3-(6-溴吡啶-3-基)丙-1-醇 | 656827-76-8

• 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
• 中文名称: 3-(6-溴吡啶-3-基)丙-1-醇
• 英文名称: 3-(6-bromo-3-pyridinyl)-1-propanol
• 英文别名: 3-(6-bromopyridin-3-yl)propan-1-ol
• CAS: 656827-76-8
• 化学式: C₈H₁₀BrNO
• 分子量: 216.077
• InChiKey: MXQCAFIUXXQSSI-UHFFFAOYSA-N

物化性质

• 沸点：
  336.6±27.0 °C(Predicted)
• 密度：
  1.483±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  3-(6-溴吡啶-3-基)丙-1-醇 在 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.59h， 生成
  参考文献：
  名称：

  Synthesis of a Non-Heme Template for Attaching Four Peptides:  An Approach to Artificial Iron(II)-Containing Peroxidases

  摘要：

  We are developing all-synthetic model cofactor-protein complexes in order to define the parameters controlling non-natural cofactor activity. The long-term objective is to establish the theoretical and practical basis for designing novel enzymes. A non-heme pentadentate ligand (N4Py) is being developed as a template for the site-specific attachment of a designed four-helix bundle. Previously, we attached two unprotected peptides via CH2Cl handles to N4Py. In the presence of hydrogen peroxide, the iron(II) complex of this ligand (2a) generates an (FeOOH)-O-III intermediate (3a) that can oxidize a wide variety of organic compounds. Here, we describe the synthesis of 27, a N4Py derivative in which four three-carbon spacers have been introduced, and show that four copies of an unprotected, single-cysteine peptide can be coupled via a thioether linkage to the ligand. In addition, a divergent synthesis route to tetrabromide ligand 1b has also been developed, providing the opportunity to prepare alternative pentadentate ligands efficiently by four cross-coupling reactions on a single molecule. Also, two of the four bromides of 1b can be selectively addressed by magnesium-bromide exchange.

  DOI：

  10.1021/jo035157z
• 作为产物：
  描述：

  2-溴-5-醛基吡啶 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 乙醚 为溶剂， 反应 1.84h， 生成 3-(6-溴吡啶-3-基)丙-1-醇
  参考文献：
  名称：

  Synthesis of a Non-Heme Template for Attaching Four Peptides:  An Approach to Artificial Iron(II)-Containing Peroxidases

  摘要：

  We are developing all-synthetic model cofactor-protein complexes in order to define the parameters controlling non-natural cofactor activity. The long-term objective is to establish the theoretical and practical basis for designing novel enzymes. A non-heme pentadentate ligand (N4Py) is being developed as a template for the site-specific attachment of a designed four-helix bundle. Previously, we attached two unprotected peptides via CH2Cl handles to N4Py. In the presence of hydrogen peroxide, the iron(II) complex of this ligand (2a) generates an (FeOOH)-O-III intermediate (3a) that can oxidize a wide variety of organic compounds. Here, we describe the synthesis of 27, a N4Py derivative in which four three-carbon spacers have been introduced, and show that four copies of an unprotected, single-cysteine peptide can be coupled via a thioether linkage to the ligand. In addition, a divergent synthesis route to tetrabromide ligand 1b has also been developed, providing the opportunity to prepare alternative pentadentate ligands efficiently by four cross-coupling reactions on a single molecule. Also, two of the four bromides of 1b can be selectively addressed by magnesium-bromide exchange.

  DOI：

  10.1021/jo035157z

文献信息

• Heteroaryl-substituted amides comprising a saturated linker group, and their use as pharmaceuticals
  申请人：Sanofi-Aventis Deutschland GmbH

  公开号：EP1741709A1

  公开（公告）日：2007-01-10

  The present invention relates to N-alkylamides of the formula I, in which A, Het, X, R1, R2 and R3 have the meanings indicated in the claims, which modulate the transcription of endothelial nitric oxide (NO) synthase and are valuable pharmacologically active compounds. Specifically, the compounds of the formula I upregulate the expression of the enzyme endothelial NO synthase and can be applied in conditions in which an increased expression of said enzyme or an increased NO level or the normalization of a decreased NO level is desired. The invention further relates to processes for the preparation of compounds of the formula I, to pharmaceutical compositions comprising them, and to the use of compounds of the formula I for the manufacture of a medicament for the stimulation of the expression of endothelial NO synthase or for the treatment of various diseases including cardiovascular disorders such as atherosclerosis, thrombosis, coronary artery disease, hypertension and cardiac insufficiency, for example.

