cas 199942-74-0, (S)-1-N-Boc-piperidine-2-ethanol

Articles about 199942-74-0Total 16 be found

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(QUINOLINE OR ISOQUINOLINE)SULFONAMIDES OF CYCLIC AMINES AS ANTIPSYCHOTIC DRUGS
The invention relates to compounds of general formula (I) wherein: one of A1 and A2 represents a nitrogen atom and the other a carbon atom optionally substituted by halogen; the wave line between the sulfonamido moiety and B/C rings represents a single bond linking the sulfur atom to a non-bridgehead carbon atom, with the proviso that the part of ring C being detached by the dashed broken line is unsubstituted; n represents an integer from 0 to 3; Y represents a nitrogen or carbon atom; Z represents a 5-6 membered aromatic/ heteroaromatic ring optionally fused with a further aromatic or non- aromatic 5-6 membered heterocycle, the condensed ring system being linked via a non-bridgehead carbon atom. The compounds display high affinity for the D2, D3, 5-HT1A, 5-HT2A- 5-HT6 and 5-HT7 receptors and are useful for the treatment of psychotropic diseases or disorders associated with disturbances of the dopaminergic/ serotoninergic systems such as schizophrenia and autism.
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(2016/01/25)

A strategy for complex dimer formation when biomimicry fails: Total synthesis of ten coccinellid alkaloids
Although dimeric natural products can often be synthesized in the laboratory by directly merging advanced monomers, these approaches sometimes fail, leading instead to non-natural architectures via incorrect unions. Such a situation arose during our studies of the coccinellid alkaloids, when attempts to directly dimerize Natures presumed monomeric precursors in a putative biomimetic sequence afforded only a non-natural analogue through improper regiocontrol. Herein, we outline a unique strategy for dimer formation that obviates these difficulties, one which rapidly constructs the coccinellid dimers psylloborine A and isopsylloborine A through a terminating sequence of two reaction cascades that generate five bonds, five rings, and four stereocenters. In addition, a common synthetic intermediate is identified which allows for the rapid, asymmetric formal or complete total syntheses of eight monomeric members of the class.
Sherwood, Trevor C.,Trotta, Adam H.,Snyder, Scott A.
p. 9743 - 9753
(2014/07/22)

Enantioselective approach to quinolizidines: Total synthesis of cermizine D and formal syntheses of senepodine G and cermizine C
The formal syntheses of C5-epi-senepodine G and C 5-epi-cermizine C have been accomplished through a novel diastereoselective, intramolecular amide Michael addition process. The total synthesis of cermizine D has been achieved throug
Veerasamy, Nagarathanam,Carlson, Erik C.,Collett, Nathan D.,Saha, Mrinmoy,Carter, Rich G.
p. 4779 - 4800
(2013/06/27)

Asymmetric synthesis of (+)-vertine and (+)-lythrine
The total syntheses of the Lythracea alkaloids (+)-vertine and (+)-lythrine are described. Enantioenriched pelletierine is used as a chiral building block and engaged into a two step pelletierine condensation leading to two quinolizidin-2-one diastereomers in a 8:1 ratio. The major product is used in the synthesis of (+)-vertine via aryl-aryl coupling and ring closing metathesis to provide a Z-alkene α to the lactone carbonyl function. The same procedure was used for (+)-lythrine after base induced epimerization of the main quinolizidin-2-one diastereomer. Alternative classical ring closure strategies like macrolactonisation or aryl-aryl coupling failed.
Chausset-Boissarie, La?titia,àrvai, Roman,Cumming, Graham R.,Guénée, Laure,Kündig, E. Peter
supporting information; experimental part
p. 6473 - 6479
(2012/09/08)

Expedient enantioselective synthesis of cermizine D
An efficient enantioselective synthesis of cermizine D has been developed that exploits the use of a common intermediate to access over 85% of the carbon backbone. Key steps include an organocatalyzed heteroatom Michael addition, a diastereoselective alky
Veerasamy, Nagarathanam,Carlson, Erik C.,Carter, Rich G.
p. 1596 - 1599
(2012/06/05)

