methyl <1S-<1α,2α(Z),3α,4α>>-7-<3-<(tosyloxy)methyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptanoate | 107437-25-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl <1S-<1α,2α(Z),3α,4α>>-7-<3-<(tosyloxy)methyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptanoate
• 英文别名: [1β,2α(Z),3β,4β]-7-[3-(p-Toluenesulfonyloxymethyl)-7-oxabicyclo[2.2.1]hept-2-yl]-5-heptenoic acid, methyl ester；methyl [1S-(1α,2α(Z),3α,4α)]-7-{3-[(tosyloxy)methyl]-7-oxabicyclo[2.2.1]hept-2-yl}-5-heptanoate；methyl (Z)-7-[(1S,2R,3R,4R)-3-[(4-methylphenyl)sulfonyloxymethyl]-7-oxabicyclo[2.2.1]heptan-2-yl]hept-5-enoate
• CAS: 107437-25-2
• 化学式: C₂₂H₃₀O₆S
• 分子量: 422.543
• InChiKey: ACQHIDOADVDBSX-MIWKIQGNSA-N

物化性质

• 熔点：
  68-70 °C
• 沸点：
  549.7±30.0 °C(Predicted)
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.78
• 重原子数：
  29.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl <1S-<1α,2α(Z),3α,4α>>-7-<3-<(tosyloxy)methyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptanoate 在 lithium hydroxide 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.5h， 生成 <1α,2α(Z),3α,4α>-(+/-)-7-<3-<<(3-Phenylpropyl)thio>methyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoic acid
  参考文献：
  名称：

  9,11-Epoxy-9-homo-14-thiaprost-5-enoic acid derivatives: potent thromboxane A2 antagonists

  摘要：

  A novel bicyclic prostaglandin analogue, (1S)-[1 alpha,2 alpha(Z),3 alpha,4 alpha]-7-[3-[(hexylthio)methyl]-7- oxabicyclo [2.2.1]hept-2-yl]-5-heptenoic acid ((-)-10), and its cogeners were found to be potent antagonists at the TxA2 receptor. Compound (-)-10 was the only stereoisomer out of eight possible structures that was active. Thioether (-)-10 was 30-40-fold more potent than another TxA2 antagonist, BM 13.177, in inhibiting arachidonic acid (AA) induced aggregation of human platelet-rich plasma. Compound (-)-10 was effective (I50 = 0.5 +/- 0.4 microM) in inhibiting 9,11-azo-PGH2-induced (0.1 microgram/mL) contraction of guinea pig tracheal spirals. The bronchoconstriction in anesthetized guinea pigs induced by AA was also effectively antagonized by (-)-10 (1 mg/kg, iv); however, in this assay (-)-10 exhibited some direct agonist activity. Radioligand binding studies in washed (human) platelets revealed that (-)-10 is one of the most potent ligands for the PGH2/TxA2 receptor yet described (Kd = 1.6 +/- 0.4 nM).

  DOI：

  10.1021/jm00125a009
• 作为产物：
  描述：

  [1S-[1α,2α(5Z),3α,4α]]-7-[3-(hydroxymethyl)-7-oxabicyclo[2.2.1]hept-2-yl]-5-heptenoic acid, methyl ester 以74的产率得到methyl <1S-<1α,2α(Z),3α,4α>>-7-<3-<(tosyloxy)methyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptanoate
  参考文献：
  名称：

  J. Med. Chem. 1990, 33, 2465-2476

  摘要：

  DOI：

文献信息

• 7-Oxabicyclo[2.2.1]heptyl carboxylic acids as thromboxane A2 antagonists: aza .omega.-chain analogs
  作者：Masami Nakane、Joyce A. Reid、Wen Ching Han、Jagabandhu Das、Vu Chi Truc、Martin F. Haslanger、Dianne Garber、Don N. Harris、Anders Hedberg、Martin L. Ogletree、Steven E. Hall

  DOI：10.1021/jm00171a021

  日期：1990.9.1

  A novel bicyclic prostaglandin analogue, [1S-[1 alpha, 2 alpha (Z), 3 alpha, 4 alpha]]-7-[3-[[[[(1- Oxoheptyl)amino]acetyl]amino]-methyl]-7-oxabicyclo[2.2.1]hept-2- yl]-5-heptenoic acid [-)-7) was found to be a potent and selective thromboxane A2 (TxA2) receptor antagonist. Unlike the related series of omega-chain allylic alcohols, amide 7 and its congeners were uniformly free of direct contractile

