3,4-Dihydro-6-nitro-2H-1,4-benzoxazin-2-carbonsaeuremethylester | 84831-34-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 3,4-Dihydro-6-nitro-2H-1,4-benzoxazin-2-carbonsaeuremethylester
• 英文别名: methyl 6-nitro-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate
• CAS: 84831-34-5
• 化学式: C₁₀H₁₀N₂O₅
• 分子量: 238.2
• InChiKey: XHOQDXSUAQJULB-UHFFFAOYSA-N

物化性质

• 熔点：
  166-167 °C(Solv: benzene (71-43-2))
• 沸点：
  388.6±42.0 °C(Predicted)
• 密度：
  1.378±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  93.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,4-Dihydro-6-nitro-2H-1,4-benzoxazin-2-carbonsaeuremethylester 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 (R)-(6-Nitro-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-yl)methanol
  参考文献：
  名称：

  Potent, Selective, and Orally Efficacious Antagonists of Melanin-Concentrating Hormone Receptor 1

  摘要：

  The high expression of MCH in the hypothalamus with the lean hypophagic phenotype coupled with increased resting metabolic rate and resistance to high fat diet-induced obesity of MCH KO mice has spurred considerable efforts to develop small molecule MCHR1 antagonists. Starting from a lead thienopyrimidinone series, structure-activity studies at the 3- and 6-positions of the thienopyrimidinone core afforded potent and selective MCHR1 antagonists with representative examples having suitable pharmacokinetic properties. Based on structure-activity relationships, a structural model for MCHR1 was constructed to explain the binding mode of these antagonists. In general, a good correlation was observed between pK(a)s and activity in the right-hand side of the template, with Asp123 playing an important role in the enhancement of binding affinity. A representative example when evaluated chronically in diet-induced obese mice resulted in good weight loss effects. These antagonists provide a viable lead series in the discovery of new therapies for the treatment of obesity.

  DOI：

  10.1021/jm060572f
• 作为产物：
  描述：

  2,3-二溴丙酸甲酯 、 2-氨基-4-硝基苯酚 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以66%的产率得到3,4-Dihydro-6-nitro-2H-1,4-benzoxazin-2-carbonsaeuremethylester
  参考文献：
  名称：

  Bartsch, Herbert; Schwarz, Otto, Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 1189 - 1193

  摘要：

  DOI：

文献信息

• BARTSCH, H.;SCHWARZ, O., J. HETEROCYCL. CHEM., 1982, 19, N 5, 1189-1193
  作者：BARTSCH, H.、SCHWARZ, O.

  DOI：——

  日期：——
• Potent, Selective, and Orally Efficacious Antagonists of Melanin-Concentrating Hormone Receptor 1
  作者：Francis X. Tavares、Kamal A. Al-Barazanji、Eric C. Bigham、Michael J. Bishop、Christy S. Britt、David L. Carlton、Paul L. Feldman、Aaron S. Goetz、Mary K. Grizzle、Yu C. Guo、Anthony L. Handlon、Donald L. Hertzog、Diane M. Ignar、Daniel G. Lang、Ronda J. Ott、Andrew J. Peat、Hui-Qiang Zhou

  DOI：10.1021/jm060572f

  日期：2006.11.30

  The high expression of MCH in the hypothalamus with the lean hypophagic phenotype coupled with increased resting metabolic rate and resistance to high fat diet-induced obesity of MCH KO mice has spurred considerable efforts to develop small molecule MCHR1 antagonists. Starting from a lead thienopyrimidinone series, structure-activity studies at the 3- and 6-positions of the thienopyrimidinone core afforded potent and selective MCHR1 antagonists with representative examples having suitable pharmacokinetic properties. Based on structure-activity relationships, a structural model for MCHR1 was constructed to explain the binding mode of these antagonists. In general, a good correlation was observed between pK(a)s and activity in the right-hand side of the template, with Asp123 playing an important role in the enhancement of binding affinity. A representative example when evaluated chronically in diet-induced obese mice resulted in good weight loss effects. These antagonists provide a viable lead series in the discovery of new therapies for the treatment of obesity.
• Bartsch, Herbert; Schwarz, Otto, Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 1189 - 1193
  作者：Bartsch, Herbert、Schwarz, Otto

  DOI：——

  日期：——