(-)-SYA 09 | 154956-81-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-SYA 09
• 英文别名: (-)-4-[3-(4-chlorophenyl)-3-hydroxypyrrolidin-1-yl]-1-(4-fluorophenyl)butan-1-one；4-(3-(4-Chlorophenyl)-3-hydroxypyrrolidin-1-yl)-1-(4-fluorophenyl)butan-1-one；4-[3-(4-chlorophenyl)-3-hydroxypyrrolidin-1-yl]-1-(4-fluorophenyl)butan-1-one
• CAS: 154956-81-7
• 化学式: C₂₀H₂₁ClFNO₂
• 分子量: 361.844
• InChiKey: BETHXCLHMRGYBW-UHFFFAOYSA-N

物化性质

• 沸点：
  517.4±50.0 °C(Predicted)
• 密度：
  1.267±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-(4-chloro-phenyl)-3-hydroxy-pyrrolidine-1-carboxylic acid ethyl ester 在 氢氧化钾 、 potassium carbonate 、 potassium iodide 作用下， 以 乙二醇二甲醚 、 乙醇 为溶剂， 反应 12.0h， 生成 (-)-SYA 09
  参考文献：
  名称：

  Evaluation of the eutomer of 4-{3-(4-chlorophenyl)-3-hydroxypyrrolidin-1-yl}-1-(4-fluorophenyl)butan-1-one, {(+)-SYA 09}, a pyrrolidine analog of haloperidol

  摘要：

  Enantionteric separation of the racemic 4-{3-(4-chlorophenyl)-3-hydroxypyrrolidin-1-yl}-1-(4-fluorophenyl)butan-1-one, a pyrrolidine analog of haloperidol, {(+/-)-SYA 09}, and subsequent binding studies revealed that most of the binding affinity at dopamine and serotonin receptors resides in the (+)-isomer {(+)-SYA 09} or the eutomer. Further pharmacological evaluation of the eutomer revealed that it has a higher affinity for the dopamine D4 (DAD4) receptor subtype (K-i = 3.6 nM) than for the DAD2 subtype (K-i = 51.1 nM) with a ratio of 14.2 (D2K(i)/D4K(i) ratio = 14.2). In an animal model of antipsychotic efficacy, the (+)-SYA 09 was efficacious with an ED50 value of 1.6 mg/kg, ip, and at twice this value, (+)-SYA 09 did not induce significant catalepsy in rats. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.03.057

文献信息

• DISUBSTITUTED PHENYLPYRROLIDINES AS MODULATORS OF CORTICAL CATECHOLAMINERGIC NEUROTRANSMISSION
  申请人：Sonesson Clas

  公开号：US20100179211A1

  公开（公告）日：2010-07-15

  The present invention relates to the use of compounds which increase extracellular levels of catecholamines, dopamine and norepinephrine, in cerebral cortical areas of the mammalian brain, and more specifically to the use of 3-disubstituted phenyl-1-pyrrolidinols for the treatment of central nervous system disorders.

  本发明涉及利用增加哺乳动物大脑脑皮层区域儿茶酚胺、多巴胺和去甲肾上腺素的细胞外水平的化合物，更具体地涉及利用3-二取代苯基-1-吡咯烷醇治疗中枢神经系统疾病。
• Haloperidol analogs
  申请人：Ablordeppey Y. Seth

  公开号：US20060052363A1

  公开（公告）日：2006-03-09

  Haloperidol analogs that conforms to the structural formulae: wherein: R is H, or —(CH 2 ) n —OH, n is an integer from 0 to 2, and A is a heterocyclic bridging group, consisting essentially of carbon and at least one nitrogen atom, which effectively maintains the distance between the moieties connected thereby such that the compound (1) is incapable of metabolizing to BCPP + like species, (2) has an affinity for the D2 receptor subtype of 15

  氟哌啶酮类似物符合以下结构式：其中：R为H，或—(CH2)n—OH，n为0至2的整数，且A为杂环桥接基团，主要由碳和至少一个氮原子组成，有效地保持连接的基团之间的距离，使得化合物（1）无法代谢为BCPP+类似物，具有对D2受体亚型的亲和力15
• US7700587B2
  申请人：——

  公开号：US7700587B2

  公开（公告）日：2010-04-20
• US8188301B2
  申请人：——

  公开号：US8188301B2

  公开（公告）日：2012-05-29
• [EN] HALOPERIDOL ANALOGS<br/>[FR] ANALOGUES DE L'HALOPÉRIDOL
  申请人：FLORIDA A & M UNIVERSITY

  公开号：WO2007053145A1

  公开（公告）日：2007-05-10

  [EN] Haloperidol analogs that conforms to the structural formulae [I]; wherein: R is H, or -(CH₂)_n-OH, n is an integer from 0 to 2, and A is a heterocyclic bridging group, consisting essentially of carbon and at least one nitrogen atom, which effectively maintains the distance between the moieties connected thereby such that the compound (1) is incapable of metabolizing to BCPP⁺ like species, (2) has an affinity for the D2 receptor subtype of 15 < D2 < 250 and (3) functions as a dopamine receptor antagonist, or the structural formulae [II]; wherein: R₁ is H, or -(CH₂)_n-OH, n is an integer from 0 to 2, B is an aza- or diaza-bicylo group, which effectively maintains the distance between the moieties connected thereby such that the compound is incapable of metabolizing to BCPP⁺ like species; and Z is -CH- or N; and pharmaceutically acceptable salts, esters, derivatives, metal complexes, conjugates and prodrugs thereof.
  [FR] L'invention concerne des analogues de l'halopéridol qui correspondent aux formules de structure [I] (dans lesquelles : R est H ou -(CH₂)_n-OH, n est un nombre entier allant de 0 à 2 et A est un groupe de pontage hétérocyclique, constitué essentiellement de carbone et d'au moins un atome d'azote, lequel maintient de façon efficace la distance entre les entités reliées par celui-ci à une valeur telle que le composé (1) ne puisse pas être métabolisé en espèces ressemblant à BCPP⁺, (2) ait une affinité pour le sous-type des récepteurs D2 tel que 15 < D2 < 250 et (3) agisse comme un antagoniste des récepteurs dopaminergiques) ou aux formules de structure [II] (dans lesquelles : R₁ est H ou -(CH₂)_n-OH, n est un nombre entier allant de 0 à 2, B est un groupe azabicyclo ou diazabicyclo, lequel maintient de façon efficace la distance entre les entités reliées par celui-ci à une valeur telle que le composé ne puisse pas être métabolisé en espèces ressemblant à BCPP⁺ ; et Z est -CH- ou N) ; et sels, esters, dérivés, complexes de métaux, conjugués et promédicaments acceptables du point de vue pharmaceutique de ceux-ci.