4-(p-Chloro-α-hydroxybenzyl)-1-[3-(p-fluorobenzoyl)propyl]piperidine | 38077-13-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(p-Chloro-α-hydroxybenzyl)-1-[3-(p-fluorobenzoyl)propyl]piperidine
• 英文别名: gamma-[4-(p-Chloro-alpha-hydroxybenzyl)piperidino]-p-fluorobutyrophenone；4-[4-[(4-chlorophenyl)-hydroxymethyl]piperidin-1-yl]-1-(4-fluorophenyl)butan-1-one
• CAS: 38077-13-3
• 化学式: C₂₂H₂₅ClFNO₂
• 分子量: 389.897
• InChiKey: DLIITBUFJWYNOW-UHFFFAOYSA-N

物化性质

• 沸点：
  534.4±40.0 °C(Predicted)
• 密度：
  1.217±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 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：

  2-(3-氯丙基)-2-(4-氟苯基)-1,3-二氧戊烷 在 盐酸 、 sodium borohydrid 作用下， 以 乙醇 、 氯仿 、 正丁醇 为溶剂， 生成 4-(p-Chloro-α-hydroxybenzyl)-1-[3-(p-fluorobenzoyl)propyl]piperidine
  参考文献：
  名称：

  Method for inhibiting emesis and compositions therefor

  摘要：

  本发明揭示了具有有用的抗恶心性能的1,4-(3-)二取代哌啶类化合物。这些化合物具有一般式：其中R是卤素，R.sup.1是氢和卤素，n是从2到4的正整数，A是--C(O)--和--CHOH--。这些基本化合物的药用可接受的酸盐特别用作抗恶心剂。

  公开号：

  US04101662A1

文献信息

• Design, Synthesis, and Evaluation of Metabolism-Based Analogues of Haloperidol Incapable of Forming MPP+-like Species
  作者：M. Lyles-Eggleston、R. Altundas、J. Xia、D. M. N. Sikazwe、P. Fan、Q. Yang、S. Li、W. Zhang、X. Zhu、A. W. Schmidt、M. Vanase-Frawley、A. Shrihkande、A. Villalobos、R. F. Borne、S. Y. Ablordeppey

  DOI：10.1021/jm0301033

  日期：2004.1.1

  The long-term, irreversible, Parkinsonism-like side effects of haloperidol have been speculated to involve several mechanisms. More recently, it has been speculated that the metabolic transformation to MPP+-like species may contribute to the Parkinsonism-like side effects. Because BCPP+ and its reduced analogue have been shown to possess the potential to destroy dopamine receptors in the nigrostriatum, we have designed new analogues of haloperidol lacking the structural features necessary to form neurotoxic quaternary species but retaining their dopamine-binding capacity. The most potent agent at the D2 receptor, the homopiperidine analogue 11, was found to be equipotent to haloperidol. It was also of interest to identify analogues with DA binding profiles similar to that of clozapine at the dopamine receptor subtypes. Evaluation of the proposed agents shows that the ratio of D2 to D4 (2) binding of clozapine was mimicked by 7 [K-i(D2) = 33, K-i(D3) = 200, K-i(D4) = 11 nM; K-i(D2)/K-i(D4) = 3] and 9 [K-i(D2) = 44, K-i(D3) = 170, K-i(D4) = 24 nM; K-i(D2)/K-i(D4) = 2]. A preliminary in-vivo testing of compound 7 shows that its behavioral profile is similar to that of clozapine. This profile suggests that there is a need for further evaluation of these two synthetic agents and their enantiomers for efficacy and lack of catalepsy in animal models.
• US4101662A
  申请人：——

  公开号：US4101662A

  公开（公告）日：1978-07-18
• Method for inhibiting emesis and compositions therefor
  申请人：A. H. Robins Company, Incorporated

  公开号：US04101662A1

  公开（公告）日：1978-07-18

  1,4-(3-)Disubstituted piperidines are disclosed which have useful antiemetic properties. The compounds have the general formula: ##STR1## wherein R is halogen, R.sup.1 is hydrogen and halogen, n is a positive integer from 2-4 and A is --C(O)-- and --CHOH--. The pharmaceutically acceptable acid addition salts of the basic compounds are particularly useful as antiemetics.

  本发明揭示了具有有用的抗恶心性能的1,4-(3-)二取代哌啶类化合物。这些化合物具有一般式：其中R是卤素，R.sup.1是氢和卤素，n是从2到4的正整数，A是--C(O)--和--CHOH--。这些基本化合物的药用可接受的酸盐特别用作抗恶心剂。