N-Benzyloxycarbonyl-glycinphenacyl-amid | 18807-52-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-Benzyloxycarbonyl-glycinphenacyl-amid
• 英文别名: benzyl N-[2-oxo-2-(phenacylamino)ethyl]carbamate
• CAS: 18807-52-8
• 化学式: C₁₈H₁₈N₂O₄
• 分子量: 326.352
• InChiKey: FNVVQSTXQVXGSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  84.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-Benzyloxycarbonyl-glycinphenacyl-amid 在 sodium tetrahydroborate 、 palladium 10% on activated carbon 、 ammonium acetate 、 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 7.0h， 生成 N-methyl-1-(4-phenyl-1H-imidazol-2-yl)methanamine
  参考文献：
  名称：

  Identification of a dual δ OR antagonist/μ OR agonist as a potential therapeutic for diarrhea-predominant Irritable Bowel Syndrome (IBS-d)

  摘要：

  A small set of acyclic analogs 5 were prepared to explore their structure-activity relationships (SARs) relative to heterocyclic core, opioid receptor (OR) agonists 4. Compound 5l was found to have very favorable OR binding affinities at the δ and μ ORs (r K(i) δ=1.3 nM; r K(i) μ=0.9 nM; h K(i) μ=1.7 nM), with less affinity for the κ OR (gp K(i) κ=55 nM). The OR functional profile for 5l varied from the previously described dual δ/μ OR agonists 4, with 5l being a potent, mixed dual δ OR antagonist/μ OR agonist [δ IC(50)=89 nM (HVD); μ EC(50)=1 nM (GPI); κ EC(50)=1.6 μM (GPC)]. Compound 5l has progressed through a clinical Phase II Proof of Concept study on 800 patients suffering from diarrhea-predominant Irritable Bowel Syndrome (IBS-d). This Phase II study was recently completed successfully, with 5l demonstrating statistically significant efficacy over placebo.

  DOI：

  10.1016/j.bmcl.2012.05.042
• 作为产物：
  描述：

  N-苄氧羰基甘氨酸-4-硝基苯酯 、 α-Aminoacetophenone hydrobromide 生成 N-Benzyloxycarbonyl-glycinphenacyl-amid
  参考文献：
  名称：

  合成δ-氨基松油酸类似物作为潜在的抗疟药

  摘要：

  作为潜在抗疟药合成研究的一部分，制备了许多δ-氨基乳油酸（5-氨基-4-氧戊酸）类似物：（1）5-（吗啉代-，哌啶子基-或N-（2）1-氨基-4-（苯基或对氯苯基）磺酰基丁烷-2-一盐酸盐，（3）1-（苯甲酰基或烟酰基-）2-甘氨酰氢溴酸盐， （4）1 -甘氨酰- 2-（p甲苯基-或p -氯苯基- ） -氢溴酸sulphonylhydrazine，（5）甘氨酸phenacyl-或p -bromophenacyl -酰胺氢溴酸盐，（6）甘氨酸2-（苯基-或p -甲苯基-）磺酰基乙基酰胺氢溴酸盐和（7）1-乙氧基羰基-2-甘氨酰肼盐酸盐。

  DOI：

  10.1039/j39680001399

文献信息

• Synthetic Studies toward Diazonamide A. A Novel Approach for Polyoxazole Synthesis
  作者：Peter Wipf、Joey-Lee Methot

  DOI：10.1021/ol0157196

  日期：2001.5.1

  [Reaction in text]The indole-bisoxazole fragment of diazonamide A was prepared by a Chan-type rearrangement of a tertiary amide. This approach represents a remarkably direct strategy for polyoxazole synthesis.

  [本文的反应]重氮酰胺的Chan型重排制备了重氮酰胺A的吲哚-双恶唑片段。该方法代表了聚恶唑合成的非常直接的策略。
• Identification of a dual δ OR antagonist/μ OR agonist as a potential therapeutic for diarrhea-predominant Irritable Bowel Syndrome (IBS-d)
  作者：Henry J. Breslin、Craig J. Diamond、Robert W. Kavash、Chaozhong Cai、Alexey B. Dyatkin、Tamara A. Miskowski、Sui-Po Zhang、Paul R. Wade、Pamela J. Hornby、Wei He

  DOI：10.1016/j.bmcl.2012.05.042

  日期：2012.7

  A small set of acyclic analogs 5 were prepared to explore their structure-activity relationships (SARs) relative to heterocyclic core, opioid receptor (OR) agonists 4. Compound 5l was found to have very favorable OR binding affinities at the δ and μ ORs (r K(i) δ=1.3 nM; r K(i) μ=0.9 nM; h K(i) μ=1.7 nM), with less affinity for the κ OR (gp K(i) κ=55 nM). The OR functional profile for 5l varied from the previously described dual δ/μ OR agonists 4, with 5l being a potent, mixed dual δ OR antagonist/μ OR agonist [δ IC(50)=89 nM (HVD); μ EC(50)=1 nM (GPI); κ EC(50)=1.6 μM (GPC)]. Compound 5l has progressed through a clinical Phase II Proof of Concept study on 800 patients suffering from diarrhea-predominant Irritable Bowel Syndrome (IBS-d). This Phase II study was recently completed successfully, with 5l demonstrating statistically significant efficacy over placebo.
• Synthesis of δ-aminolaevulinic acid analogues as potential antimalarial agents
  作者：O. L. Salerni、B. E. Smart、A. Post、C. C. Cheng

  DOI：10.1039/j39680001399

  日期：——

  As part of a study of the synthesis of potential antimalarial agents, a number of analogues of δ-aminolaevulinic (5-amino-4-oxopentanoic) acid were prepared: (1) methyl 5-(morpholino-, piperidino-, or N-methylbenzyl-amino-)4-oxopentanoate, (2) 1-amino-4-(phenyl- or p-chlorophenyl)sulphonylbutan-2-one hydrochloride, (3) 1-(benzoyl- or nicotinoyl-)2-glycylhydrazine hydrobromide, (4) 1-glycyl-2-(p-tolyl-

  作为潜在抗疟药合成研究的一部分，制备了许多δ-氨基乳油酸（5-氨基-4-氧戊酸）类似物：（1）5-（吗啉代-，哌啶子基-或N-（2）1-氨基-4-（苯基或对氯苯基）磺酰基丁烷-2-一盐酸盐，（3）1-（苯甲酰基或烟酰基-）2-甘氨酰氢溴酸盐， （4）1 -甘氨酰- 2-（p甲苯基-或p -氯苯基- ） -氢溴酸sulphonylhydrazine，（5）甘氨酸phenacyl-或p -bromophenacyl -酰胺氢溴酸盐，（6）甘氨酸2-（苯基-或p -甲苯基-）磺酰基乙基酰胺氢溴酸盐和（7）1-乙氧基羰基-2-甘氨酰肼盐酸盐。