7-(3-Chloropropoxy)-2-trifluoromethylchromen-4-one | 172739-44-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 7-(3-Chloropropoxy)-2-trifluoromethylchromen-4-one
• 英文别名: 7-(3-Chloropropoxy)-2-(trifluoromethyl)chromen-4-one
• CAS: 172739-44-5
• 化学式: C₁₃H₁₀ClF₃O₃
• 分子量: 306.669
• InChiKey: VJXKIMPVQIBWNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(4-氟苯甲酰基)哌啶 、 7-(3-Chloropropoxy)-2-trifluoromethylchromen-4-one 在 potassium carbonate 、 potassium iodide 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 7-[3-[4-(4-Fluorobenzoyl)piperidin-1-yl]propoxy]-2-(trifluoromethyl)chromen-4-one
  参考文献：
  名称：

  7-[3-(1-Piperidinyl)propoxy]chromenones as Potential Atypical Antipsychotics

  摘要：

  Compound 1 (1-benzyl-3-methyl-4-[4-(4-fluorophenyl)- a synthetic intermediate identified as a potential atypical antipsychotic, was selected as the starting point for pharmacological improvement. From 1, sequential structural variations were conducted in order to improve its potency and oral bioavailability. These variations included a series of piperazine, ethanediamine, and piperidine derivatives. The piperidine series afforded some orally potent compounds in the inhibition of apomorphine-induced climbing and hyperactivity in mice, which are regarded as behavioral models predictive of antipsychotic efficacy. Further optimization of these structures led to the highly potent 7-[3-(1-piperidinyl)propoxy]chromenones. Inhibition of stereotypies and induction of catalepsy in rats at doses substantially higher than required for inhibition of climbing suggest an atypical antipsychotic profile, which is assumed to predict a reduced induction of extrapyramidal side effects in humans.

  DOI：

  10.1021/jm950894b
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 在 potassium carbonate 、 三氟乙酸酐 作用下， 以 丙酮 为溶剂， 反应 64.0h， 生成 7-(3-Chloropropoxy)-2-trifluoromethylchromen-4-one
  参考文献：
  名称：

  7-[3-(1-Piperidinyl)propoxy]chromenones as Potential Atypical Antipsychotics

  摘要：

  Compound 1 (1-benzyl-3-methyl-4-[4-(4-fluorophenyl)- a synthetic intermediate identified as a potential atypical antipsychotic, was selected as the starting point for pharmacological improvement. From 1, sequential structural variations were conducted in order to improve its potency and oral bioavailability. These variations included a series of piperazine, ethanediamine, and piperidine derivatives. The piperidine series afforded some orally potent compounds in the inhibition of apomorphine-induced climbing and hyperactivity in mice, which are regarded as behavioral models predictive of antipsychotic efficacy. Further optimization of these structures led to the highly potent 7-[3-(1-piperidinyl)propoxy]chromenones. Inhibition of stereotypies and induction of catalepsy in rats at doses substantially higher than required for inhibition of climbing suggest an atypical antipsychotic profile, which is assumed to predict a reduced induction of extrapyramidal side effects in humans.

  DOI：

  10.1021/jm950894b

文献信息

• 4-p-fluorobenzoyl-1-piperidinyl-propoxy-chromen-4-one derivatives, their
  申请人：Ferrer Internacional, S.A.

  公开号：US05643927A1

  公开（公告）日：1997-07-01

  The present invention relates to new chromene compounds of the general formula (I): ##STR1## wherein R.sub.1 and R.sub.2 are hydrogen, alkyl having from 1 to 4 carbon atoms, halogen, trifluoromethyl, optionally substituted phenyl, or hydroxymethyl, as well as their pharmaceutically acceptable addition salts. These compounds are useful in the treatment of psychosis and schizophrenia.

  本发明涉及一般式（I）的新的咔咯酮化合物：其中R₁和R₂为氢、具有1至4个碳原子的烷基、卤素、三氟甲基、可选取代的苯基或羟甲基，以及它们的药用可接受的加合物盐。这些化合物在治疗精神病和精神分裂症中有用。
• 4-P-FLUOROBENZOYL-1-PIPERIDINYL-PROPOXY-CHROMEN-4-ONE DERIVATIVES, THEIR PREPARATION AND THEIR USE IN THE TREATMENT OF PSYCHOSIS AND SCHIZOPHRENIA
  申请人：FERRER INTERNACIONAL, S.A.

  公开号：EP0699197A1

  公开（公告）日：1996-03-06
• US5643927A
  申请人：——

  公开号：US5643927A

  公开（公告）日：1997-07-01
• [EN] 4-P-FLUOROBENZOYL-1-PIPERIDINYL-PROPOXY-CHROMEN-4-ONE DERIVATIVES, THEIR PREPARATION AND THEIR USE IN THE TREATMENT OF PSYCHOSIS AND SCHIZOPHRENIA<br/>[FR] DERIVES 4-P-FLUOROBENZOYL-1-PIPERIDINYL-PROPOXY-CHROMEN-4-ONE, LEUR PREPARATION ET LEUR UTILISATION DANS LE TRAITEMENT DES PSYCHOSES ET DE LA SCHIZOPHRENIE
  申请人：FERRER INTERNACIONAL, S.A.

  公开号：WO1995025733A1

  公开（公告）日：1995-09-28

  (EN) The present invention relates to new chromene compounds of general formula (I), wherein R1 and R2 are hydrogen, alkyl having from 1 to 4 carbon atoms, halogen, trifluoromethyl, optionally substituted phenyl, or hydroxymethyl, as well as their pharmaceutically acceptable addition salts. These compounds are useful in the treatment of psychosis and schizophrenia.(FR) Nouveaux composés chromène de la formule générale (I), ainsi que leurs sels d'addition pharmacologiquement acceptables, dans laquelle R1 et R2 représentent hydrogène, alcoyle possédant de 1 à 4 atomes de carbone, halogène, trifluorométhyle, phényle facultativement substitué, ou hydroxyméthyle. Ces composés sont utiles dans le traitement des psychoses et de la schizophrénie.