methyl 5(Z)-7-[(1S,2S,3S,5R)-3-amino-6,6-dimethylbicyclo[3.1.1]hept-2-yl]-5-heptenoate | 82402-56-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl 5(Z)-7-[(1S,2S,3S,5R)-3-amino-6,6-dimethylbicyclo[3.1.1]hept-2-yl]-5-heptenoate
• 英文别名: 7-[(1S,2S,3S,5R)-3-amino-6,6-dimethylbicyclo[3.1.1]heptan-2-yl]-5Z-heptenoic acid methyl ester；(5Z)-6-[(1S,2S,3S,5R)-3-aminopinan-10-yl]hex-5-enoic acid methyl ester；methyl (Z)-7-[(1S,2S,3S,5R)-3-amino-6,6-dimethyl-2-bicyclo[3.1.1]heptanyl]hept-5-enoate
• CAS: 82402-56-0
• 化学式: C₁₇H₂₉NO₂
• 分子量: 279.423
• InChiKey: KTOCDLYDWXQNEX-JVRCYIESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 5(Z)-7-[(1S,2S,3S,5R)-3-amino-6,6-dimethylbicyclo[3.1.1]hept-2-yl]-5-heptenoate 生成 (Z)-7-[(1S,2S,3S,5R)-3-[[(2R)-2-hydroxy-3-phenylpropanoyl]amino]-6,6-dimethyl-2-bicyclo[3.1.1]heptanyl]hept-5-enoic acid
  参考文献：
  名称：

  MIYAKE, HAJIMU;OKEGAWA, TADAO;KAWASAKI, AKIYOSHI

  摘要：

  DOI：

文献信息

• Carbocyclic sulfonamides
  申请人：Ono Pharmaceutical Co., Ltd.

  公开号：US05663417A1

  公开（公告）日：1997-09-02

  (1) Prostaglandin (PG) E.sub.2 antagonist or agonist containing carbocyclic sulfonamides represented by the compound of the formula (I): ##STR1## cyclodextrin clathrates thereof, non-toxic salts thereof as active ingredient, (2) carbocyclic sulfonamides represented by the compound of the formula (II): ##STR2## cyclodextrin clathrates thereof, non-toxic salts thereof, (3) process for the preparation of the compound represented by the compound of the formula (II) described hereinbefore, (4) PGE.sub.2 antagonist or agonist containing the compound represented by the compound of the formula (II) as active ingredient. The compounds represented by the compounds of the formula (I) and (II) can be adapted to medicines which possess an inhibitory effect of uterine contraction, an analgetic action, an inhibitory effect of digestive peristalsis, a sleep-inducing effect as PGE.sub.2 antagonists, and an uterine contractile activity, a promoting effect of digestive peristalsis, a suppressive effect of gastric acid secretion, a hypotensive activity as PGE.sub.2 agonists, because they bind onto PGE.sub.2 receptor and have an activity of antagonist or agonist against the action thereof.

  (1) 包含化合物(I)所代表的环状磺酰胺的前列腺素(PG)E.sub.2拮抗剂或激动剂，其化合物为：##STR1## 其环状糖囊复合物和非毒性盐为活性成分。(2) 包含化合物(II)所代表的环状磺酰胺的化合物，其化合物为：##STR2## 其环状糖囊复合物和非毒性盐为活性成分。(3) 描述了制备化合物(II)所代表的化合物的方法。(4) 包含化合物(II)所代表的化合物作为活性成分的PGE.sub.2拮抗剂或激动剂。化合物(I)和(II)所代表的化合物可以用于具有抑制子宫收缩、镇痛作用、抑制消化蠕动、诱导睡眠作用的药物，作为PGE.sub.2拮抗剂，也可以用于具有子宫收缩活性、促进消化蠕动、抑制胃酸分泌、降压作用的药物，作为PGE.sub.2激动剂，因为它们能够结合到PGE.sub.2受体并具有其作用的拮抗剂或激动剂活性。
• 13-Aza-14-oxo-txa2 analogues
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP0171146A1

