5-氯-N-[2-(4-乙基苯基)乙基]-2-甲氧基苯甲酰胺 | 64353-17-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-氯-N-[2-(4-乙基苯基)乙基]-2-甲氧基苯甲酰胺
• 英文名称: 5-chloro-2-methoxy-N-<2-(p-ethylphenyl)ethyl>benzamide
• 英文别名: 5-chloro-2-methoxy-N-(2-<4-ethylphenyl>-ethyl)-benzamide；5-Chloro-N-[2-(4-ethylphenyl)ethyl]-2-methoxybenzamide
• CAS: 64353-17-9
• 化学式: C₁₈H₂₀ClNO₂
• 分子量: 317.815
• InChiKey: JNXFPQLNOWRITE-UHFFFAOYSA-N

物化性质

• 沸点：
  462.4±45.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-(2-<5-chloro-2-methoxy-benzamido>-ethyl)-acetophenone 在 palladium on activated charcoal sodium tetrahydroborate 、 氢气 、 碘 作用下， 以 乙醇 、 xylene 为溶剂， 反应 9.17h， 生成 5-氯-N-[2-(4-乙基苯基)乙基]-2-甲氧基苯甲酰胺
  参考文献：
  名称：

  Receptor binding sites of hypoglycemic sulfonylureas and related [(acylamino)alkyl]benzoic acids

  摘要：

  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.

  DOI：

  10.1021/jm00367a016

文献信息

• 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。
• Acylamino(alkyl)benzene derivatives and process for preparing them
  申请人：Hoechst Aktiengesellschaft

  公开号：US04158063A1

  公开（公告）日：1979-06-12

  The invention relates to acylamino(alkyl)benzene derivatives of the general formula ##STR1## in which W represents a group which can be converted into a carboxyl group, or an aldehyde group or an oxymethyl group or their derivatives or also a low molecular weight alkyl group, preferably a methyl group, X represents an aromatic or hetero-aromatic ring system, Y represents a single chemical bond or a hydrocarbon bridge, and Z represents hydrogen or one or even several other substituents, To their preparation and to pharmaceutical compositions containing them. The compounds have blood sugar lowering activity and may be used in the therapy of diabetes mellitus.

  该发明涉及通式为##STR1##的酰胺基（烷基）苯衍生物，其中W表示可转化为羧基、醛基或氧甲基基团或它们的衍生物或低分子量烷基，优选为甲基基团，X表示芳香或杂芳环系，Y表示单一化学键或烃桥，Z表示氢或一个或多个其他取代基，以及它们的制备方法和含有它们的制药组合物。这些化合物具有降低血糖活性，并可用于糖尿病治疗中。
• [EN] SULFONYLUREAS AND RELATED COMPOUNDS AND USE OF SAME<br/>[FR] SULFONYLURÉES, COMPOSÉS APPARENTÉS, ET LEUR UTILISATION
  申请人：UNIV QUEENSLAND

  公开号：WO2016131098A1

  公开（公告）日：2016-08-25

  ABSTRACT The present invention provides for certain sulfonyl ureas and related compounds which have advantageous properties and show useful activity in the inhibition of activation of the NLRP3 inflammasome. Such compounds are useful in the treatment of a wide range of disorders in which the inflammation process, or more specifically the NLRP3 inflammasome, have been implicated as being a key factor.
• 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.