  新型的双环前列腺素类似物，[1S- [1 alpha，2 alpha（Z），3 alpha，4 alpha]]-7- [3-[[[[[（[Oxoheptyl）amino] acetyl] amino] -methyl]发现-7-氧杂双环[2.2.1]庚-2-基] -5-庚烯酸[-]-7是有效的选择性血栓烷A2（TxA2）受体拮抗剂。与相关系列的ω-链烯丙基醇不同，酰胺7及其同类物在体外（牛冠状动脉）和体内（麻醉的豚鼠）均一致没有直接收缩活性。酰胺7有效抑制（a）花生四烯酸诱导的人血小板丰富血浆的血小板聚集（I50 = 0.18 +/- 0.006 microM），（b）11,9-环氧甲氧基-PGH2诱导的人血小板血小板聚集-血浆（I50 = 0.24 microM），（c）11,9-环氧甲氧基-PGH2诱导的豚鼠气管（Kb = 3.0 +/- 0.3 nM）或大鼠主动脉（Kb = 8.8 +/-
• 7-oxabicycloheptane substituted thio prostaglandin analogs useful in the
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04607049A1

  公开（公告）日：1986-08-19

  7-Oxabicycloheptane substituted thio prostaglandin analogs are provided having the structural formula ##STR1## wherein R is hydrogen, lower alkyl, alkali metal, or a polyhydroxylamine salt, R.sup.1 is hydrogen, lower alkyl, arylalkyl, aryl, cycloalkyl or cycloalkylalkyl, R.sup.2 is hydrogen or lower alkyl, A is --CH.dbd.CH-- or --(CH.sub.2).sub.2, n is 1 to 4, n' is 0, 1 or 2, q is 1 to 10 and m is 0 to 8, and including all stereoisomers thereof. The compounds are cardiovascular agents useful, for example, in the treatment of thrombotic disease, and as such are useful in inhibiting platelet aggregation.

  提供了7-Oxabicycloheptane取代硫代前列腺素类似物，其结构式为##STR1##其中R为氢，低碳基，碱金属或多羟胺盐，R.sup.1为氢，低碳基，芳基烷基，芳基，环烷基或环烷基烷基，R.sup.2为氢或低碳基，A为--CH.dbd.CH--或--(CH.sub.2).sub.2，n为1到4，n'为0、1或2，q为1到10，m为0到8，包括所有立体异构体。这些化合物是心血管药物，例如在治疗血栓性疾病方面有用，因此在抑制血小板聚集方面有用。
• 7-Oxabicycloheptane substituted thio prostaglandin analogs and their use
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04555523A1

  公开（公告）日：1985-11-26

  7-Oxabicycloheptane substituted thio prostaglandin analogs are provided having the structural formula ##STR1## wherein R is hydrogen, lower alkyl or alkali metal, R.sup.1 is lower alkyl, arylalkyl, aryl, cycloalkyl or cycloalkylalkyl, X is O, S or NH, A is --CH.dbd.CH-- or --(CH.sub.2).sub.2, p is 0 to 4, n is 1 to 4, n' is 0 to 2, q is 1 to 4 and m is 0 to 8, and including all stereoisomers thereof. The compounds are cardiovascular agents useful, for example, in the treatment of thrombolytic disease; and are antiinflammatory agents useful, for example, in the treatment of rheumatoid arthritis.

  提供了7-Oxabicycloheptane取代硫代前列腺素类似物，其结构式为##STR1##其中R为氢、较低烷基或碱金属，R.sup.1为较低烷基、芳基烷基、芳基、环烷基或环烷基烷基，X为O、S或NH，A为--CH.dbd.CH--或--(CH.sub.2).sub.2，p为0到4，n为1到4，n'为0到2，q为1到4，m为0到8，包括所有立体异构体。这些化合物是心血管药物，例如在治疗溶栓病方面有用；并且是抗炎药物，例如在治疗类风湿关节炎方面有用。
• J. Med. Chem. 1989, 32, 974-984
  作者：

  DOI：——

  日期：——
• NAKANE, MASARNI;REID, JOYCE A.;HAN, WEN-CHING;DAS, JAGABANDHU;TRUC, VU CH+, J. MED. CHEM., 33,(1990) N, C. 2465-2476
  作者：NAKANE, MASARNI、REID, JOYCE A.、HAN, WEN-CHING、DAS, JAGABANDHU、TRUC, VU CH+

  DOI：——

  日期：——