(3S)-N-(5-nitropyrimidin-2-yl)pyrrolidin-3-ol | 939376-81-5

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (3S)-N-(5-nitropyrimidin-2-yl)pyrrolidin-3-ol
• 英文别名: (S)-N-(5-nitro-pyrimidin-2-yl)-pyrrolidin-3-ol；(S)-N-(5-nitropyrimidin-2-yl)-pyrrolidin-3-ol；(3S)-1-(5-nitropyrimidin-2-yl)pyrrolidin-3-ol
• CAS: 939376-81-5
• 化学式: C₈H₁₀N₄O₃
• 分子量: 210.192
• InChiKey: JOOOLLCGSMDHKJ-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  95.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3S)-N-(5-nitropyrimidin-2-yl)pyrrolidin-3-ol 在 5% Pd(II)/C(eggshell) 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (S)-N-(5-aminopyrimidin-2-yl)-pyrrolidin-3-ol
  参考文献：
  名称：

  Discovery of Orally Active Carboxylic Acid Derivatives of 2-Phenyl-5-trifluoromethyloxazole-4-carboxamide as Potent Diacylglycerol Acyltransferase-1 Inhibitors for the Potential Treatment of Obesity and Diabetes

  摘要：

  Diacylglycerol acyltransferase-1 (DGAT-1) is the enzyme that catalyzes the final and committed step of triglyceride formation, namely, the acylation of diacylglycerol with acyl coenzyme A. DGAT-1 deficient mice demonstrate resistance to weight gain on high fat diet, improved insulin sensitivity, and reduced liver triglyceride content. Inhibition of DGAT-1 thus represents a potential novel approach for the treatment of obesity, dyslipidemia, and metabolic syndrome. In this communication, we report the identification of the lead structure 6 and our lead optimization efforts culminating in the discovery of potent, selective, and orally efficacious carboxylic acid derivatives of 2-phenyl-5-trifluoromethyloxazole-4-carboxarnides. In particular, compound 29 (DGAT-1 enzyme assay, IC(50) = 57 nM; CHO-K1 cell triglyceride formation assay, EC(50) = 0.5 mu M) demonstrated dose dependent inhibition of weight gain in diet induced obese (DIO) rats (0.3, 1, and 3 mg/kg, PO, qd) during a 21-day efficacy study. Furthermore, compound 29 demonstrated improved glucose tolerance determined by an oral glucose tolerance test (OGTT).

  DOI：

  10.1021/jm101580m
• 作为产物：
  描述：

  2-氯-5-硝基嘧啶 、 (S)-3-吡咯烷醇 以to give (S)—N-(5-nitropyrimidin-2-yl)-pyrrolidin-3-ol的产率得到(3S)-N-(5-nitropyrimidin-2-yl)pyrrolidin-3-ol
  参考文献：
  名称：

  Diacylglycerol acyltransferase inhibitors

  摘要：

  本文提供的是式(I)的化合物及其药学上可接受的盐，其中取代基如规范中所披露。这些化合物及其含有它们的药物组合物可用于治疗疾病，例如肥胖症、2型糖尿病和代谢综合征。

  公开号：

  US20070123504A1

文献信息

• DIACYLGLYCEROL ACYLTRANSFERASE INHIBITORS
  申请人：Bolin David Robert

  公开号：US20100190979A1

  公开（公告）日：2010-07-29

  Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of diseases such as, for example, obesity, type II diabetes mellitus and metabolic syndrome.

  本文提供了以下式(I)的化合物及其药学上可接受的盐，其中取代基如规范中所述。这些化合物及含有它们的药物组成物，可用于治疗疾病，例如肥胖症、2型糖尿病和代谢综合征。
• Diacylglycerol Acyltransferase Inhibitors
  申请人：Bolin David Robert

  公开号：US20100168419A1

  公开（公告）日：2010-07-01

  Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of diseases such as, for example, obesity, type II diabetes mellitus and metabolic syndrome.

  本文所提供的化合物具有公式（I）的结构，以及其药学上可接受的盐，其中取代基与规范中所披露的相同。这些化合物以及含有它们的制药组合物，可用于治疗疾病，例如肥胖症、2型糖尿病和代谢综合征。
• INHIBITORS OF DIACYLGLYCEROL ACYLTRANSFERASE (DGAT)
  申请人：F.HOFFMANN-LA ROCHE AG

  公开号：EP1963313A2

  公开（公告）日：2008-09-03
• US7714126B2
  申请人：——

  公开号：US7714126B2

  公开（公告）日：2010-05-11
• [EN] INHIBITORS OF DIACYGLYCEROL ACYLTRANSFERASE (DGAT)<br/>[FR] INHIBITEURS DE DIACYLGLYCÉROL ACYLTRANSFÉRASE (DGAT)
  申请人：HOFFMANN LA ROCHE

  公开号：WO2007060140A2

  公开（公告）日：2007-05-31

  [EN] Provided herein are compounds of the formula (I), as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of diseases such as, for example, obesity, type II diabetes mellitus and metabolic syndrome.
  [FR] La présente invention concerne des composés de formule (I), ainsi que des sels de qualité pharmaceutique desdits composés, dont les substituants sont ceux définis dans la description. Ces composés, ainsi que les préparations pharmaceutiques qui les contiennent, peuvent être employés dans le traitement de maladies telles que, par exemple, l'obésité, le diabète sucré de type II et le syndrome métabolique.