2-[cyclohexyl(methyl)carbamoyl]benzoic acid | 735342-69-5

• 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: 2-[cyclohexyl(methyl)carbamoyl]benzoic acid
• CAS: 735342-69-5
• 化学式: C₁₅H₁₉NO₃
• 分子量: 261.321
• InChiKey: VWCGBSLMTUMNKU-UHFFFAOYSA-N

物化性质

• 沸点：
  461.0±28.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[cyclohexyl(methyl)carbamoyl]benzoic acid 、 (3-exo)-8-[(6-fluoro-2-naphthyl)methyl]-8-azabicyclo[3.2.1]octan-3-amine dihydrochloride 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-cyclohexyl-N'-{(3-exo)-8-[(6-fluoro-2-naphthyl)-methyl]-8-azabicyclo[3.2.1]oct-3-yl}-N-methylphthalamide
  参考文献：
  名称：

  Design and synthesis of 6-fluoro-2-naphthyl derivatives as novel CCR3 antagonists with reduced CYP2D6 inhibition

  摘要：

  In our previous study on discovering novel types of CCR3 antagonists, we found a fluoronaphthalene derivative (1) that exhibited potent CCR3 inhibitory activity with an IC(50) value of 20 nM. However, compound 1 also inhibited human cytochrome P450 2D6 (CYP2D6) with an IC(50) value of 400 nM. In order to reduce its CYP2D6 inhibitory activity, we performed further systematic structural modi. cations on 1. In particular, we focused on reducing the number of lipophilic moieties in the biphenyl part of 1, using Clog D(7.4) values as the reference index of lipophilicity. This research led to the identification of N-{(3-exo)-8-[(6-fluoro-2-naphthyl)methyl]-8-azabicyclo[3.2.1]oct-3-yl}-3-(piperidin-1-ylcarbonyl)isonicotinamide 1-oxide (30) which showed comparable CCR3 inhibitory activity (IC(50) = 23 nM) with much reduced CYP2D6 inhibitory activity (IC50 = 29,000 nM) compared with 1. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.006
• 作为产物：
  描述：

  苯酐 、 N-甲基环己胺 以 四氢呋喃 为溶剂， 反应 15.5h， 以76%的产率得到2-[cyclohexyl(methyl)carbamoyl]benzoic acid
  参考文献：
  名称：

  Design and synthesis of 6-fluoro-2-naphthyl derivatives as novel CCR3 antagonists with reduced CYP2D6 inhibition

  摘要：

  In our previous study on discovering novel types of CCR3 antagonists, we found a fluoronaphthalene derivative (1) that exhibited potent CCR3 inhibitory activity with an IC(50) value of 20 nM. However, compound 1 also inhibited human cytochrome P450 2D6 (CYP2D6) with an IC(50) value of 400 nM. In order to reduce its CYP2D6 inhibitory activity, we performed further systematic structural modi. cations on 1. In particular, we focused on reducing the number of lipophilic moieties in the biphenyl part of 1, using Clog D(7.4) values as the reference index of lipophilicity. This research led to the identification of N-{(3-exo)-8-[(6-fluoro-2-naphthyl)methyl]-8-azabicyclo[3.2.1]oct-3-yl}-3-(piperidin-1-ylcarbonyl)isonicotinamide 1-oxide (30) which showed comparable CCR3 inhibitory activity (IC(50) = 23 nM) with much reduced CYP2D6 inhibitory activity (IC50 = 29,000 nM) compared with 1. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.006

文献信息

• [EN] PHOTOSENSITIVE RESIN COMPOSITION, CURED FILM, LAMINATE, METHOD FOR PRODUCING CURED FILM, AND SEMICONDUCTOR DEVICE<br/>[FR] COMPOSITION DE RÉSINE PHOTOSENSIBLE, FILM DURCI, STRATIFIÉ, PROCÉDÉ DE PRODUCTION DE FILM DURCI, ET DISPOSITIF À SEMI-CONDUCTEUR<br/>[JA] 感光性樹脂組成物、硬化膜、積層体、硬化膜の製造方法、および半導体デバイス
  申请人：FUJIFILM CORP

  公开号：WO2020054226A1

  公开（公告）日：2020-03-19

  熱塩基発生剤は式（Ｎ１）で表される。感光性樹脂組成物は、熱塩基発生剤と複素環含有ポリマーの前駆体とを含む。 式（Ｎ１）中、ＲN1およびＲN2はそれぞれ独立に１価の有機基を表し、ＲC1は水素原子または保護基を表し、Ｌは２価の連結基を表す。硬化膜は、感光性樹脂組成物を硬化してなる。積層体は、硬化膜を２層以上有し、硬化膜の間に金属層を有する。硬化膜の製造方法は、感光性樹脂組成物を基板に適用して膜を形成する膜形成工程を含む。半導体デバイスは、硬化膜または積層体を有する。
• Design and synthesis of 6-fluoro-2-naphthyl derivatives as novel CCR3 antagonists with reduced CYP2D6 inhibition
  作者：Ippei Sato、Koichiro Morihira、Hiroshi Inami、Hirokazu Kubota、Tatsuaki Morokata、Keiko Suzuki、Yosuke Iura、Aiko Nitta、Takayuki Imaoka、Toshiya Takahashi、Makoto Takeuchi、Mitsuaki Ohta、Shin-ichi Tsukamoto

  DOI：10.1016/j.bmc.2008.08.006

  日期：2008.9

  In our previous study on discovering novel types of CCR3 antagonists, we found a fluoronaphthalene derivative (1) that exhibited potent CCR3 inhibitory activity with an IC(50) value of 20 nM. However, compound 1 also inhibited human cytochrome P450 2D6 (CYP2D6) with an IC(50) value of 400 nM. In order to reduce its CYP2D6 inhibitory activity, we performed further systematic structural modi. cations on 1. In particular, we focused on reducing the number of lipophilic moieties in the biphenyl part of 1, using Clog D(7.4) values as the reference index of lipophilicity. This research led to the identification of N-(3-exo)-8-[(6-fluoro-2-naphthyl)methyl]-8-azabicyclo[3.2.1]oct-3-yl}-3-(piperidin-1-ylcarbonyl)isonicotinamide 1-oxide (30) which showed comparable CCR3 inhibitory activity (IC(50) = 23 nM) with much reduced CYP2D6 inhibitory activity (IC50 = 29,000 nM) compared with 1. (C) 2008 Elsevier Ltd. All rights reserved.