Methyl 2-(3-oxocyclopentyl)-2-pyridin-2-ylsulfonylacetate | 865706-16-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: Methyl 2-(3-oxocyclopentyl)-2-pyridin-2-ylsulfonylacetate
• CAS: 865706-16-7
• 化学式: C₁₃H₁₅NO₅S
• 分子量: 297.332
• InChiKey: IMEIUDFADVAGKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  98.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl 2-(3-oxocyclopentyl)-2-pyridin-2-ylsulfonylacetate 在 sodium hydride 、 N-氟代双苯磺酰胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 、
  参考文献：
  名称：

  Discovery of tetrahydro-cyclopenta[b]indole as selective LXRs modulator

  摘要：

  A series of tetrahydro-cyclopenta[b] indoles modulating the activity of the liver-X-receptor (LXR) were derived from a high throughput screening hit. The potency and selectivity for LXR beta versus LXR alpha was improved. One compound, administered to wild-type mice modestly increased plasma HDL-cholesterol with no change in plasma triglycerides (TG) and reduced effects on liver TG content compared to T0901317. This novel series of LXR agonists shows promise to improve therapeutic efficacy with reduced potential to increase TG. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.01.109
• 作为产物：
  描述：

  2-环戊烯酮 、 (pyridine-2-sulfonyl)-acetic acid methyl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 Methyl 2-(3-oxocyclopentyl)-2-pyridin-2-ylsulfonylacetate
  参考文献：
  名称：

  Discovery of tetrahydro-cyclopenta[b]indole as selective LXRs modulator

  摘要：

  A series of tetrahydro-cyclopenta[b] indoles modulating the activity of the liver-X-receptor (LXR) were derived from a high throughput screening hit. The potency and selectivity for LXR beta versus LXR alpha was improved. One compound, administered to wild-type mice modestly increased plasma HDL-cholesterol with no change in plasma triglycerides (TG) and reduced effects on liver TG content compared to T0901317. This novel series of LXR agonists shows promise to improve therapeutic efficacy with reduced potential to increase TG. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.01.109

文献信息

• [EN] TETRAHYDROCARBAZOLES AND DERIVATIVES<br/>[FR] TETRAHYDROCARBAZOLES ET DERIVES
  申请人：HOFFMANN LA ROCHE

  公开号：WO2005092856A1

  公开（公告）日：2005-10-06

  The present invention relates to compounds of the formula (I) wherein R1, R2, R3, R4, R5, X1, X2, X3, X4, n, and k are defined in the description and claims, and pharmaceutically acceptable salts and/or pharmaceutically acceptable esters thereof. The compounds are useful for in the treatment and prophylaxis of diseases which are modulated by LXRα and/or LXRß agonists, including increased lipid and cholesterol levels, particularly low HDL-cholesterol, high LDL-cholesterol, atherosclerotic diseases, diabetes, particularly non-insulin dependent diabetes mellitus, metabolic syndrome, dyslipidemia, Alzheimer's disease, sepsis, inflammatory diseases such as colitis, pancreatitis, cholestasis/fibrosis of the liver, and diseases that have an inflammatory component such as Alzheimer's disease or impaired/improvable cognitive function.

  本发明涉及式(I)的化合物，其中R1、R2、R3、R4、R5、X1、X2、X3、X4、n和k在描述和权利要求中有定义，并且其药学上可接受的盐和/或药学上可接受的酯。这些化合物对于治疗和预防由LXRα和/或LXRß激动剂调节的疾病是有用的，包括增加的脂质和胆固醇水平，特别是低HDL-胆固醇、高LDL-胆固醇、动脉粥样硬化疾病、糖尿病，特别是非胰岛素依赖型糖尿病，代谢综合征，血脂异常，阿尔茨海默病，败血症，炎症性疾病如结肠炎、胰腺炎、肝胆瘀积/肝纤维化，以及具有炎症成分的疾病，如阿尔茨海默病或认知功能受损/可改善的疾病。
• Tetrahydrocarbazoles and derivatives
  申请人：Dehmlow Henrietta

