3-[2-(4-methoxy-phenyl)-2-(4-nitro-imidazol-1-yl)-propionyl]-4-methyl-5-phenyl-oxazolidin-2-one | 220907-93-7

• 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: 3-[2-(4-methoxy-phenyl)-2-(4-nitro-imidazol-1-yl)-propionyl]-4-methyl-5-phenyl-oxazolidin-2-one
• CAS: 220907-93-7
• 化学式: C₂₃H₂₂N₄O₆
• 分子量: 450.451
• InChiKey: KQFBEOXSHCCZGI-ZFUCPZCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  116.8
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3-[2-(4-methoxy-phenyl)-2-(4-nitro-imidazol-1-yl)-propionyl]-4-methyl-5-phenyl-oxazolidin-2-one 在 lithium hydroxide 、 草酰氯 作用下， 生成 2-(4-methoxy-phenyl)-2-(4-nitro-imidazol-1-yl)-1-pyrrolidin-1-yl-propan-1-one
  参考文献：
  名称：

  Synthesis and biological evaluation of an orally active ghrelin agonist that stimulates food consumption and adiposity in rats

  摘要：

  2-(2-Amino-2-methyl-propionylamino)-5-phenyl-pentanoic acid {1-[1-(4-methoxy-phenyl)-1-methyl-2-oxo-2-pyrrolidin-1-yl-ethyll-lH-imidazol-4-yl}-amide (LY444711, 6) is an orally active ghrelin agonist that binds with high affinity to and is a potent activator of the growth hormone secretagogue receptor la (GHS-R1a) receptor. In rat models of feeding behavior and pharmacology, 6 creates a positive energy balance and induces adiposity by stimulating food consumption and sparing fat utilization. As an orally active ghrelin agonist, 6 represents a new pharmacological tool to investigate the orexigenic role of ghrelin in regulating energy homeostasis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.09.027
• 作为产物：
  描述：

  对甲氧基苯乙酸乙酯 在 lithium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 草酰氯 、 偶氮二异丁腈 、 sodium hexamethyldisilazane 、 potassium carbonate 作用下， 生成 3-[2-(4-methoxy-phenyl)-2-(4-nitro-imidazol-1-yl)-propionyl]-4-methyl-5-phenyl-oxazolidin-2-one
  参考文献：
  名称：

  Synthesis and biological evaluation of an orally active ghrelin agonist that stimulates food consumption and adiposity in rats

  摘要：

  2-(2-Amino-2-methyl-propionylamino)-5-phenyl-pentanoic acid {1-[1-(4-methoxy-phenyl)-1-methyl-2-oxo-2-pyrrolidin-1-yl-ethyll-lH-imidazol-4-yl}-amide (LY444711, 6) is an orally active ghrelin agonist that binds with high affinity to and is a potent activator of the growth hormone secretagogue receptor la (GHS-R1a) receptor. In rat models of feeding behavior and pharmacology, 6 creates a positive energy balance and induces adiposity by stimulating food consumption and sparing fat utilization. As an orally active ghrelin agonist, 6 represents a new pharmacological tool to investigate the orexigenic role of ghrelin in regulating energy homeostasis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.09.027

文献信息

• Method for treating emesis with ghrelin agonists
  申请人：Heiman Louis Mark

  公开号：US20050277677A1

  公开（公告）日：2005-12-15

  The present invention relates to a method comprising administering to a patient diagnosed as being in need of treatment for nausea, emesis, or symptoms associated therewith comprising administering to a patient in need thereof a compound of formula (I) wherein: R 1 is C 6 H 5 CH 2 OCH 2 —, C 6 H 5 (CH 2 ) 3 — or indol-3-ylmethyl; Y is pyrrolidinyl, 4-methyl-piperidinyl or NR 2 R 2 ; R 2 are each independently C 1 -C 6 alkyl; R 3 is 2-napthyl or phenyl para-substituted by W; W is H, F, CF 3 , C 1 -C 6 alkoxy or phenyl; and R 4 is H or CH 3 ; or a pharmaceutically acceptable salt or solvate thereof, in an amount that is effective in treating nausea, emesis, or symptoms associated therewith in said patient.

  本发明涉及一种方法，包括向被诊断为需要治疗恶心、呕吐或相关症状的患者施用化合物(I)的方法，其中：R1是C6H5CH2OCH2—、C6H5(CH2)3—或indol-3-ylmethyl;Y是吡咯烷基、4-甲基哌啶基或NR2R2;R2各自独立地是C1-C6烷基;R3是2-萘基或苯基对位取代W;W是H、F、CF3、C1-C6烷氧基或苯基; R4是H或CH3;或其药学上可接受的盐或溶剂，用于治疗该患者的恶心、呕吐或相关症状。
• Synthesis and biological evaluation of an orally active ghrelin agonist that stimulates food consumption and adiposity in rats
  作者：Charles W. Lugar、Michael P. Clay、Terry D. Lindstrom、Andrea L. Woodson、David Smiley、Mark L. Heiman、Jeffrey A. Dodge

  DOI：10.1016/j.bmcl.2004.09.027

  日期：2004.12

  2-(2-Amino-2-methyl-propionylamino)-5-phenyl-pentanoic acid 1-[1-(4-methoxy-phenyl)-1-methyl-2-oxo-2-pyrrolidin-1-yl-ethyll-lH-imidazol-4-yl}-amide (LY444711, 6) is an orally active ghrelin agonist that binds with high affinity to and is a potent activator of the growth hormone secretagogue receptor la (GHS-R1a) receptor. In rat models of feeding behavior and pharmacology, 6 creates a positive energy balance and induces adiposity by stimulating food consumption and sparing fat utilization. As an orally active ghrelin agonist, 6 represents a new pharmacological tool to investigate the orexigenic role of ghrelin in regulating energy homeostasis. (C) 2004 Elsevier Ltd. All rights reserved.