1-[2-[4-(3-苯基-2H-苯并吡喃-2-基)苯氧基]乙基]哌啶 | 130064-18-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 1-[2-[4-(3-苯基-2H-苯并吡喃-2-基)苯氧基]乙基]哌啶
• 英文名称: CDRI 85/287
• 英文别名: 2-[4-(2-piperidinoethoxy)phenyl]-3-phenyl-(2H)-1-benzo(b)pyran；2-[4-(2-piperidinoethoxy)phenyl]-3-phenyl-2H-benzo(b)pyran；CDRI-85/287；1-(2-(4-(3-Phenyl-2H-1-benzopyran-2-yl)phenoxy)ethyl)piperidine；1-[2-[4-(3-phenyl-2H-chromen-2-yl)phenoxy]ethyl]piperidine
• CAS: 130064-18-5
• 化学式: C₂₈H₂₉NO₂
• 分子量: 411.544
• InChiKey: DBHGMZQRJDUFGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二对甲苯酰基-L-酒石酸 、 1-[2-[4-(3-苯基-2H-苯并吡喃-2-基)苯氧基]乙基]哌啶 以 乙醇 为溶剂， 反应 4.0h， 以120 mg的产率得到L-2-[4-(2-piperidinoethoxy)phenyl]-3-phenyl-2H-1-benzopyran-di-p-toluoyl-L-tartrate
  参考文献：
  名称：

  Resolution, molecular structure and biological activities of the d - and l -enantiomers of potent anti-implantation agent, dl -2-[4-(2-Piperidinoethoxy)phenyl]-3-phenyl-2 H -1-benzopyran

  摘要：

  Compound 1 (DL-2-[4-(2-piperidinoethoxy)phenyl]-3-phenyl-2H-1-benzopyran, CDRI 85/287) a potent anti-estrogen and anti-implantation agent has been successfully resolved into its pure D- and L-enantiomers. Biological studies showed L-enantiomer to be the active form, exhibiting a fivefold higher receptor affinity for the rat uterine cytosolic estrogen receptor, 100% contraceptive efficacy at 1.3 mg/kg dose in single day schedule and 89% inhibition of estradiol induced increase of uterine weight at its contraceptive dose. The absolute stereochemistry determined by X-ray crystallographic analysis showed that the L-enantiomer has 2R configuration at its asymmetric centre.

  DOI：

  10.1016/s0968-0896(99)00131-5
• 作为产物：
  描述：

  2-(4-hydroxyphenyl)-3-phenyl-2H-1-benzopyran 生成 1-[2-[4-(3-苯基-2H-苯并吡喃-2-基)苯氧基]乙基]哌啶
  参考文献：
  名称：

  SHARMA, ARUN P.;SAEED, ASHRAF;DURANI, SUSHEEL;KAPIL, RANDHIR S., J. MED. CHEM., 33,(1990) N2, C. 3216-3222

  摘要：

  DOI：

文献信息

• Structure-activity relationship of antiestrogens. Effect of the side chain and its position on activity of 2,3-diaryl-2H-1-benzopyrans
  作者：Arun P. Sharma、Ashraf Saeed、Susheel Durani、Randhir S. Kapil

  DOI：10.1021/jm00174a019

  日期：1990.12

  A series of 2,3-diaryl-2H-1-benzopyrans carrying a tertiary aminoethoxy chain at the ortho, meta, or para position of 2-phenyl or an alkyl at position 4 of the pyran ring were synthesized and evaluated for their affinity for estrogen receptor (ER) and for microsomal antiestrogen specific binding site and for their uterotrophic-antiuterotrophic activities in rodents. The analogues bearing the side chain at the para position of 2-phenyl were found to be active while those substituted at the meta and ortho positions were inactive as ER ligands as well as estrogen agonists-antagonists. Among para-substituted ethers, the 2-piperidinoethoxy analogue 5 was found to be a more effective antiestrogen than the corresponding pyrrolidino, dimethylamino, and related analogues. Incorporation of a methyl or an ethyl at C4 in the pyran nucleus was found to increase receptor affinity of the prototypes. The ethyl was also found to potentiate agonist activity of the prototype while abolishing its antagonist activity. The piperidino analogue 5 was found to be a better antiestrogen than tamoxifen as well as LY-117018 in rats as well as mice. The prototypes were also found to have high affinity for the microsomal antiestrogen specific binding sites. The benzopyrans have thus emerged as a new group of potent antiestrogens.
• 2,3-DIARYL-1-BENZOPYRANS FOR TREATING DERMATITIS
  申请人：ZymoGenetics, Inc.

  公开号：EP0737068A1

  公开（公告）日：1996-10-16
• US5389646A
  申请人：——

  公开号：US5389646A

  公开（公告）日：1995-02-14
• US5416098A
  申请人：——

  公开号：US5416098A

  公开（公告）日：1995-05-16
• US5552413A
  申请人：——

  公开号：US5552413A

  公开（公告）日：1996-09-03