  本发明涉及式I的N-烷基酰胺， 其中A、Het、X、R1、R2和R3的含义如权利要求中指出的，这些化合物能够调节内皮型一氧化氮（NO）合酶的转录，并且是有价值的药物活性化合物。具体而言，式I的化合物可以上调内皮型NO合酶的表达，并可用于那些需要增加所述酶的表达、增加NO水平或使降低的NO水平正常化的情况。本发明还涉及制备式I化合物的方法，包含它们的药物组合物，以及使用式I化合物用于制造刺激内皮型NO合酶表达或治疗包括动脉粥样硬化、血栓、冠心病、高血压和心力衰竭等各种疾病的药物。
• [EN] AZAINDAZOLE COMPOUNDS AS CCR1 RECEPTOR ANTAGONISTS<br/>[FR] COMPOSÉS AZAINDAZOLE EN TANT QU'ANTAGONISTES DES RÉCEPTEURS CCR1
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2010036632A1

  公开（公告）日：2010-04-01

  Disclosed are compounds of the formula (I), useful for treating a variety of diseases and disorders that are mediated or sustained through the activity of CCR1 including autoimmune diseases, such as rheumatoid arthritis and multiple sclerosis. Also disclosed are methods of making and methods of using same.

  公开的是化合物的公式（I），用于治疗通过CCR1活性介导或维持的多种疾病和疾病，包括自身免疫性疾病，如风湿性关节炎和多发性硬化症。还公开了制备方法和使用方法。
• [EN] INDAZOLE COMPOUNDS AS CCR1 RECEPTOR ANTAGONISTS<br/>[FR] COMPOSÉS INDAZOLE COMME ANTAGONISTES DES RÉCEPTEURS CCR1
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2009134666A1

  公开（公告）日：2009-11-05

  Disclosed indazoles compounds that are useful as antagonists of CCR1 activity and are thus useful for treating a variety of diseases and disorders that are mediated or sustained through the activity of CCR1 including autoimmune diseases, such as rheumatoid arthritis and multiple sclerosis. Also disclosed are pharmaceutical compositions comprising these compounds, methods of using these compounds in the treatment of various diseases and disorders, processes for preparing these compounds and intermediates useful in these processes.

  揭示了吲唑烯化合物，其作为CCR1活性拮抗剂是有用的，因此可用于治疗通过CCR1活性介导或维持的多种疾病和疾病，包括自身免疫疾病，如类风湿性关节炎和多发性硬化症。还披露了包含这些化合物的药物组合物，使用这些化合物治疗各种疾病和疾病的方法，制备这些化合物的过程以及在这些过程中有用的中间体。
• Heteroaryl-Substituted Amides Comprising A Saturated Linker Group, And Their Use As Pharmaceuticals
  申请人：STROBEL Harmut

  公开号：US20080171739A1

  公开（公告）日：2008-07-17

  The present invention relates to N-alkylamides of the formula I, in which A, Het, X, R 1 , R 2 and R 3 have the meanings indicated in the claims, which modulate the transcription of endothelial nitric oxide (NO) synthase and are valuable pharmacologically active compounds. Specifically, the compounds of the formula I upregulate the expression of the enzyme endothelial NO synthase and can be applied in conditions in which an increased expression of said enzyme or an increased NO level or the normalization of a decreased NO level is desired. The invention further relates to processes for the preparation of compounds of the formula I, to pharmaceutical compositions comprising them, and to the use of compounds of the formula I for the manufacture of a medicament for the stimulation of the expression of endothelial NO synthase or for the treatment of various diseases including cardiovascular disorders such as atherosclerosis, thrombosis, coronary artery disease, hypertension and cardiac insufficiency, for example.

  本发明涉及公式I的N-烷基酰胺，其中A，Het，X，R1，R2和R3具有所述声明中指示的含义，这些化合物调节内皮一氧化氮（NO）合酶的转录，并是有价值的药理活性化合物。具体地，公式I的化合物上调内皮一氧化氮合酶酶的表达，并可应用于需要增加该酶的表达或增加NO水平或规范降低的NO水平的情况。本发明还涉及制备公式I化合物的过程，包括它们的制药组合物，以及公式I化合物用于制造刺激内皮一氧化氮合酶表达或治疗各种疾病的药物的用途，包括心血管疾病，如动脉粥样硬化，血栓形成，冠状动脉疾病，高血压和心脏功能不全等。
• HETEROARYL-SUBSTITUTED AMIDES COMPRISING A SATURATED LINKER GROUP, AND THEIR USE AS PHARMACEUTICALS
  申请人：Sanofi-Aventis

  公开号：EP1899321A1

  公开（公告）日：2008-03-19