4-[2-(5-chloro-2-methoxybenzamido)-ethyl]-phenylacetic acid | 62910-22-9

• 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-[2-(5-chloro-2-methoxybenzamido)-ethyl]-phenylacetic acid
• 英文别名: 2-[4-[2-[(5-chloro-2-methoxybenzoyl)amino]ethyl]phenyl]acetic acid
• CAS: 62910-22-9
• 化学式: C₁₈H₁₈ClNO₄
• 分子量: 347.798
• InChiKey: JPPXVKFDEFETOG-UHFFFAOYSA-N

物化性质

• 沸点：
  547.2±50.0 °C(Predicted)
• 密度：
  1.286±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 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-(2-<5-chloro-2-methoxy-benzamido>-ethyl)-acetophenone 、 4-[2-(5-chloro-2-methoxybenzamido)-ethyl]-phenylacetic acid 在 氢氧化钾 、 potassium permanganate 作用下， 以 水 为溶剂， 生成 4-[2-(5-chloro-2-methoxybenzamido)-ethyl]-phenylglyoxylic acid
  参考文献：
  名称：

  Hypoglycaemically and hypolipidaemically active derivatives of

  摘要：

  Phenylacetic acid derivatives of the formula ##STR1## wherein A is an aryl radical optionally substituted by halogen, trifluoromethyl, alkyl, alkoxy, alkenyloxy, alkoxyalkoxy, alkyl-substituted amino or aryloxy, or a heterocyclic ring system optionally substituted by halogen, alkyl or alkoxy, Y is a valency bond or an optionally branched alkylene radical containing up to 3 carbon atoms, and R.sub.1 and R.sub.2 each independently is hydrogen or a lower alkyl radical, or a physiologically compatible salt or ester thereof, exhibit marked hypoglycaemic and hypolipidaemic activity.

  公开号：

  US04207341A1
• 作为产物：
  描述：

  Ethyl 4-[2-(5-chloro-2-methoxybenzamido)-ethyl]-phenylacetate 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 4-[2-(5-chloro-2-methoxybenzamido)-ethyl]-phenylacetic acid
  参考文献：
  名称：

  Preparation of phenylethylbenzamide derivatives as modulators of DNMT3 activity

  摘要：

  DNA甲基转移酶（DNMTs）是一类表观遗传酶，能催化将甲基供体S-腺苷-L-甲硫氨酸上的甲基基团转移到DNA中胞嘧啶的C5位置上。这一过程在癌症中发生失调，导致肿瘤抑制基因的高甲基化和沉默。开发强效且特异的DNMT抑制剂对于发现新的癌症治疗方法至关重要。本文报告了29种源自NSC 319745的类似物的合成及其DNMT抑制活性。使用发光甲基化测定法评估了选定化合物在人乳腺癌细胞系MDA-MB-231中对甲基化水平的影响。进行了分子对接研究，以提出该系列化合物的结合模式。

  DOI：

  10.1039/c3md00214d

文献信息

• FR2318627
  申请人：——

  公开号：——

  公开（公告）日：——
• US4207341A
  申请人：——

  公开号：US4207341A

  公开（公告）日：1980-06-10
• US4278680A
  申请人：——

  公开号：US4278680A

  公开（公告）日：1981-07-14
• Preparation of phenylethylbenzamide derivatives as modulators of DNMT3 activity
  作者：Anzhelika Kabro、Hugo Lachance、Iris Marcoux-Archambault、Valérie Perrier、Vicky Doré、Christina Gros、Véronique Masson、Jean-Marc Gregoire、Frédéric Ausseil、David Cheishvili、Nathalie Bibens Laulan、Yves St-Pierre、Moshe Szyf、Paola B. Arimondo、Alexandre Gagnon

  DOI：10.1039/c3md00214d

  日期：——

  DNA-methyltransferases (DNMTs) are a class of epigenetic enzymes that catalyze the transfer of a methyl moiety from the methyl donor S-adenosyl-L-methionine onto the C5 position of cytosine in DNA. This process is dysregulated in cancers and leads to the hypermethylation and silencing of tumor suppressor genes. The development of potent and selective inhibitors of DNMTs is of utmost importance for the discovery of new therapies for the treatment of cancer. We report herein the synthesis and DNMT inhibitory activity of 29 analogues derived from NSC 319745. The effect of selected compounds on the methylation level in the MDA-MB-231 human breast cancer cell line was evaluated using a luminometric methylation assay. Molecular docking studies have been conducted to propose a binding mode for this series.

  DNA甲基转移酶（DNMTs）是一类表观遗传酶，能催化将甲基供体S-腺苷-L-甲硫氨酸上的甲基基团转移到DNA中胞嘧啶的C5位置上。这一过程在癌症中发生失调，导致肿瘤抑制基因的高甲基化和沉默。开发强效且特异的DNMT抑制剂对于发现新的癌症治疗方法至关重要。本文报告了29种源自NSC 319745的类似物的合成及其DNMT抑制活性。使用发光甲基化测定法评估了选定化合物在人乳腺癌细胞系MDA-MB-231中对甲基化水平的影响。进行了分子对接研究，以提出该系列化合物的结合模式。
• Hypoglycaemically and hypolipidaemically active derivatives of
  申请人：Boehringer-Mannheim GmbH

  公开号：US04207341A1

  公开（公告）日：1980-06-10

  Phenylacetic acid derivatives of the formula ##STR1## wherein A is an aryl radical optionally substituted by halogen, trifluoromethyl, alkyl, alkoxy, alkenyloxy, alkoxyalkoxy, alkyl-substituted amino or aryloxy, or a heterocyclic ring system optionally substituted by halogen, alkyl or alkoxy, Y is a valency bond or an optionally branched alkylene radical containing up to 3 carbon atoms, and R.sub.1 and R.sub.2 each independently is hydrogen or a lower alkyl radical, or a physiologically compatible salt or ester thereof, exhibit marked hypoglycaemic and hypolipidaemic activity.

  Phenylacetic acid derivatives of the formula ##STR1## wherein A is an aryl radical optionally substituted by halogen, trifluoromethyl, alkyl, alkoxy, alkenyloxy, alkoxyalkoxy, alkyl-substituted amino or aryloxy, or a heterocyclic ring system optionally substituted by halogen, alkyl or alkoxy, Y is a valency bond or an optionally branched alkylene radical containing up to 3 carbon atoms, and R.sub.1 and R.sub.2 each independently is hydrogen or a lower alkyl radical, or a physiologically compatible salt or ester thereof, exhibit marked hypoglycaemic and hypolipidaemic activity.