(4-苯基吡啶-2-基)甲醇 | 55218-73-0

• 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: (4-苯基吡啶-2-基)甲醇
• 英文名称: 2-(hydroxymethyl)-4-phenylpyridine
• 英文别名: (4-phenylpyridin-2-yl)methanol；4-phenyl-2-pyridinemethanol
• CAS: 55218-73-0
• 化学式: C₁₂H₁₁NO
• 分子量: 185.225
• InChiKey: QPHORUBQDRBJEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933399090
• 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：

  (4-苯基吡啶-2-基)甲醇 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Inhibition of 1-Deoxy-d-Xylulose-5-Phosphate Reductoisomerase by Lipophilic Phosphonates: SAR, QSAR, and Crystallographic Studies

  摘要：

  1-Deoxy-D-xylulose-5-phosphate reductoisomerase (DXR) is a novel target for developing new antibacterial (including antituberculosis) and antimalaria drugs. Forty-one lipophilic phosphonates, representing a new class of DXR inhibitors, were synthesized, among which 5-phenylpyridin-2-ylmethylphosphonic acid possesses the most activity against E. coli DXR (EcDXR) with a K-i of 420 nM. Structure-activity relationships (SAR) are discussed, which can be rationalized using our EcDXR:inhibitor structures, and a predictive quantitative SAR (QSAR) model is also developed. Since inhibition studies of DXR from Mycobacterium tuberculosis (MtDXR) have not been performed well, 48 EcDXR inhibitors with a broad chemical diversity were found, however, to generally exhibit considerably reduced activity against MtDXR. The crystal structure of a, MtDXR:inhibitor complex reveals the flexible loop containing the residues 198-208 has no strong interactions with the 3,4-dichlorophenyl group of the inhibitor, representing a structural basis for the reduced activity. Overall, these results provide implications in the future design and development of potent DXR inhibitors.

  DOI：

  10.1021/jm200363d
• 作为产物：
  描述：

  4-苯基吡啶-2-羧酸甲酯 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 (4-苯基吡啶-2-基)甲醇
  参考文献：
  名称：

  结构定向鉴定吡啶-2-甲胺衍生物作为 MmpL3 抑制剂，用作抗结核药物

  摘要：

  分枝杆菌膜蛋白大 3 (MmpL3) 是一种内膜蛋白，在分枝杆菌酸的运输中发挥着至关重要的作用，而分枝杆菌酸对于结核分枝杆菌的生存至关重要，并且一直是新型抗结核药物的有前景的治疗靶点。在此，我们报告使用基于结构的药物设计策略发现了吡啶-2-甲胺抗结核化合物。化合物62是最有效的化合物，对支原体具有高活性。 tb 菌株 H37Rv (MIC = 0.016 μg/mL) 以及临床分离的 MDR/XDR-TB 菌株 (MIC = 0.0039–0.0625 μg/mL)，Vero 细胞毒性低 (IC 50 ≥ 16 μg /mL)，中等肝微粒体稳定性（CL int = 28 μL/min/mg）。此外，由于mmpL3中的单核苷酸多态性，S288T的抗性突变体对吡啶-2-甲胺62具有抗性，这表明化合物62可能是MmpL3的靶标。

  DOI：

  10.1016/j.ejmech.2023.115351

文献信息

• [EN] SPIROPYRROLIDINE BETA-SECRETASE INHIBITORS FOR THE TREATMENT OF ALZHEIMER'S DISEASE<br/>[FR] INHIBITEURS DE BÊTA-SÉCRÉTASE DE TYPE SPIROPYRROLIDINE POUR LE TRAITEMENT DE LA MALADIE D'ALZHEIMER
  申请人：MERCK SHARP & DOHME

  公开号：WO2010094242A1

  公开（公告）日：2010-08-26

  The present invention is directed to spiropyrrolidine compounds of formula (I) which are inhibitors of the beta-secretase enzyme and that are useful in the treatment of diseases in which the beta-secretase enzyme is involved, such as Alzheimer's disease. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the treatment of such diseases in which the beta-secretase enzyme is involved.