Enantioselective Synthesis of (+)-α-Conhydrine and (-)-Sedamine by L-ProlineCatalysed α-Aminooxylation
An efficient organocatalytic approach to the enantioslective synthesis of two important piperidine alkaloids, namely (+)α-conhydrine (98% ee) and (-)-sedamine (95 % ee), by L-pro-line-catalysed α-aminooxylation of aldehydes has been developed. The strategy involves an intramolecular cyclization to construct the piperidine core.
Shaikh, Tanveer Mahamadali,Sudalai, Arumugam
experimental part
p. 3437 - 3444
(2010/08/20)

Enantioselective organocatalytic intramolecular aza-Michael reaction: A concise synthesis of (+)-sedamine, (+)-allosedamine, and (+)-coniine
(Chemical Equation Presented) The intramolecular aza-Michael reaction of carbamates bearing remote α,β-unsaturated aldehydes under organocatalytic conditions took place with good yields and excellent ee's when Jorgensen catalyst IV was used in the process, giving rise to the enantioselective formation of several five- and six-membered heterocycles. The developed methodology was applied to the synthesis of three piperidine alkaloids.
Fustero, Santos,Jimenez, Diego,Moscardo, Javier,Catalan, Silvia,Del Pozo, Carlos
p. 5283 - 5286
(2008/09/18)

Efficient, asymmetric synthesis of (-)-isooncinotine
Asymmetric synthesis of (-)-isooncinotine, a 22-membered lactam of spermidine alkaloid, starting from resolution of 2-piperidineethanol with (S)-10-camphorsulfonic acid is reported. Michael addition, amidations, and aluminum hydride reduction were applied to form the moiety of spermidine. Retro-Michael addition was observed when β-amido- and β-amino-propionitriles were reduced by LAH. The effects of LAH versus AlH3 were discussed. The synthesis of the skeleton of this macrolide is achieved with ring-closing metathesis of the?diene prepared from acylation of the spermidine.
Cheng, Hsiu-Yi,Hou, Duen-Ren
p. 3000 - 3005
(2007/10/03)

THE S-ISOMER OF 2-{2-[N-(2-INDANYL)-N-PHENYLAMINO]ETHYL}PIPERIDINE AND OTHER DERMAL ANESTHETIC AGENTS
The present invention relates to the S-isomers of anesthetic compounds, the methods of treatment therewith, the compounds being useful for inducing local anesthesia, analgesia and sleep.
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(2010/10/20)

Synthesis by chiral diamine-mediated asymmetric alkylation
Chiral synthesis from an achiral starting material by chiral diamine-mediated, such as sparteine-mediated, intermolecular asymmetric alkylation with a strained cyclic ether in the presence of a Lewis acid.
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(2010/10/20)

Serine protease inhibitor
A serine protease inhibitor having the formula (I), in which J is H, R1, R1—O—C(O)—, R1—C(O—, R1—SO2—, R3OOC—(CHR2)p—, (R2a,R2b)N—CO—(CHR2)p— or Het-CO—(CHR2)p—;W is an amino-acid of the formula —NH—CHR1—C(O)—, —NR4—CH((CH2)qC(O)OR1)—C(O)—, —NR4—CH((CH2)qC(O)N(R2a,R2b))—C(O)—, —NR4—CH((CH2)qC(O)Het)-C(O)—, D-1-Tiq, D-3-Tiq, D-Atc, Aic, D-1-Piq, D-3 Piq, glutanyl or a (C1-C6) alkylester thereof;E is —NR2—CH2— or the fragment ?which is unsubstituted or substituted with (1-6C)alkyl, (1-6C)alkoxy or benzyloxy;R1 is selected form (1-12C)alkyl, (2-12C)alkenyl, (2-12C)alkynyl, (3-12C)cycloalkyl and (3-12C)cycloalkyl(1-6C)alkylene, which groups are unsubstituted or substituted with (3-12C)cycloalkyl, (1-6C)alkoxy, oxo, OH, CF3 or halogen, and from (6-14C)aryl, (7-15C)aralkyl, (8-16C)aralkenyl and (14-20C)(bisary)alkyl, wherein the aryl groups are unsubstituted or substituted with (1-6C)alkyl, (3-12C)cycloalkyl, (1-6C)alkoxy, OH, CF3 or halogen;R2, R2a and R2b are each independently selected from H, (1-C)alkyl, (3-8C)alkenyl, (3-8C)alkynyl, (3-8C)cycloalkyl and (3-6C)cycloalkyl(1-4C)alkylene, which are unsubstituted or substituted with (3-6C)cycloalkyl, (1-6C)alkoxy, CF3 or halogen, and from (6-14C)aryl and (7-15C)aralkyl, wherein the aryl groups are unsubstituted or substituted with (1-6C)alkyl, (3-6C)cycloalkyl, (1-6C)alkoxy, CF3 or halogen;R3 is the same as R2 or is Het-(1-6C)alkyl;R4 is H or (1-3C)alkyl;X and Y are CH or N, with the proviso that they are not both N;Het is a 4-, 5- or 6-membered heterocycle containing one or more heteroatoms selected from O, N and S;m is 1 or 2;p is 1, 2 or 3;q is 1, 2 or 3;t is 2, 3 or 4;or a pharmaceutically acceptable addition salt or solvate thereof.
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(2010/02/11)

