(3S,4S)-7-methoxy-3-(4-methoxyphenyl)-3-methyl-4-(2-propenyl)thiochroman | 344456-58-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫铬烷
• 英文名称: (3S,4S)-7-methoxy-3-(4-methoxyphenyl)-3-methyl-4-(2-propenyl)thiochroman
• 英文别名: (3S,4S)-7-methoxy-3-(4-methoxyphenyl)-3-methyl-4-prop-2-enyl-2,4-dihydrothiochromene
• CAS: 344456-58-2
• 化学式: C₂₁H₂₄O₂S
• 分子量: 340.486
• InChiKey: COBGZZKFELEIQP-TZIWHRDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,4S)-7-methoxy-3-(4-methoxyphenyl)-3-methyl-4-(2-propenyl)thiochroman 在 palladium on activated charcoal sodium hydroxide 、 Grubbs catalyst first generation 、 氢气 、 三溴化硼 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 10-[(3S,4S)-7-Hydroxy-3-(4-hydroxy-phenyl)-3-methyl-thiochroman-4-yl]-2-(5,5,6,6,6-pentafluoro-hexyl)-decanoic acid
  参考文献：
  名称：

  Discovery of thiochroman derivatives bearing a carboxy-containing side chain as orally active pure antiestrogens

  摘要：

  In order to search for alternatives to the sulfoxide moiety in the long side chain of pure antiestrogens, several molecules that may interact with water in a fashion similar to ICI164,384 were designed and it was found that compounds with the carboxy, the sulfamide, or the sulfonamide instead of the sulfoxide moiety also functioned as pure antiestrogens. Interestingly, the compound possessing the carboxy moiety showed superior antiestrogen activity compared to ICI182,780 when dosed orally. Results of the pharmacokinctic evaluation indicated that the potent antiestrogen activity at oral dosing attributed to both the improved absorption from the intestinal wall and the metabolic stability of the compound in liver. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.090
• 作为产物：
  描述：

  7-Methoxy-3-(4-methoxyphenyl)-3-methylthiochroman-4-one 在 lithium aluminium tetrahydride 、 zinc(II) iodide 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 生成 (3S,4S)-7-methoxy-3-(4-methoxyphenyl)-3-methyl-4-(2-propenyl)thiochroman
  参考文献：
  名称：

  Discovery of thiochroman derivatives bearing a carboxy-containing side chain as orally active pure antiestrogens

  摘要：

  In order to search for alternatives to the sulfoxide moiety in the long side chain of pure antiestrogens, several molecules that may interact with water in a fashion similar to ICI164,384 were designed and it was found that compounds with the carboxy, the sulfamide, or the sulfonamide instead of the sulfoxide moiety also functioned as pure antiestrogens. Interestingly, the compound possessing the carboxy moiety showed superior antiestrogen activity compared to ICI182,780 when dosed orally. Results of the pharmacokinctic evaluation indicated that the potent antiestrogen activity at oral dosing attributed to both the improved absorption from the intestinal wall and the metabolic stability of the compound in liver. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.090

文献信息

• Optically active chroman and thiochroman derivatives
  申请人：——

  公开号：US20030125571A1

  公开（公告）日：2003-07-03

  The present invention includes a compound having the following general formula (1): 1 in which X represents an oxygen atom or a sulfur atom, m represents an integer of 2 to 14, and n represents an integer of 2 to 7, or hydrates or pharmaceutically acceptable salts thereof. The compound of general formula (1) is advantageous in pharmaceutical use because of its far superior anti-estrogenic activity over the corresponding racemic mixture.

  本发明包括具有以下通式（1）的化合物：1式中，X代表氧原子或硫原子，m表示2到14的整数，n表示2到7的整数，或其水合物或药学上可接受的盐。通式（1）的化合物在制药应用中具有优越的抗雌激素活性，因为其比相应的外消旋混合物具有更好的效果。
• 3-methyl-chroman and -thiochroman derivatives
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US06552069B1

  公开（公告）日：2003-04-22

  The present invention provides a compound having the following general formula (1): in which R1 represents a hydrogen atom, etc.; R2 represents a C3-C3 perhalogenoalkyl group, etc.; each of R3 and R4 independently represents a hydrogen atom, etc.; X represents an oxygen atom or a sulfur atom; m represents an integer of 2 to 14; and n represents an integer of 0 to 8; or enantiomers of the compound, or hydrates or pharmaceutically acceptable salts of the compound or its enantiomers. The compound of general formula (1) is advantageous in pharmaceutical use because of its anti-estrogenic activity.

  本发明提供了具有以下一般式（1）的化合物：其中R1代表氢原子等；R2代表C3-C3全氟烷基等；R3和R4各自独立地代表氢原子等；X代表氧原子或硫原子；m表示2到14的整数；n表示0到8的整数；或该化合物的对映体、水合物或药学上可接受的盐。一般式（1）的化合物由于其抗雌激素活性在制药用途中具有优势。
• OPTICALLY ACTIVE CHROMAN AND THIOCHROMAN DERIVATIVES
  申请人：CHUGAI SEIYAKU KABUSHIKI KAISHA

  公开号：EP1241165A1

  公开（公告）日：2002-09-18

  The present invention includes a compound having the following general formula (1): in which Xrepresents an oxygen atom or a sulfur atom, mrepresents an integer of 2 to 14, and nrepresents an integer of 2 to 7, or hydrates or pharmaceutically acceptable salts thereof. The compound of general formula (1) is advantageous in pharmaceutical use because of its far superior anti-estrogenic activity over the corresponding racemic mixture.

  本发明包括具有以下通式(1)的化合物： 其中 X代表氧原子或硫原子、 m代表 2 至 14 的整数，和 n 代表 2 至 7 的整数、 或其水合物或药学上可接受的盐。通式（1）化合物的抗雌激素活性远远优于相应的外消旋混合物，因此在医药用途中具有优势。
• 3-METHYL-CHROMAN AND -THIOCHROMAN DERIVATIVES
  申请人：CHUGAI SEIYAKU KABUSHIKI KAISHA

  公开号：EP1241166A1

  公开（公告）日：2002-09-18

  The present invention provides a compound having the following general formula (1): in which    R1 represents a hydrogen atom, etc.;    R2 represents a C3-C5 perhalogenoalkyl group, etc.;    each of R3 and R4 independently represents a hydrogen atom, etc.;    X represents an oxygen atom or a sulfur atom;    m represents an integer of 2 to 14; and    n represents an integer of 0 to 8; or enantiomers of the compound, or hydrates or pharmaceutically acceptable salts of the compound or its enantiomers. The compound of general formula (1) is advantageous in pharmaceutical use because of its anti-estrogenic activity.

  本发明提供了具有以下通式(1)的化合物： 其中 R1 代表氢原子等 R2 代表 C3-C5 全卤代烷基等； R3 和 R4 各自独立地代表氢原子等； X 代表氧原子或硫原子； m 代表 2 至 14 的整数；以及 n 代表 0 至 8 的整数； 或该化合物的对映体，或该化合物或其对映体的水合物或药学上可接受的盐。通式（1）化合物具有抗雌激素活性，因此在医药用途中具有优势。
• US6552069B1
  申请人：——

  公开号：US6552069B1

  公开（公告）日：2003-04-22