  公开（公告）日：1986-02-12

  A novel 13-aza-14-oxo-TXA2 analogue of general formula: [wherein symbol A represents (i) a group of general formula: -CH2CH2-(CH2)m-, (ii)) a group of general formula: cis-CH=CH-(CH2)17, (iii) a group of general formula: -CH2O-(CH2)m-, (iv) a group of general formula: -S-(CH2)m-(wherein m represents an integer of from 1 to 6) or (v) a group of general formula: - R1 represents a hydrogen atom or a straight or branched alkyl group of from 1 to 12 carbon atom(s); R2 represents a bond or a straight or branched alkylene or alkylene group of from 1 to 10 carbon atom(s) unsubstituted or substituted by at least one of hydroxy group, amino group, halogen atom or phenylthio group; R3 represents (i) a phenyl, phenoxy or phenylthio group unsubstituted or substituted by at least one of straight or branched alkyl or alkoxy group of from 1 to 6 carbon atom(s), halogen atom or hydroxy group, (ii) a straight or branched alkyl, alkenyl or alkynyl group of from 1 to 6 carbon atom(s) unsubstituted or substituted by at least one of halogen atom or hydroxy group, (iii) a cycloalkyl, cycloalkyloxy or cycloalkylthio group of from 4 to 7 carbon atoms unsubstituted or substituted by at least one of straight or branched alkyl group of from 1 to 6 carbon atom(s), halogen atom or hydroxy group, (iv) a naphthyl, indolyl or indanyl group, or (v) an amino group unsubstituted or substituted by at least one of straight or branched alkyl group of from 1 to 6 carbon atom(s); and R4 represents a hydrogen atom or a methyl group. With proviso that, the carbon atom neighbored with R3 in R2 should have no substituents, when R3 represents a phenyloxy, phenylthio, cycloalkyloxy or cycloalkylthio group unsubstituted or substituted.] and cyclodextrin clathrates thereof and non-toxic salts thereof wherein R' represents a hydrogen atom possess an antagonistic activity on TXA2, in particular, inhibit blood platelet aggregation and contraction of artery, and are, therefore, useful for prevention and/or treatment of inflammation, hypertension, thrombus, cerebral apoplexy, asthma, cardiac infarction, angina pectoris, cerebral infarction and death by acute cardiac diseases in mammals, in particular in humans, which are induced by thromboxane A2.

  一种通式为 13-aza-14-oxo-TXA2 的新型类似物： [其中符号 A 代表 (i) 通式中的基团-CH2CH2-(CH2)m-、 (ii) 通式为：顺式-CH=CH-(CH2)17 的基团、 (iii) 通式为-CH2O-(CH2)m-、 (iv) 通式为-S-(CH2)m-(其中 m 代表 1 至 6 的整数)或 (v) 通式为- R1 代表氢原子或 1 至 12 个碳原子的直链或支链烷基； R2 代表未取代的或被羟基、氨基、卤素原子或苯硫基中的至少一个取代的键或 1 至 10 个碳原子的直链或支链亚烷基或亚烷基； R3 代表 (i) 未被 1 至 6 个碳原子的直链或支链烷基或烷氧基、卤素原子或羟基中的 至少一个取代的苯基、苯氧基或苯硫基、 (ii) 1 至 6 个碳原子的直链或支链烷基、烯基或炔基，未被卤素原子或羟基中的 至少一个取代或被取代、 (iii) 4 至 7 个碳原子的环烷基、环烷氧基或环烷基硫代基团，未被 1 至 6 个碳原子的直链或支链烷基、卤素原子或羟基中的至少一个取代或被其取代、 (iv) 萘基、吲哚基或茚基，或 (v) 未被取代或被至少一个 1 至 6 个碳原子的直链或支链烷基取代的氨基； 以及 R4 代表氢原子或甲基。 但 R3 代表未取代或取代的苯氧基、苯硫基、环烷氧基或环烷基硫基时，R2 中与 R3 相邻的碳原子应无取代基。］ 及其环糊精包合物和无毒盐，其中 R' 代表氢原子，具有拮抗 TXA2 的活性，特别是抑制血小板聚集和动脉收缩，因此、可用于预防和/或治疗由血栓素 A2 引起的哺乳动物，特别是人类的炎症、高血压、血栓、脑中风、哮喘、心肌梗塞、心绞痛、脑梗塞和急性心脏病引起的死亡。
• Bicyclic sulfonamide derivatives
  申请人：SHIONOGI & CO., LTD.

