methyl 1-(4-chloro-3-nitrophenyl)cyclopropanecarboxylate | 848846-84-4

• 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 1-(4-chloro-3-nitrophenyl)cyclopropanecarboxylate
• 英文别名: methyl 2-(4-chloro-3-nitrophenyl)cyclopropanoate；Methyl 1-(4-chloro-3-nitrophenyl)cyclopropane-1-carboxylate；methyl 1-(4-chloro-3-nitrophenyl)cyclopropane-1-carboxylate
• CAS: 848846-84-4
• 化学式: C₁₁H₁₀ClNO₄
• 分子量: 255.658
• InChiKey: UFAKFHAIZCUKOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 1-(4-chloro-3-nitrophenyl)cyclopropanecarboxylate 在 吡啶 、 20 % Pd(OH)2/C 、 氢气 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 乙酸乙酯 为溶剂， 反应 7.0h， 生成 1-{4-chloro-3-[(2,6-dimethyl-4-{[(2S)-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-2-yl]methoxy}benzoyl)amino]phenyl}cyclopropanecarboxylic acid
  参考文献：
  名称：

  Discovery of new orally active prostaglandin D2 receptor antagonists

  摘要：

  To identify an orally available drug candidate, a series of 3-benzoylaminophenylacetic acids were synthesized and evaluated as prostaglandin D-2 (PGD(2)) receptor antagonists. Some of the compounds tested were found to exhibit excellent inhibitory activity against cAMP accumulation in human platelet rich plasma (hPRP), which is one of the indexes of DP antagonism. The optimization process including improvement of the physicochemical properties such as solubility, which may result in an improved pharmacokinetic (PK) profile, is presented. Optimized compounds were studied for their pharmacokinetics and in vivo potential. A structure-activity relationship study is also presented. Some of the test compounds were found to have in vivo efficacy towards the inhibition of PGD(2)-induced and OVA-induced vascular permeability in guinea pig conjunctiva. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.08.065
• 作为产物：
  描述：

  1-(4-氯苯基)-1-环丙甲腈 在 氯化亚砜 、 硫酸 、 水 、 硝酸 作用下， 以 乙二醇二甲醚 为溶剂， 反应 11.0h， 生成 methyl 1-(4-chloro-3-nitrophenyl)cyclopropanecarboxylate
  参考文献：
  名称：

  Discovery of new orally active prostaglandin D2 receptor antagonists

  摘要：

  To identify an orally available drug candidate, a series of 3-benzoylaminophenylacetic acids were synthesized and evaluated as prostaglandin D-2 (PGD(2)) receptor antagonists. Some of the compounds tested were found to exhibit excellent inhibitory activity against cAMP accumulation in human platelet rich plasma (hPRP), which is one of the indexes of DP antagonism. The optimization process including improvement of the physicochemical properties such as solubility, which may result in an improved pharmacokinetic (PK) profile, is presented. Optimized compounds were studied for their pharmacokinetics and in vivo potential. A structure-activity relationship study is also presented. Some of the test compounds were found to have in vivo efficacy towards the inhibition of PGD(2)-induced and OVA-induced vascular permeability in guinea pig conjunctiva. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.08.065

文献信息

• CARBOXYLIC ACID COMPOUNDS AND MEDICINAL COMPOSITIONS CONTAINING THE SAME AS THE ACTIVE INGREDIENT
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP1666473B1

  公开（公告）日：2013-01-02
• Discovery of new orally active prostaglandin D2 receptor antagonists
  作者：Maki Iwahashi、Atsushi Naganawa、Atsushi Kinoshita、Atsushi Shimabukuro、Toshihiko Nishiyama、Seiji Ogawa、Yoko Matsunaga、Kohki Tsukamoto、Yutaka Okada、Ryoji Matsumoto、Fumio Nambu、Rie Oumi、Yoshihiko Odagaki、Jun Katagi、Koji Yano、Kousuke Tani、Hisao Nakai、Masaaki Toda

  DOI：10.1016/j.bmc.2011.08.065

  日期：2011.11

  To identify an orally available drug candidate, a series of 3-benzoylaminophenylacetic acids were synthesized and evaluated as prostaglandin D-2 (PGD(2)) receptor antagonists. Some of the compounds tested were found to exhibit excellent inhibitory activity against cAMP accumulation in human platelet rich plasma (hPRP), which is one of the indexes of DP antagonism. The optimization process including improvement of the physicochemical properties such as solubility, which may result in an improved pharmacokinetic (PK) profile, is presented. Optimized compounds were studied for their pharmacokinetics and in vivo potential. A structure-activity relationship study is also presented. Some of the test compounds were found to have in vivo efficacy towards the inhibition of PGD(2)-induced and OVA-induced vascular permeability in guinea pig conjunctiva. (C) 2011 Elsevier Ltd. All rights reserved.