  公开号：US20050215577A1

  公开（公告）日：2005-09-29

  The present invention relates to compounds of the formula (I) wherein R 1 , R 2 , R 3 , R 4 , R 5 , X 1 , X 2 , X 3 , X 4 , n, and k are defined in the description and claims, and pharmaceutically acceptable salts and/or pharmaceutically acceptable esters thereof. The compounds are useful for in the treatment and prophylaxis of diseases which are modulated by LXRα and/or LXRβ agonists, including increased lipid and cholesterol levels, particularly low HDL-cholesterol, high LDL-cholesterol, atherosclerotic diseases, diabetes, particularly non-insulin dependent diabetes mellitus, metabolic syndrome, dyslipidemia, Alzheimer's disease, sepsis, inflammatory diseases such as colitis, pancreatitis, cholestasis/fibrosis of the liver, and diseases that have an inflammatory component such as Alzheimer's disease or impaired/improvable cognitive function.

  本发明涉及式(I)的化合物，其中R1、R2、R3、R4、R5、X1、X2、X3、X4、n和k在说明书和权利要求中有定义，并且其药学上可接受的盐和/或药学上可接受的酯。这些化合物在LXRα和/或LXRβ激动剂调节的疾病的治疗和预防中有用，包括增加的脂质和胆固醇水平，特别是低HDL-胆固醇，高LDL-胆固醇，动脉粥样硬化疾病，糖尿病，特别是非胰岛素依赖性糖尿病，代谢综合征，脂质代谢异常，阿尔茨海默病，败血症，炎症性疾病，如结肠炎，胰腺炎，肝胆瘤/纤维化和具有炎症成分的疾病，如阿尔茨海默病或受损/可改善的认知功能。
• TETRAHYDROCARBAZOLES AND DERIVATIVES
  申请人：Dehmlow Henrietta

  公开号：US20100216833A1

  公开（公告）日：2010-08-26

  The present invention relates to compounds of the formula (I) wherein R 1 , R 2 , R 3 , R 4 , R 5 , X 1 , X 2 , X 3 , X 4 , n, and k are defined in the description and claims, and pharmaceutically acceptable salts and/or pharmaceutically acceptable esters thereof. The compounds are useful for in the treatment and prophylaxis of diseases which are modulated by LXRα and/or LXRβ agonists, including increased lipid and cholesterol levels, particularly low HDL-cholesterol, high LDL-cholesterol, atherosclerotic diseases, diabetes, particularly non-insulin dependent diabetes mellitus, metabolic syndrome, dyslipidemia, Alzheimer's disease, sepsis, inflammatory diseases such as colitis, pancreatitis, cholestasis/fibrosis of the liver, and diseases that have an inflammatory component such as Alzheimer's disease or impaired/improvable cognitive function.

  本发明涉及式（I）的化合物，其中R1、R2、R3、R4、R5、X1、X2、X3、X4、n和k在说明书和权利要求书中定义，并且其药学上可接受的盐和/或药学上可接受的酯。该化合物用于治疗和预防LXRα和/或LXRβ激动剂调节的疾病，包括增加的脂质和胆固醇水平，特别是低HDL胆固醇，高LDL胆固醇，动脉粥样硬化疾病，糖尿病，特别是非胰岛素依赖性糖尿病，代谢综合征，血脂异常，阿尔茨海默病，败血症，炎症性疾病，如结肠炎，胰腺炎，肝胆瘤/纤维化以及有炎症成分的疾病，例如阿尔茨海默病或受损/可改善的认知功能。
• US7906546B2
  申请人：——

  公开号：US7906546B2

  公开（公告）日：2011-03-15
• Discovery of tetrahydro-cyclopenta[b]indole as selective LXRs modulator
  作者：Hassen Ratni、Denise Blum-Kaelin、Henrietta Dehmlow、Peter Hartman、Philippe Jablonski、Raffaello Masciadri、Cyrille Maugeais、Angelique Patiny-Adam、Narendra Panday、Matthew Wright

  DOI：10.1016/j.bmcl.2009.01.109

  日期：2009.3

  A series of tetrahydro-cyclopenta[b] indoles modulating the activity of the liver-X-receptor (LXR) were derived from a high throughput screening hit. The potency and selectivity for LXR beta versus LXR alpha was improved. One compound, administered to wild-type mice modestly increased plasma HDL-cholesterol with no change in plasma triglycerides (TG) and reduced effects on liver TG content compared to T0901317. This novel series of LXR agonists shows promise to improve therapeutic efficacy with reduced potential to increase TG. (C) 2009 Elsevier Ltd. All rights reserved.