  本发明涉及式(I)的螺环吡咯烷化合物，它们是β-分泌酶的抑制剂，并且在治疗涉及β-分泌酶的疾病，如阿尔茨海默病中有用。该发明还涉及包含这些化合物的药物组合物，以及在治疗涉及β-分泌酶的这类疾病中使用这些化合物和组合物。
• 2-[(Phenylthio)methyl]pyridine derivatives: new antiinflammatory agents
  作者：Fortuna Haviv、Robert W. DeNet、Raymond J. Michaels、James D. Ratajczyk、George W. Carter、Patrick R. Young

  DOI：10.1021/jm00356a018

  日期：1983.2

  2-[(Phenylthio)methyl]pyridine derivatives inhibited the dermal reverse passive Arthus reaction (RPAR) in the rat. In the same model, indomethacin was inactive, and hydrocortisone was active. Compounds Ia-d also significantly reduced exudate volume and white blood cell accumulation in the pleural RPAR. This pattern of activity was similar to that of hydrocortisone and different from that of indomethacin

  2-[（（苯硫基）甲基]吡啶衍生物可抑制大鼠皮肤逆向被动Arthus反应（RPAR）。在同一模型中，消炎痛是无活性的，氢化可的松是有活性的。化合物Ia-d还显着减少了胸膜RPAR中的渗出液量和白细胞积聚。这种活性模式与氢化可的松相似，与消炎痛不同。
• Process for producing heterocyclic aldehyde
  申请人：Shiomi Yasuhiro

  公开号：US20050124807A1

  公开（公告）日：2005-06-09

  The present invention provides a process for preparing a heterocyclic aldehyde by oxidizing a heterocyclic alcohol with high selectivity and high yield. Specifically, the heterocyclic aldehyde is prepared by reacting a heterocyclic compound having at least one hydroxymethyl group bonded to a carbon atom of a heterocyclic ring with a hypohalogenous acid salt in the presence of a base to oxidize the hydroxymethyl group, wherein reaction is conducted in the co-presence of a 2,2,6,6-tetramethylpiperidine-1-oxyl derivative having at least two 2,2,6,6-tetramethylpiperidine-1-oxyl-4-yl groups.

  本发明提供了一种通过氧化具有高选择性和高产率的杂环醇来制备杂环醛的方法。具体来说，通过将至少有一个羟甲基基团与杂环环的碳原子键合的杂环化合物与次氯酸盐在碱的存在下反应，氧化羟甲基基团来制备杂环醛，其中反应在共存至少具有两个2,2,6,6-四甲基哌啶-1-氧基-4-基团的2,2,6,6-四甲基哌啶-1-氧基-4-基团的2,2,6,6-四甲基哌啶-1-氧基-4-基团的共存下进行。
• Photochemical C–H Silylation and Hydroxymethylation of Pyridines and Related Structures: Synthetic Scope and Mechanisms
  作者：Fatima Rammal、Di Gao、Sondes Boujnah、Aqeel A. Hussein、Jacques Lalevée、Annie-Claude Gaumont、Fabrice Morlet-Savary、Sami Lakhdar

  DOI：10.1021/acscatal.0c03726

  日期：2020.11.20

  Considering the synthetic relevance of heteroarenes in various areas ranging from organic synthesis to medicinal chemistry, developing practically simple methodologies to access functionalized heteroarenes is of a significant value. Described herein is an efficient approach for C–H silylation and hydroxymethylation of pyridines and related heterocycles by the combination of silanes or methanol with readily

  考虑到杂芳烃在从有机合成到药物化学的各个领域中的合成相关性，开发实用的简单方法来获得官能化的杂芳烃具有重要价值。本文描述的是通过硅烷或甲醇与易于获得的N的组合进行吡啶和相关杂环的CH甲硅烷基化和羟甲基化的有效方法在蓝光下具有低催化剂负载量（2摩尔％）的-甲氧基吡啶鎓离子。生物学相关化合物的合成证明了已开发反应的合成重要性。电子顺磁共振光谱，量子产率测量和密度泛函理论计算使我们能够了解两种光催化反应的反应机理。
• Electrochemical reduction of pyridine carboxamide bases
  申请人：Reilly Tar & Chemical Corporation

  公开号：US04695352A1

  公开（公告）日：1987-09-22

  Electrochemical reductions of pyridine carboxamide bases performed by electrolysis in a divided flow cell utilizing an ion-exchange membrane at a high hydrogen-overvoltage cathode and in an aqueous or partly aqueous medium comprising a Lowry-Bronsted acid in at least a 1:1 equivalent ratio with the pyridine carboxamide base. A titanium salt catalyst and other means are disclosed to add selectivity to the reduction and improve yield of the amine or other desired reaction product. With all bases, significant advantages of a commercial and industrial nature are reported over prior art static, beaker cell technology.

  利用离子交换膜在分流电池中进行吡啶羧酰胺碱的电化学还原，使用高过氢电位阴极，在至少1：1当量比例下，以含有Lowry-Bronsted酸的水或部分水介质中进行。透露了钛盐催化剂和其他手段，以增加还原的选择性并提高胺或其他所需反应产物的产率。针对所有碱，相比先前的静态烧杯电池技术，报告了商业和工业上的显着优势。