  公开号：EP0226346A1

  公开（公告）日：1987-06-24

  Bicyclic sulfonamido derivatives represented by the formula: wherein R, is a hydrogen or lower alkyl; R2 is alkyl, substituted or unsubstituted aryl, aralkyl or heterocycle; R3 is hydrogen or methyl; X is an alkylene or alkenylene which may be substituted by a fluorine atom or atoms and may contain a oxygen, sulfur and/or phenylene in the chain; Y is straight or branched alkylene or alkeneylene, oxygen, or sulfur; m is 0 or 1; and n is 0, 1 or 2, or salts thereof, the compounds being of use as antithrombotic, anti-vasoconstricting, and anti-bronchoconstricting drugs.

  由式表示的双环磺酰胺基衍生物： 其中 R 是氢或低级烷基；R2 是烷基、取代或未取代的芳基、芳烷基或杂环；R3 是氢或甲基；X 是亚烷基或烯基，可被一个或多个氟原子取代，链中可含有氧、硫和/或亚苯基；Y 是直链或支链亚烷基或亚烷基、氧或硫；m 是 0 或 1；n 是 0、1 或 2 或其盐，这些化合物可用作抗血栓、抗血管收缩和抗支气管收缩药物。
• Carbocyclic sulfonamides as agonists or antagonists of PGEZ
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP0608847A1

  公开（公告）日：1994-08-03

  (1) Prostaglandin (PG) E₂ antagonist or agonist containing carbocyclic sulfonamides represented by the compound of the formula (I): cyclodextrin clathrates thereof, non-toxic salts thereof as active ingredient,    (2) carbocyclic sulfonamides represented by the compound of the formula (II): cyclodextrin clathrates thereof, non-toxic salts thereof,    (3) process for the preparation of the compound represented by the compound of the formula (II) described hereinbefore,    (4) PGE₂ antagonist or agonist containing the compound represented by the compound of the formula (II) as active ingredient. The compounds represented by the compounds of the formula (I) and (II) can be adapted to medicines which possess an inhibitory effect of uterine contraction, an analgetic action, an inhibitory effect of digestive peristalsis, a sleep-inducing effect as PGE₂ antagonists, and an uterine contractile activity, a promaoting effect of digestive peristalsis, a suppressive effect of gastric acid secretion, a hypotensive activity as PGE₂ agonists, because they bind onto PGE₂ receptor and have an activity of antagonist or agonist against the action thereof.

  (1) 以式(I)化合物为代表的前列腺素(PG)E₂拮抗剂或激动剂： 以其环糊精凝块、无毒盐类为活性成分、 (2) 以式（II）化合物为代表的碳环磺胺类化合物： 其环糊精凝块、其无毒盐、 (3) 前述以式(II)化合物为代表的化合物的制备工艺、 (4) 以式(II)化合物为有效成分的 PGE₂拮抗剂或激动剂。 以式（I）和（II）化合物为代表的化合物可作为 PGE ₂拮抗剂适用于具有子宫收缩抑制作用、镇痛作用、消化道蠕动抑制作用、睡眠诱导作用和子宫收缩活性的药物、以及作为 PGE ₂激动剂的子宫收缩活性、促进消化道蠕动的作用、抑制胃酸分泌的作用、降血压活性，因为它们与 PGE ₂受体结合，并对其作用具有拮抗剂或激动剂的活性。
• Novel synthesis and biochemical properties of an [125I]-labeled photoaffinity probe for thromboxane A2/prostaglandin H2 receptors
  作者：Dale E. Mais、Nancy L. Bowling、Timothy A. True、Masao Naka、Thomas A. Morinelli、John E. Oatis、Nobuyuki Hamanaka、Perry V. Halushka

  DOI：10.1021/jm00108a042

  日期：1991.4