3-((-bis(2-methylphenyl)-1-propen-3-yl)oxy)-1-propanol | 136059-54-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-((-bis(2-methylphenyl)-1-propen-3-yl)oxy)-1-propanol
• 英文别名: 3-(3,3-bis(2-methyl phenyl)-2-propen-1-yloxy)-1-propanol；3-(3,3-bis(2-methylphenyl)-2-propen-1-yloxy)-1-propanol；3-[3,3-bis(2-methylphenyl)prop-2-enoxy]propan-1-ol
• CAS: 136059-54-6
• 化学式: C₂₀H₂₄O₂
• 分子量: 296.409
• InChiKey: HIBOPZGRSWIEAR-UHFFFAOYSA-N

物化性质

• 沸点：
  470.7±34.0 °C(Predicted)
• 密度：
  1.048±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-((-bis(2-methylphenyl)-1-propen-3-yl)oxy)-1-propanol 在 sodium hydroxide 、 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， 反应 14.0h， 生成 (R)-N-(3-(3,3-Bis(2-Methylphenyl)-2-propen-1-yloxy)-1-propyl)-3-piperidinecarboxylic acid
  参考文献：
  名称：

  Synthesis of Novel GABA Uptake Inhibitors. 4. Bioisosteric Transformation and Successive Optimization of Known GABA Uptake Inhibitors Leading to a Series of Potent Anticonvulsant Drug Candidates

  摘要：

  By bioisosteric transformations and successive optimization of known GABA uptake inhibitors, several series of novel GABA uptake inhibitors have been prepared by different synthetic approaches. These compounds are derivatives of nipecotic acid and guvacine, substituted at the nitrogen of these amino acids by various lipophilic moieties such as diarylaminoalkoxyalkyl or diarylalkoxyalkyl. The in vitro values for inhibition of [H-3]GABA uptake in rat synaptosomes was determined for each compound, and it was found that the most potent compound from this series, (R)-1-(2-(3,3-diphenyl-1-propyloxy)ethyl)-3-piperidinecarboxylic acid hydrochloride (29), is so far the most potent parent compound inhibiting GABA uptake into synaptosomes. Structure-activity results confirm our earlier observations, that an electronegative center in the chain connecting the amino acid and diaryl moiety is very critical in order to obtain high in vitro potency. Several of the novel compounds were also evaluated for their ability in vivo to inhibit clonic seizures induced by a 15 mg/kg (ip) dose of methyl 6,7-dimethoxy-4-ethyl-beta-carboline-3-carboxylate (DMCM). Some of the compounds tested show a high in vivo potency comparable with that of the recently launched anticonvulsant product 6 ((R)-1-(4,4-bis(3-methyl-2-thienyl)-3-butenyl)-3-piperidinecarboxylic acid).

  DOI：

  10.1021/jm980492e
• 作为产物：
  描述：

  3-Bromo-1,1-bis(2-methyl-phenyl)-1-propene 、 1,3-丙二醇 在 正丁基锂 作用下， 以 正庚烷 、 水 、 乙酸乙酯 为溶剂， 以31%的产率得到3-((-bis(2-methylphenyl)-1-propen-3-yl)oxy)-1-propanol
  参考文献：
  名称：

  Method of treating filariae

  摘要：

  这项发明涉及一种治疗患有丝虫病的哺乳动物的新方法。

  公开号：

  US06174898B1

文献信息

• Heterocyclic carboxylic acids
  申请人：Novo Nordisk A/S

  公开号：US05198451A1

  公开（公告）日：1993-03-30

  Novel N-substituted azaheterocyclic carboxylic acids and esters thereof in which a substituted alkyl chain forms part of the N-substituent, the compounds thus having the general formula I ##STR1## wherein Y is ##STR2## wherein R.sup.1 and R.sup.2 independently are C.sub.3-8 cycloalkyl phenyl or thienyl all of which may be optionally substituted with halogen, trifluoromethyl, C.sub.1-16 alkyl or C.sub.1-6 alkoxy; s is 1, 2 or 3; x is --CH.sub.2 --, --O-- or ##STR3## -wherein R.sup.3 is hydrogen or C.sub.1-6 -alkyl; r is 2, 3 or 4; R.sup.4 and R.sup.5 each represents hydrogen or may together represent a bond and R.sup.6 is OH or C.sub.1-8 -alkoxy; and pharmaceutically acceptable acid addition salts are potent inhibitors of GABA uptake from the synaptic cleft.

  N-取代的杂环羧酸和其酯，其中取代的烷基链构成N-取代基的一部分，因此这些化合物具有一般式I ##STR1## 其中Y为##STR2## 其中R.sup.1和R.sup.2独立地为C.sub.3-8环烷基苯或噻吩基，所有这些基可能选择性地被卤素、三氟甲基、C.sub.1-16烷基或C.sub.1-6烷氧基取代；s为1、2或3；x为--CH.sub.2--、--O--或##STR3## -其中R.sup.3为氢或C.sub.1-6-烷基；r为2、3或4；R.sup.4和R.sup.5各代表氢或可共同代表键，R.sup.6为OH或C.sub.1-8-烷氧基；和药学上可接受的酸盐是GABA从突触间隙中摄取的有效抑制剂。
• N-SUBSTITUTED AZAHETEROCYCLIC CARBOXYLIC ACIDS AND A PHARMACEUTICAL COMPOSITION
  申请人：NOVO NORDISK A/S

  公开号：EP0502031A1

  公开（公告）日：1992-09-09
• A METHOD OF TREATING FILARIAE
  申请人：NOVO NORDISK A/S

  公开号：EP0858339A1

  公开（公告）日：1998-08-19
• US5198451A
  申请人：——

  公开号：US5198451A

  公开（公告）日：1993-03-30
• US6174898B1
  申请人：——

  公开号：US6174898B1

  公开（公告）日：2001-01-16