(S)-2-(hydroxymethyl)-1-(pyridin-2-yl)pyrrolidine | 199117-77-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-2-(hydroxymethyl)-1-(pyridin-2-yl)pyrrolidine
• 英文别名: (S)-(1-(pyridin-2-yl)pyrrolidin-2-yl)methanol；(S)-N-(pyridin-2-yl)-2-(hydroxymethyl)pyrrolidine；N-(2-Pyridyl)-(2S)-2-pyrrolidinemethanol；[(2S)-1-pyridin-2-ylpyrrolidin-2-yl]methanol
• CAS: 199117-77-6
• 化学式: C₁₀H₁₄N₂O
• 分子量: 178.234
• InChiKey: CWTZVPOJPUXUKB-VIFPVBQESA-N

物化性质

• 沸点：
  337.1±12.0 °C(Predicted)
• 密度：
  1.144±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  36.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-(hydroxymethyl)-1-(pyridin-2-yl)pyrrolidine 在 copper(I) oxide 、 盐酸 、 氢溴酸 、 sodium acetate 、 铁粉 、 sodium hydride 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 2-imino-5-<4-<<1-(pyridin-2-yl)-(2S)-pyrrolidin-2-yl>methoxy>phenylmethyl>-4-thiazolidinone
  参考文献：
  名称：

  Novel Euglycemic and Hypolipidemic Agents. 4. Pyridyl- and Quinolinyl-Containing Thiazolidinediones

  摘要：

  A series of substituted pyridyl- and quinolinyl-containing 2,4-thiazolidinediones having interesting cyclic amine as a linker have been synthesized. Both unsaturated thiazolidinediones 5 and saturated thiazolidinediones 6 and their various salts were evaluated in db/db mice for euglycemic and hypolipidemic effects and compared with BRL compound 11 and BRL-49653, respectively. Some of the potent compounds were converted to various salts in order to obtain improved activities. Among all the salts evaluated, the maleate salt of unsaturated TZD 5a was found to be a very potent euglycemic and hypolipidemic compound. Some of the more interesting compounds have also been evaluated in ob/ob mice and compared with rosiglitazone (maleate salt of BRL-49653). Oral glucose tolerance tests were performed in both db/db and ob/ob mice. Pharmacokinetic studies of 5a maleate are also reported. Receptor binding studies of PPAR gamma by 5a/5a maleate did not show any significant transactivation of PPAR alpha or PPAR gamma.

  DOI：

  10.1021/jm980622j
• 作为产物：
  描述：

  2-(吡咯烷-1-基)吡啶 在 正丁基锂 、 [Rh(OH)(cod)]2 、 (11bR)-4-(((R)-2'-((triisopropylsilyl)oxy)-[1,1'-binaphthalen]-2-yl)oxy)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 47.0h， 生成 (S)-2-(hydroxymethyl)-1-(pyridin-2-yl)pyrrolidine
  参考文献：
  名称：

  铑催化对映选择性C(sp3)-H硼化不对称合成α-氨基硼酸酯

  摘要：

  α-氨基硼酸是α-氨基酸的同构硼类似物，由于含有这种结构的化合物在生物医学上的重要应用而受到广泛关注。此外，α-氨基硼酸通过多种碳-硼键转化作为合成中间体的固有多功能性使得这些化合物的有效合成非常理想。在这里，我们提出了一种 Rh-单亚磷酸酯手性催化体系，该体系能够对包括 2-(N-烷基氨基)杂芳基和 N-烷酰基或芳酰基在内的一系列底物类别的 N-相邻 C(sp3)-H 键进行高效的对映选择性硼基化-基仲或叔酰胺，其中一些是药剂或相关化合物。已经证明了对映体富集的 α-氨基硼酸盐的各种立体定向转化，包括 Suzuki-Miyaura 与芳基卤化物的偶联以及与 α-氨基酸的异氰酸酯衍生物的 Rh 催化反应，从而提供了一种新的肽链延长方法。作为这项工作的一个亮点，硼化方案成功地应用于催化剂控制的位点和立体选择性 C(sp3)-H 无保护二肽化合物的硼化反应，从而显着简化了抗癌药物分子硼替佐米的

  DOI：

  10.1021/jacs.9b12013

文献信息

• Heterocyclic compounds having antidiabetic, hypolipidaemic,
  申请人：Dr. Reddy's Research Foundation

  公开号：US05801173A1

  公开（公告）日：1998-09-01

  Novel antidiabetic compounds, their tautomeric forms, their derivatives, their steroisomers, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates and pharmaceuticaly acceptable compositions containing them; methods for preparing the antidiabetic compounds and their uses.

