4-(phenoxycarbonylamino)benzoic acid | 22564-49-4

• 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: 4-(phenoxycarbonylamino)benzoic acid
• CAS: 22564-49-4
• 化学式: C₁₄H₁₁NO₄
• mdl: MFCD00522709
• 分子量: 257.246
• InChiKey: VIMFAZIYCUICPH-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C
• 沸点：
  420.8±37.0 °C(Predicted)
• 密度：
  1.376±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(phenoxycarbonylamino)benzoic acid 在 硫酸 、 盐酸羟胺 、 sodium 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 N-hydroxy-4-(3-phenethylureido)benzamide
  参考文献：
  名称：

  Design, synthesis and in vitro evaluation of amidoximes as histone deacetylase inhibitors for cancer therapy

  摘要：

  Amindoximes are geometric isomers of N-hydroxyamidines which are bioisosteres of hydroxamates. Since amindoxime group is capable of chelating transition metal ions including zinc ion, amindoximes should possess histone deacetylases (HDACs) inhibitory activity. In this work, we designed and synthesized a series of amindoximes, examined their inhibitory activities against HDACs, and investigated their cytotoxicity to human cancer cells. Preliminary results demonstrated that amindoximes possessed submicromolar HDACs inhibitory activity, with noteworthy enhancement compared with hydroxamates. Furthermore, the amindoximes arrested HCT116 and A549 cells in G2/M phase and showed good efficacy in inducing cells death. We provided a proof-of-concept that amindoximes could be used as HDACs inhibitors and hold great promise as epigenetic drugs. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.08.073
• 作为产物：
  描述：

  4-异氰酰基苯甲酸甲酯 在 吡啶 、 盐酸 作用下， 以 溶剂黄146 为溶剂， 生成 4-(phenoxycarbonylamino)benzoic acid
  参考文献：
  名称：

  460.细胞毒性化合物。第二部分 一些“氮芥”型酰胺

  摘要：

  DOI：

  10.1039/jr9610002365

文献信息

• [EN] DELIVERY OF THERAPEUTIC ALKALOID COMPOUNDS<br/>[FR] ADMINISTRATION DE COMPOSÉS ALCALOÏDES THÉRAPEUTIQUES
  申请人：SENSORIUM THERAPEUTICS INC

  公开号：WO2023076586A1

  公开（公告）日：2023-05-04

  Disclosed are prodrug compounds that can be converted to mesembrine under biologically relevant conditions, such as hydrolysis in vivo; and related methods of preparing and using these compounds. Stable preparations of isolated mesembrine stereoisomers are also provided.

  所公开的是可在生物相关条件下（如体内水解）转化为美森布林的原药化合物，以及制备和使用这些化合物的相关方法。此外，还提供了分离出的间苯三酚立体异构体的稳定制备方法。
• Über die Herstellung von Isocyanatocarbonsäure-trimethylsilylestern
  作者：Hans R. KRICHELDORF

  DOI：10.1055/s-1970-21656

  日期：——
• Synthesis of N-aryl and N-arylcarbamoylamino derivatives of 1,3-diazinane-5-carboxamide and their activity against glioblastoma LN-229 cell line
  作者：Rebecca J. Hron、Branko S. Jursic、Donna M. Neumann

  DOI：10.1016/j.bmc.2016.09.074

  日期：2016.12

  Six structural motifs based on the initial (lead) structure of merbarone were designed, prepared, and tested against the glioblastoma LN-229 cell line. Three different structural moieties were modified in the search for optimal glioblastoma activity: the 1,3-diazinane moiety, the aryl moiety, and the heteroatom linker. Calculated molecular descriptors such as lipophilicity (ClogP), acidic strength (calculated pK(a)), and polar surface area (PSA) were used to design a diverse structural library of these compounds. From six different structural motifs and 136 compounds, a handful of examples with moderate (100 mu g/ml), good (10 mu g/ml) and excellent (1 mu g/ml) glioblastoma activity were elucidated. (C) 2016 Published by Elsevier Ltd.
• 1,3-Disubstituted benzazepines as neuropeptide Y Y1 receptor antagonists
  作者：Yasushi Murakami、Sanji Hagishita、Tetsuo Okada、Makoto Kii、Hiroshi Hashizume、Tatsuroh Yagami、Masafumi Fujimoto

  DOI：10.1016/s0968-0896(99)00087-5

  日期：1999.8

  A nuclei, have been designed, synthesized, and evaluated for activity. Through a blind screening we found the compound 1-N-(3-(N'-(tert-butoxycarbonyl)amino)benzyl)-7-methoxy-(3-(3)-methylureido)-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one (9: IC50 = 1.6 mu M). Chemical modifications of 9 gave a potent NPY Y1 antagonist 3-(N-(4-hydroxyphenyl)-N'-methylguanidino)-1-N-(3-(N'-(tert-butoxycarbonyl)amino)benzyl)-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one (14c: IC50 = 43 nM), which had no affinity for NPY Y2 and Y5 receptors. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Design, synthesis and in vitro evaluation of amidoximes as histone deacetylase inhibitors for cancer therapy
  作者：Peifu Jiao、Peng Jin、Chencan Li、Lechao Cui、Lihua Dong、Bin Pan、Wentong Song、Liang Ma、Jinlong Dong、Lei Song、Xinjie Jin、Faming Li、Maosheng Wan、Zhitao Lv、Qiaohong Geng

  DOI：10.1016/j.bmcl.2016.08.073

  日期：2016.10

  Amindoximes are geometric isomers of N-hydroxyamidines which are bioisosteres of hydroxamates. Since amindoxime group is capable of chelating transition metal ions including zinc ion, amindoximes should possess histone deacetylases (HDACs) inhibitory activity. In this work, we designed and synthesized a series of amindoximes, examined their inhibitory activities against HDACs, and investigated their cytotoxicity to human cancer cells. Preliminary results demonstrated that amindoximes possessed submicromolar HDACs inhibitory activity, with noteworthy enhancement compared with hydroxamates. Furthermore, the amindoximes arrested HCT116 and A549 cells in G2/M phase and showed good efficacy in inducing cells death. We provided a proof-of-concept that amindoximes could be used as HDACs inhibitors and hold great promise as epigenetic drugs. (C) 2016 Elsevier Ltd. All rights reserved.