Synthesis of an optically pure synthetic intermediate of aloperine from a yeast-reductive product
Optically pure (S)- and (R)-vinylpiperidine 2 and (S)-and (A)-(hydroxyethyl)piperidine 3, which were key intermediates for the synthesis of aloperine, were synthesized from yeast-reductive products.
Yamauchi, Satoshi,Omi, Yasushi
p. 1589 - 1594
(2008/02/02)

Remote Stereocenter Discrimination in the Enzymatic Resolution of Piperidine-2-ethanol. Short Enantioselective Synthesis of Sedamine and Allosedamine
Kinetic resolution of N-Boc-piperidine-2-ethanol (2), a case of remote stereocenter discrimination, was accomplished by sequential transesterification mediated by two enzymes, Lipase PS and porcine pancreatic lipase, showing opposite enantioselectivity. The gram-scale availability of the two enantiomeric N-Boc alcohols 2a (R) and 2c (S) enlarges their synthetic exploitation for the enantioselective preparation of piperidine alkaloids. As an example, the convenient three-step synthesis of both the enantiomers of sedamine and allosedamine is described.
Angoli, Marco,Barilli, Alessio,Lesma, Giordano,Passarella, Daniele,Riva, Sergio,Silvani, Alessandra,Danieli, Bruno
p. 9525 - 9527
(2007/10/03)

Antagonists of gonadotropin releasing hormone
PCT No. PCT/US97/08479 Sec. 371 Date Nov. 12, 1998 Sec. 102(e) Date Nov. 12, 1998 PCT Filed May 16, 1997 PCT Pub. No. WO97/44321 PCT Pub. Date Nov. 27, 1997There are disclosed compounds of formula (I) and pharmaceutical acceptable salts thereof which are useful as antagonists of GnRH and as such may be useful for the treatment of a variety of sex-hormone related conditions.
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(2008/06/13)

Quinolones as gonadotropin releasing hormone (GnRH) antagonists: Simultaneous optimization of the C(3)-aryl and C(6)-substituents
A series of 3-arylquinolones was prepared and evaluated for their ability to act as gonadotropin releasing hormone (GnRH) antagonists. A variety of substitution patterns of the 3-aryl substituent are described. The 3,4,5-trimethylphenyl substituent (23h) was found to be optimal. (C) 2000 Elsevier Science Ltd. All rights reserved.
Young, Jonathan R.,Huang, Song X.,Chen, Irene,Walsh, Thomas F.,DeVita, Robert J.,Wyvratt Jr., Matthew J.,Goulet, Mark T.,Ren, Ning,Lo, Jane,Yang, Yi Tien,Yudkovitz, Joel B.,Cheng, Kang,Smith, Roy G.
p. 1723 - 1727
(2007/10/03)

Investigation of the 4-O-alkylamine substituent of non-peptide quinolone GnRH receptor antagonists
Synthesis and in vitro activity of the enantiomers of quinolone GnRH antagonist (±)-1 are reported. Chiral amino alcohols were prepared from the appropriate cyclic D- or L-amino acids by the Arndt-Eistert homologation followed by reduction of the resulting esters. Incorporation of these pharmacophores was achieved via a novel Mitsunobu alkylation of 4-hydroxyquinolones. The key amine pharmacophore for binding to the rat GnRH receptor was most active in the S-configuration. Ring size was not important for potency with 4, 5, 6, and 7-membered ring amines exhibiting similar potency.
DeVita, Robert J.,Goulet, Mark T.,Wyvratt, Matthew J.,Fisher, Michael H.,Lo, Jane-L,Yang, Yi Tien,Cheng, Kang,Smith, Roy G.
p. 2621 - 2624
(2007/10/03)