3-(4-氟苯基)-6-甲基茚满-1-酮 | 80272-23-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 中文名称: 3-(4-氟苯基)-6-甲基茚满-1-酮
• 中文别名: 乙基2-羰基环壬烷羧酸酯
• 英文名称: 3-(4'-fluoro-phenyl)-6-methyl-1-indanone
• 英文别名: 3-(4'-fluorophenyl)-6-methyl-1-indanone；3-(4-Fluorophenyl)-6-methylindan-1-one；3-(4-fluorophenyl)-6-methyl-2,3-dihydroinden-1-one
• CAS: 80272-23-7
• 化学式: C₁₆H₁₃FO
• 分子量: 240.277
• InChiKey: DMZGDJOWXYJRMX-UHFFFAOYSA-N

物化性质

• 沸点：
  357.7±42.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-氟苯基)-6-甲基茚满-1-酮 在 sodium tetrahydroborate 、 氯化亚砜 作用下， 以 甲醇 、 甲苯 、 丁酮 为溶剂， 反应 18.5h， 生成 Lu 17-050
  参考文献：
  名称：

  Neuroleptic activity and dopamine-uptake inhibition in 1-piperazino-3-phenylindans

  摘要：

  A series of 1-piperazino-3-phenylindans was synthesized and tested for neuroleptic and thymoleptic activity. Neuroleptic activity was found only in trans racemates and was associated with one of the enantiomers only. The potent and long-acting neuroleptic compound trans-4-[3-(4-fluorophenyl)-6-(trifluoromethyl)indan-1-yl]-1-piperazineethanol (Lu 18-012, tefludazine) was developed by systematic variation of structural components. Thymoleptic activity was optimized, especially with respect to dopamine-uptake inhibition. No geometrical stereoselectivity was found with regard to dopamine-uptake inhibition, but a high enantioselectivity could be demonstrated for both cis and trans racemates. The most potent compounds were 1-piperazino-3-(3,4-dichlorophenyl)indans with IC50 values of about 2nM for inhibition of dopamine uptake.

  DOI：

  10.1021/jm00361a002
• 作为产物：
  描述：

  3-(4-氟苯基)-3-(4-甲基苯基)丙酸 在 PPA 作用下， 以 正己烷 、 异丙醚 为溶剂， 生成 3-(4-氟苯基)-6-甲基茚满-1-酮
  参考文献：
  名称：

  Indane derivatives, pharmaceutical compositions thereof and method of

  摘要：

  本发明涉及新的1-哌嗪基-3-苯基-茚衍生物，具有明显的精神药理学活性，如神经阻滞活性、镇痛活性、抗抑郁活性，并且同时具有低程度的不良副作用，制备该茚衍生物的方法、含有该茚衍生物的制药组合物，以及通过向生物体，包括人类，施用所述衍生物之一的治疗有效量来治疗精神障碍，如精神病和抑郁症以及疼痛的方法。

  公开号：

  US04443448A1

文献信息

• Anti-psychotic phenylindene derivatives and acid addition salts thereof
  申请人：Kefalas A/S

  公开号：US04525360A1

  公开（公告）日：1985-06-25

  The present invention relates to novel phenylindene derivatives having interesting pharmacodynamic properties which make them useful as psychopharmacologicals in the treatment especially of psychoses such as schizophrenia, having a low degree of undesired side effects such as cataleptic effects, methods for the preparation of said phenylindene derivatives, pharmaceutical compositions containing same, and methods for the treatment of psychic disorders, such as psychoses and depressions and pain, by administering a therapeutically active amount of one of said derivatives to a living animal body, including human beings.

  本发明涉及具有有趣的药效学特性的新型苯基茚衍生物，这使它们在治疗精神分裂症等精神病时非常有用，具有低不良副作用（如痉挛效应）的程度，以及制备该苯基茚衍生物的方法，含有相同成分的药物组合物，以及通过向生物体（包括人类）施用所述衍生物之一的治疗活性量来治疗心理障碍，如精神病、抑郁症和疼痛的方法。
• Indane derivatives, pharmaceutical compositions thereof and method of
  申请人：Kefalas A/S

  公开号：US04443448A1

  公开（公告）日：1984-04-17

  The present invention relates to novel 1-piperazino-3-phenyl-indane derivatives which have pronounced psychopharmacological activity such as neuroleptic activity, analgesic activity, antidepressant activity and, at the same time, a low degree of undesired side-effects, methods for the preparation of said indane derivatives, pharmaceutical compositions containing same, and methods for the treatment of psychic disorders, such as psychoses and depressions and pain, by administering a therapeutically active amount of one of said derivatives to a living animal body, including human beings.

