5-chloro-N-[2-(4-hydroxyphenyl)ethyl]-2-methoxybenzamide | 41859-64-7

• 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: 5-chloro-N-[2-(4-hydroxyphenyl)ethyl]-2-methoxybenzamide
• 英文别名: 5-chloro-N-(4-hydroxyphenylethyl)-2-methoxybenzamide
• CAS: 41859-64-7
• 化学式: C₁₆H₁₆ClNO₃
• 分子量: 305.761
• InChiKey: MQNJDHXODGUTNV-UHFFFAOYSA-N

物化性质

• 沸点：
  495.2±45.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-chloro-N-[2-(4-hydroxyphenyl)ethyl]-2-methoxybenzamide 在 水 、 potassium carbonate 、 lithium hydroxide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 2-[4-[2-[(5-Chloro-2-methoxybenzoyl)amino]ethyl]phenoxy]acetic 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
• 作为产物：
  描述：

  对羟基苯乙胺 、 5-氯-2-甲氧基苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以57%的产率得到5-chloro-N-[2-(4-hydroxyphenyl)ethyl]-2-methoxybenzamide
  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

• Ligand-coupled initiator polymers and methods of use
  申请人：SurModics, Inc.

  公开号：US20040203075A1

  公开（公告）日：2004-10-14

  Initiator polymers having an initiator group and a ligand group are provided. The initiator polymers are capable of specifically binding to a receptor on a surface. Using a macromer system, the initiator polymers are useful for the formation of a polymeric matrix on the surface of a material. In particular, initiator polymers are provided that have specificity to pancreatic &bgr; cells and can be used to encapsulate cells for transplantation and the treatment of diabetes.

  本发明提供了具有引发基团和配体基团的引发聚合物。这些引发聚合物能够特异性地结合到表面上的受体上。利用一种大分子体系，这些引发聚合物可用于在材料表面形成聚合物基质。特别地，本发明提供了具有对胰岛素β细胞特异性的引发聚合物，可用于包埋细胞进行移植和治疗糖尿病。
• LIGAND-COUPLED INITIATOR POLYMERS AND METHODS OF USE
  申请人：Chudzik Stephen J.

  公开号：US20110040057A1

  公开（公告）日：2011-02-17

  Initiator polymers having an initiator group and a ligand group are provided. The initiator polymers are capable of specifically binding to a receptor on a surface. Using a macromer system, the initiator polymers are useful for the formation of a polymeric matrix on the surface of a material. In particular, initiator polymers are provided that have specificity to pancreatic β cells and can be used to encapsulate cells for transplantation and the treatment of diabetes.

  本发明提供了具有引发基团和配体基团的引发聚合物。该引发聚合物能够特异性地结合到表面上的受体。使用大分子体系，该引发聚合物可用于在材料表面形成聚合物基质。特别地，本发明提供了具有对胰岛素β细胞特异性的引发聚合物，可用于包埋细胞进行移植和治疗糖尿病。
• Receptor binding sites of hypoglycemic sulfonylureas and related [(acylamino)alkyl]benzoic acids
  作者：George R. Brown、Alan J. Foubister

  DOI：10.1021/jm00367a016

  日期：1984.1

  The blood glucose level lowering activity of [(acylamino)ethyl]benzoic acids, such as p-[2-(5-chloro-2-methoxy-benzamido)ethyl]benzoic acid (HB699, 2), is discussed in terms of binding at putative insulin-releasing receptor sites of pancreatic beta cells. The hypoglycemic potencies found for synthetic analogues of 2 indicate that high hypoglycemic activity is only found when a carboxyl group or a group that is readily oxidized to carboxyl in vivo, such as methyl, is attached to the aromatic ring of the phenethyl group. It is proposed that this carboxyl group is able to bind at the same receptor site as the SO2NHCONH group of the sulfonylurea drugs, such as tolbutamide (3). The role of the benzamide group in 2 was attributed to protein binding.
• Inhibition of ATP-sensitive K+-channels by a sulfonylurea analogue with a phosphate group
  作者：Katja Hastedt、Uwe Panten

  DOI：10.1016/s0006-2952(02)01566-6

  日期：2003.2

  Hypoglycaemic sulfortylureas initiate insulin secretion by direct inhibition of ATP-sensitive K--channels in the pancreatic beta-cells. These channels are composed of two proteins, a pore-forming subunit (K(IR)6.2 in the case of beta-cells) and a regulatory subunit, the sulfonylurea receptor (SUR). In the present study we characterised the interaction with SURs of the new sulfonylurea analogues 5-chloro-N-[2-(4-hydroxyphenyl)ethyl]-2-methoxvbenzamide (compound I) and 4-[2-(5-chloro-2-methoxybenzamido)ethyl]phenyl}phosphate (compound I). Compounds I and II differ from the sulfonylurea analogue meglitinide only in so far as the carboxylic group of meglitinide is replaced by a hydroxyl group or a phosphate group. respectively. The binding affinities of compound II for the SUR subtypes SUR1 (identified in beta-cells) and SUR2A (identified in heart and skeletal muscle) were higher by 55 or 21-fold, respectively, than the corresponding affinities for compound I. In inside-out patch-clamp experiments compound II inhibited ATP-sensitive K-channels of the SUR1/K(IR)6.2-type (characteristic of beta-cells) with an IC50 value of 0.16 muM which is 6-fold lower than the corresponding value for meglitinide. These findings strongly support the conclusion that the interaction of sulfortylureas and acidic analogues with SURs is favoured by the anionic group of these drugs and that a phosphate group allows more efficient ligand interaction with SUR1 than a carboxylic group. (C) 2002 Elsevier Science Inc. All rights reserved.
• EP1613749A2
  申请人：——

  公开号：EP1613749A2

  公开（公告）日：2006-01-11