7-(3-Chloropropoxy)-3-formyl-chromen-4-one | 172739-48-9

• 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)-3-formyl-chromen-4-one
• 英文别名: 7-(3-Chloropropoxy)-4-oxochromene-3-carbaldehyde
• CAS: 172739-48-9
• 化学式: C₁₃H₁₁ClO₄
• 分子量: 266.681
• InChiKey: BWBGFVCFGLWGJL-UHFFFAOYSA-N

物化性质

• 沸点：
  443.2±45.0 °C(Predicted)
• 密度：
  1.403±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-(3-Chloropropoxy)-3-formyl-chromen-4-one 在 甲醇 、 sodium tetrahydroborate 、 potassium carbonate 、 potassium iodide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 18.0h， 生成 阿巴哌酮
  参考文献：
  名称：

  7-[3-(1-Piperidinyl)propoxy]chromenones as Potential Atypical Antipsychotics. 2. Pharmacological Profile of 7-[3-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)-piperidin-1-yl]propoxy]-3-(hydroxymethyl)chromen-4-one (Abaperidone, FI-8602)

  摘要：

  A series of novel 7-[3-(1-piperidinyl)propoxy]chromenones was synthesized and tested as potential antipsychotics in several in vitro and in vivo assays. The compounds possessed good affinity for Dp receptors, together with a greater affinity for 5-HT2 receptors, a profile which has been proposed as a model for atypical antipsychotics. Several agents also displayed a high potency in the climbing mice assay on oral administration, suggesting a potent antipsychotic effect as compared to reference standards. Compound 23 was selected for fur ther pharmacological evaluation. induction of catalepsy and inhibition of stereotypies weaker than standards, along with a lower increase in serum prolactin levels, were indicative of a potential atypical profile for this compound. From these results, 7-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidin-1-yl]propoxy]-3-(hydroxymethyl)chromen-4-one (23, abaperidone) has been proposed for clinical evaluation in humans as a potential atypical antipsychotic.

  DOI：

  10.1021/jm9810396
• 作为产物：
  描述：

  1-[4-(3-氯丙氧基)-2-羟基苯基]乙酮 在 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以12 g (51%)的产率得到7-(3-Chloropropoxy)-3-formyl-chromen-4-one
  参考文献：
  名称：

  4-p-fluorobenzoyl-1-piperidinyl-propoxy-chromen-4-one derivatives, their

  摘要：

  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。

  公开号：

  US05643927A1

文献信息

• 7-[3-(1-Piperidinyl)propoxy]chromenones as Potential Atypical Antipsychotics
  作者：Jordi Bolós、Santiago Gubert、Lluís Anglada、Josep M. Planas、Carme Burgarolas、Josep M. Castelló、Aurelio Sacristán、José A. Ortiz

  DOI：10.1021/jm950894b

  日期：1996.1.1

  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.
• J. Med. Chem. 1996, 39, 2962-2970
  作者：

  DOI：——

  日期：——
• J. Med. Chem. 1998, 41, 5402-5409
  作者：

  DOI：——

  日期：——
• 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