2-oxo-3,3-trimethylenehept-5-ynephosphonic acid dimethyl ester | 89056-41-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: 2-oxo-3,3-trimethylenehept-5-ynephosphonic acid dimethyl ester
• 英文别名: Dimethyl {2-[1-(but-2-yn-1-yl)cyclobutyl]-2-oxoethyl}phosphonate；1-(1-but-2-ynylcyclobutyl)-2-dimethoxyphosphorylethanone
• CAS: 89056-41-7
• 化学式: C₁₂H₁₉O₄P
• 分子量: 258.254
• InChiKey: NYBITZJXYMNXTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  2-oxo-3,3-trimethylenehept-5-ynephosphonic acid dimethyl ester 在 sodium tetrahydroborate 、 sodium hydride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 溶剂黄146 为溶剂， 生成 2-{[2-((4S)-4-{(1E,3R)-3-[1-(2-butynyl)cyclobutyl]-3-hydroxy-1-propenyl}-2-oxo-1,3-oxazolidin-3-yl)ethyl]sulfanyl}-1,3-thiazole-4-carboxylic acid
  参考文献：
  名称：

  Discovery of highly potent dual EP 2 and EP 3 agonists with subtype selectivity

  摘要：

  The cyclic carbamate derivatives, 2-{[2-((4S)-4-{(1E,3R)-8-fluoro-3-hydroxy-4,4-dimethyl-1-octenyl}-2-oxo-1,3-oxazolidin-3-yl)ethyl]sulfanyl}-1,3-thiazole-4-carboxylic acid (5) and 2-{[2-((4S)-4-{(1E,3R)-3-[1-(4-fluorobutyl)cyclobutyl]-3-hydroxy-1-propenyl}-2-oxo-1,3-oxazolidin-3-yl)ethyl]sulfanyl}-1,3-thiazole-4-carboxylic acid (7) were identified as the first potent dual EP2 and EP3 agonists with selectivity against the EP1 and EP4 subtypes. Compounds 5 and 7 demonstrated highly potent dual EP2 and EP3 agonist activity with EC50 values of 10 nM or less. In addition, these compounds possess structural features distinct from natural prostaglandins, such as a cyclic carbamate moiety, a dimethyl or cyclobutyl group and a terminal fluorine atom. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.12.039
• 作为产物：
  描述：

  1-(2-丁炔-1-基)环丁烷羧酸 在 正丁基锂 、 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 生成 2-oxo-3,3-trimethylenehept-5-ynephosphonic acid dimethyl ester
  参考文献：
  名称：

  Discovery of highly potent dual EP 2 and EP 3 agonists with subtype selectivity

  摘要：

  The cyclic carbamate derivatives, 2-{[2-((4S)-4-{(1E,3R)-8-fluoro-3-hydroxy-4,4-dimethyl-1-octenyl}-2-oxo-1,3-oxazolidin-3-yl)ethyl]sulfanyl}-1,3-thiazole-4-carboxylic acid (5) and 2-{[2-((4S)-4-{(1E,3R)-3-[1-(4-fluorobutyl)cyclobutyl]-3-hydroxy-1-propenyl}-2-oxo-1,3-oxazolidin-3-yl)ethyl]sulfanyl}-1,3-thiazole-4-carboxylic acid (7) were identified as the first potent dual EP2 and EP3 agonists with selectivity against the EP1 and EP4 subtypes. Compounds 5 and 7 demonstrated highly potent dual EP2 and EP3 agonist activity with EC50 values of 10 nM or less. In addition, these compounds possess structural features distinct from natural prostaglandins, such as a cyclic carbamate moiety, a dimethyl or cyclobutyl group and a terminal fluorine atom. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.12.039

文献信息

• SKUBALLA, W.;RADUECHEL, B.;SCHWARZ, N.;VORBRUEGGEN, H.;CASALS-STENZEL, J.+
  作者：SKUBALLA, W.、RADUECHEL, B.、SCHWARZ, N.、VORBRUEGGEN, H.、CASALS-STENZEL, J.+

  DOI：——

  日期：——
• US5124343A
  申请人：——

  公开号：US5124343A

  公开（公告）日：1992-06-23
• Discovery of highly potent dual EP 2 and EP 3 agonists with subtype selectivity
  作者：Akihiro Kinoshita、Masato Higashino、Yoshiyuki Aratani、Akito Kakuuchi、Hidekazu Matsuya、Kazuyuki Ohmoto

  DOI：10.1016/j.bmcl.2015.12.039

  日期：2016.2

  The cyclic carbamate derivatives, 2-[2-((4S)-4-(1E,3R)-8-fluoro-3-hydroxy-4,4-dimethyl-1-octenyl}-2-oxo-1,3-oxazolidin-3-yl)ethyl]sulfanyl}-1,3-thiazole-4-carboxylic acid (5) and 2-[2-((4S)-4-(1E,3R)-3-[1-(4-fluorobutyl)cyclobutyl]-3-hydroxy-1-propenyl}-2-oxo-1,3-oxazolidin-3-yl)ethyl]sulfanyl}-1,3-thiazole-4-carboxylic acid (7) were identified as the first potent dual EP2 and EP3 agonists with selectivity against the EP1 and EP4 subtypes. Compounds 5 and 7 demonstrated highly potent dual EP2 and EP3 agonist activity with EC50 values of 10 nM or less. In addition, these compounds possess structural features distinct from natural prostaglandins, such as a cyclic carbamate moiety, a dimethyl or cyclobutyl group and a terminal fluorine atom. (C) 2015 Elsevier Ltd. All rights reserved.