  本发明涉及新的1-哌嗪基-3-苯基-茚衍生物，具有明显的精神药理学活性，如神经阻滞活性、镇痛活性、抗抑郁活性，并且同时具有低程度的不良副作用，制备该茚衍生物的方法、含有该茚衍生物的制药组合物，以及通过向生物体，包括人类，施用所述衍生物之一的治疗有效量来治疗精神障碍，如精神病和抑郁症以及疼痛的方法。
• Indane derivatives, methods of their preparation and compositions containing them
  申请人：KEFALAS A/S

  公开号：EP0035363A1

  公开（公告）日：1981-09-09

  1-Piperazino-3-phenylindane derivatives of the formula: wherein R1, R2, R3 and R4 are as defined in Claim 1, and their pharmaceutically acceptable acid addition salts. The compounds are prepared by the usual methods for analogous compounds. They have been found to have psychopharmacological and analgetic activity. Pharmaceutical compositions containing the compounds have been disclosed.

  式中 R1、R2、R3 和 R4 如权利要求 1 所定义的 1-哌嗪基-3-苯基茚满衍生物及其药学上可接受的酸加成盐。 这些化合物是用类似化合物的常规方法制备的。 它们具有精神药理学和镇痛活性。 含有这些化合物的药物组合物已被公开。
• Phenylindene derivatives, acid addition salts thereof, and methods of preparation
  申请人：KEFALAS A/S

  公开号：EP0110521A2

  公开（公告）日：1984-06-13

  Novel phenylindene derivatives of the present invention are represented by the following formula: wherein the dotted lines indicate optional bonds; R1 is hydrogen, halogen, lower alkyl, lower alkoxy, hydroxymethyl, lower alkoxymethyl, cyano, trifluoromethyl, lower alkylthio or lower alkylsulfonyl; R2 is halogen, lower alkyl or trlfluoromethyl; and R3 is hydrogen, alkyl or alkenyl (straight or branched chain with C1-C6 inclusive) optionally substituted with one or two hydroxy groups, any hydroxy group present being optionally esterified with an aliphatic carboxylic acid having from two to twenty-four carbon atoms inclusive, or R3 is wherein Z ist NR4, 0 or S, where R4 is H or lower alkyl, and W is 0 or S, as well as pharmaceutically acceptable acid addition salts of the compounds of Formula I. The phenylindene derivatives of Formula I have Interesting pharmacodynamic properties indicating strong antipsychotic activity. Methods for the preparation of said derivatives are also described, as well as novel intermediates, wich are useful in the methods.

  本发明的新型苯基茚衍生物由下式表示： 其中虚线表示任选键； R1 是氢、卤素、低级烷基、低级烷氧基、羟甲基、低级烷氧基甲基、氰基、三氟甲基、低级烷硫基或低级烷基磺酰基； R2 是卤素、低级烷基或三氟甲基；以及 R3 是氢、烷基或烯基（直链或支链，C1-C6 包括在内），可选择被一个或两个羟基取代，存在的任何羟基可选择与具有 2 至 24 个碳原子（包括在内）的脂肪族羧酸酯化，或 R3 是 其中 Z 是 NR4、0 或 S，其中 R4 是 H 或低级烷基，W 是 0 或 S，以及式 I 化合物的药学上可接受的酸加成盐。 式 I 的苯基茚衍生物具有有趣的药效学特性，表明其具有很强的抗精神病活性。 此外，还介绍了制备上述衍生物的方法，以及在这些方法中有用的新型中间体。
• BOGESO, K. P., J. MED. CHEM., 1983, 26, N 7, 935-947
  作者：BOGESO, K. P.

  DOI：——

  日期：——