6a-d) in up to 89% ee. It is shown that enantioselectivity of the reaction is dependent on the solvent used, but becomes almost independent on the solvent in the presence of HMPA. The sense of asymmetric induction can be correlated to the configuration at the chiral carbon bearing amide nitrogen of the lithium amide.
Design, synthesis, and application of chiral nonracemic lithium amide bases in enantioselective deprotonation of epoxides
Bhuniya, Debnath,DattaGupta, Arpita,Singh, Vinod K.
, p. 6108 - 6113 (2007/10/03)
The reaction of epoxides with chiral nonracemic lithium amide bases, designed and prepared from (R)-phenylglycine, has been studied in detail. A maximum of 80% ee was obtained for conversion of cyclohexene oxide to (S)-2-cyclohexen-1-ol. Enantioselective deprotonation of a variety of other epoxides was studied. A cyclopentanoid core unit for prostaglandin synthesis was synthesized in 97% ee.
Enantioselective deprotonation of cyclohexene oxide to (R)-2-cyclohexen- 1-ol
Bhuniya,Singh
, p. 1475 - 1481 (2007/10/02)
The reaction of cyclohexene oxide with homochiral lithium amides, prepared from (S)-phenylglycine and (S)-valine has been studied and (R)-2-cyclohexen- 1-ol 3 was prepared in a maximum of 72% ee. The optical purity was determined by 1H NMR measurement of the α-methoxy-α-(trifluoromethyl)phenyl acetic acid (MTPA) derivative of the corresponding alcohol.
Structure/Activity Studies Related to 2-(3,4-Dichlorophenyl)-N-methyl-N-acetamides: A Novel Series of Potent and Selective κ-Opioid Agonists
Barlow, Jeffrey J.,Blackburn, Thomas P.,Costello, Gerard F.,James, Roger,Count, David J. Le,et al.
, p. 3149 - 3158 (2007/10/02)
This paper describes the synthesis of a series of N-acetamides 1, variously substituted at the carbon adjacent to the amide nitrogen (C1), and related analogues, together with their biological evaluation as opioid κ agonists.In the first part of the study, the variants in N-acyl, N-alkyl, and amino functions were explored when the substituent at C1 was 1-methylethyl and the optimum was found to be exemplified by 2-(3,4-dichlorophenyl)-N-methyl-N-acetamide (13).Subsequently, racemic or chiral amino acids were used to introduce other alkyl and aryl substituents at C1 of the ethyl linking moiety.A series of potent compounds, bearing substituted-aryl groups at C1, were discovered, typified by 2-(3,4-dichlorophenyl)-N-methyl-N-acetamide (48), which was 5-fold more active as the racemate than 13 in vitro and exhibited potent naloxone-reversible analgesic effects (ED50 = 0.04 mg/kg sc) in a mouse abdominal constriction model.