  新型抗糖尿病化合物，它们的互变异构体，它们的衍生物，它们的立体异构体，它们的多晶形态，它们的药学上可接受的盐，它们的药学上可接受的溶剂合物以及含有它们的药学上可接受的组合物；制备抗糖尿病化合物的方法及其用途。
• Design and Synthesis of Novel 1,3-Dioxane-2-carboxylic Acid Derivatives as PPAR&amp;#945;/&amp;#947; Dual Agonists
  作者：Harikishore Pingali、Mukul Jain、Shailesh Shah、Pankaj Makadia、Pandurang Zaware、Jeevankumar Jamili、Kalapatapu V.V.M. Sairam、Pravin Patil、Dinesh Suthar、Suresh Giri、Harilal Patel、Pankaj Patel

  DOI：10.2174/157018010791306533

  日期：2010.7.1

  1,3-dioxane carboxylic acid derivatives were prepared based on our previous studies directed towards identifying novel pharmacophore for the development of PPAR α/γ dual agonists. Based on the typical topology of PPAR agonists we focused our design approach on modifying lipophilic tail and prepared a series of compounds by replacing the oxazole moiety of our previously reported compound with optimized lipophilic groups. Compound 8a was found to be a weak PPAR activator but exhibited potent hypolipidemic and anti-hyperglycemic activities in vivo due to superior bioavailability, whereas 8f exhibited potent in vitro and invivo effects. The activity of 8f is further supported by molecular docking study.

  1,3- 二氧六环羧酸衍生物的制备基于我们之前的研究，这些研究旨在为 PPAR α/γ 双激动剂的开发确定新的药理基础。根据 PPAR 激动剂的典型拓扑结构，我们将设计方法的重点放在了亲脂性尾部的修饰上，并用优化的亲脂基团取代了之前报道的化合物中的噁唑分子，制备了一系列化合物。研究发现，化合物 8a 是一种弱 PPAR 激活剂，但由于其生物利用度较高，在体内表现出了强效的降血脂和降血糖活性，而 8f 则在体外和体内都表现出了强效作用。分子对接研究进一步证实了 8f 的活性。
• [EN] THIAZOLIDINEDIONE COMPOUNDS HAVING ANTIDIABETIC, HYPOLIPIDAEMIC, ANTIHYPERTENSIVE PROPERTIES, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS THEREOF<br/>[FR] COMPOSES DE THIAZOLIDINEDIONE PRESENTANT DES PROPRIETES ANTIDIABETIQUES, HYPOLIPIDEMIANTES, ANTIHYPERTENSIVES, LEUR PROCEDE DE PREPARATION ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：DR. REDDY'S RESEARCH FOUNDATION

  公开号：WO1997041120A1

  公开（公告）日：1997-11-06

  (EN) Novel thiazolidinedione antidiabetic compounds, their tautomeric forms, their derivatives, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates and pharmaceuticals acceptable compositions containing them; methods for preparing the antidiabetic compounds and their uses.(FR) L'invention concerne de nouveaux composés antidiabétiques de thiazolidinedione, leurs formes tautomères, leurs dérivés, leurs stéréoisomères, leurs polymorphes, leurs sels pharmaceutiquement acceptables, leurs solvates pharmaceutiquement acceptables et des compositions pharmaceutiquement acceptables les contenant, des procédés de préparation des composés antidiabétiques et leurs utilisations.

  (中) 一种新的噻唑烷酮类抗糖尿病化合物、它们的互变异构体、衍生物、立体异构体、多晶形态、药用可接受的盐、药用可接受的溶剂和含有它们的药用可接受的组合物；制备抗糖尿病化合物的方法及其用途。
• Lohray; Bhushan, Vidya; Sekar Reddy, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 4, p. 403 - 406
  作者：Lohray、Bhushan, Vidya、Sekar Reddy、Bheema Rao、Reddy, N. Jaipal、Reddy, K. Anantha、Vikramadithyan, Reeba K.、Rajagopalan

  DOI：——

  日期：——
• THIAZOLIDINEDIONE COMPOUNDS HAVING ANTIDIABETIC, HYPOLIPIDAEMIC, ANTIHYPERTENSIVE PROPERTIES, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS THEREOF
  申请人：DR. REDDY'S RESEARCH FOUNDATION

  公开号：EP0923580A1

  公开（公告）日：1999-06-23