4-(2-<5-chloro-2-methoxy-benzamido>-ethyl)-acetophenone | 60531-37-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(2-<5-chloro-2-methoxy-benzamido>-ethyl)-acetophenone
• 英文别名: 4-[2-(5-chloro-2-methoxybenzamido)-ethyl]-acetophenone；4-<2-(5-Chlor-2-methoxybenzamido)-ethyl>-acetophenon；4-[2-(5-Chlor-2-methoxybenzamido)-ethyl]-acetophenon；N-[2-(4-acetylphenyl)ethyl]-5-chloro-2-methoxybenzamide
• CAS: 60531-37-5
• 化学式: C₁₈H₁₈ClNO₃
• 分子量: 331.799
• InChiKey: QACIPNCRDPCEES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  5-氯-2-甲氧基-N-(2-苯基乙基)苯甲酰胺	5-chloro-2-methoxy-N-phenethylbenzamide	33924-49-1	C16H16ClNO2	289.762

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  5-氯-N-[2-(4-乙基苯基)乙基]-2-甲氧基苯甲酰胺	5-chloro-2-methoxy-N-<2-(p-ethylphenyl)ethyl>benzamide	64353-17-9	C18H20ClNO2	317.815
  美各里替尼	meglitinide	54870-28-9	C17H16ClNO4	333.771
  ——	4-[2-(5-chloro-2-methoxybenzamido)-ethyl]-phenylglyoxylic acid	62910-77-4	C18H16ClNO5	361.782
  ——	4-[2-(5-chloro-2-methoxybenzamido)-ethyl]-phenylacetic acid	62910-22-9	C18H18ClNO4	347.798
  ——	3-{4-[2-(5-chloro-2-methoxybenzamido)-ethyl]-phenyl}-butyric acid	61629-87-6	C20H22ClNO4	375.852
  ——	4-[2-(2-methoxybenzamido)-ethyl]-phenylacetic acid	62910-37-6	C18H19NO4	313.353

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  5-氯-2-甲氧基-N-(2-苯基乙基)苯甲酰胺 、 乙酰氯 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 生成 4-(2-<5-chloro-2-methoxy-benzamido>-ethyl)-acetophenone
  参考文献：
  名称：

  FR2296407

  摘要：

  公开号：

文献信息

• 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.
• Benzoic acids, their derivatives and process for preparing them
  申请人：Hoechst Aktiengesellschaft

  公开号：US04221815A1

  公开（公告）日：1980-09-09

  Acyl-aminoalkyl-benzoic acid and derivates thereof show a blood sugar lowering effect upon oral administration and can be used as orally applicable hypoglycemiants.

  酰基-氨基烷基苯甲酸及其衍生物经口服后显示降低血糖的效果，并可用作口服适用的降血糖药物。
• FR2318627
  申请人：——

  公开号：——

  公开（公告）日：——
• DE2517229
  申请人：——

  公开号：——

  公开（公告）日：——
• US4113871A
  申请人：——

  公开号：US4113871A

  公开（公告）日：1978-09-12