1-甲基-6-氧代哌啶-3-羧酸 | 22540-51-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 1-甲基-6-氧代哌啶-3-羧酸
• 英文名称: 1-methyl-6-oxopiperidine-3-carboxylic acid
• CAS: 22540-51-8
• 化学式: C₇H₁₁NO₃
• 分子量: 157.169
• InChiKey: FMLCUICPLLRLEU-UHFFFAOYSA-N

物化性质

• 沸点：
  366.2±35.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933790090

反应信息

• 作为反应物：
  描述：

  1-甲基-6-氧代哌啶-3-羧酸 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 0.42h， 生成 N-tert-butyl-4-<(1-methyl-2-oxopiperidine-5-yl)amido>benzamide
  参考文献：
  名称：

  Novel 5α-reductase inhibitors. Synthesis and structure-activity studies of 5-substituted 1-methyl-2-pyridones and 1-methyl-2-piperidones

  摘要：

  In search for nonsteroidal inhibitors of 5 alpha-reductase for the treatment of benign prostatic hyperplasia (BPH) and possibly prostate cancer, substrate mimicks were synthesized comprising of a 1-methyl-2-pyridone (2, 4-16) or 1-methyl-2-piperidone (1, 3, 17-22) moiety (mimicking steroidal ring A) and a diisopropyl (1, 2, (E)-5-(E)-7, (Z)-5-(Z)-7, 11-13, 17-19) or a tert-butyl (3, 4, (E)-8-(E)-10, (Z)-8(Z)-10, 14-16, 20-22) benzamide (mimicking steroidal ring D). The bridge connecting the 5 and 4 positions of the rings consisted of amide (CONH: 1-4), ethenyl (CH=CH, CCH3=CH, CH=CH3: (E)-5-(E)-10, (Z)-5(Z)-10) or ethylene groups (CH2CH2, CHCH3CH2, CH2CHCH3: 11-22). The amides 1-4 were obtained by amidation of the carboxylic acid chlorides with the 4-amino-N-substituted benzamides. The ethenyl compounds (E)-5(E)-10 and (Z)-5-(Z)-10 were synthesized by Wittig reaction of the carbonyl compounds and the corresponding triphenylphosphonium salts and subsequent separation of the stereoisomers. Depending on the time of reaction, catalytic hydrogenation of the ethenyl isomers (E)-5-(E)-10 led to the pyridone-substituted ethylene compounds 11-16 as well as to the piperidone-substituted ethylene compounds 17-22. The 5 alpha-reductase inhibitory properties were determined using rat ventral prostate, as well as human BPH and prostate cancer as source, 1 beta,2 beta-[H-3]testosterone as substrate and a HPLC procedure for the separation of dihydrotestosterone (DHT). Tested at a concentration of 100 mu M, the inhibition values of 1-22 ranged from 0-99%. Significant differences were observed between rat and human enzyme. The most active compound was N,N-diisopropyl-4-[2-(1-methyl-2-oxo-piperidine-5-yl)ethylene]benzamide 17 (IC50: 13 mu M).

  DOI：

  10.1016/0223-5234(94)90104-x
• 作为产物：
  描述：

  1-甲基-6-氧代-1,6-二氢吡啶-3-羧酸 在 platinum(IV) oxide 、 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 1-甲基-6-氧代哌啶-3-羧酸
  参考文献：
  名称：

  [EN] COMPOUNDS AND USES THEREOF
  [FR] COMPOSÉS ET LEURS UTILISATIONS

  摘要：

  本发明涉及对神经系统疾病和原发性脑癌治疗中有用的化合物。本发明的化合物，单独或与其他药用活性剂结合使用，可用于治疗或预防神经系统疾病和原发性脑癌。

  公开号：

  WO2020198026A1

文献信息

• [EN] AZETIDIN-3-YLMETHANOL DERIVATIVES AS CCR6 RECEPTOR MODULATORS<br/>[FR] DÉRIVÉS D'AZÉTIDIN-3-YLMÉTHANOL EN TANT QUE MODULATEURS DU RÉCEPTEUR CCR6
  申请人：IDORSIA PHARMACEUTICALS LTD

  公开号：WO2021219849A1

  公开（公告）日：2021-11-04

  The present invention relates to compounds of Formula (I), their synthesis and use as CCR6 receptor modulators for the treatment or prevention of various diseases, conditions or disorders.

  本发明涉及式(I)化合物，其合成以及作为CCR6受体调节剂用于治疗或预防各种疾病、状况或障碍。
• 6.5 -PYRROLOPIPERIDINE TACHYKININ RECEPTOR ANTAGONISTS
  申请人：Bao Jianming

  公开号：US20100197724A1

  公开（公告）日：2010-08-05

  The present invention is directed to certain hydroxymethyl ether hydroisoindoline compounds which are useful as neurokinin-1 (NK-1) receptor antagonists, and inhibitors of tachykinin and in particular substance P. The invention is also concerned with pharmaceutical formulations comprising these compounds as active ingredients and the use of the compounds and their formulations in the treatment of certain disorders, including emesis, urinary incontinence, LUTS, depression, and anxiety.

  本发明涉及某些羟甲基醚羟异吲哚化合物，其可用作神经激肽-1（NK-1）受体拮抗剂，以及缓激肽和特别是P物质的抑制剂。该发明还涉及包含这些化合物作为活性成分的药物配方，以及这些化合物及其配方在治疗某些疾病，包括呕吐、尿失禁、下尿路症状、抑郁症和焦虑症中的用途。
• Substituted benzimidazole derivatives as melanocortin 4 receptor antagonists
  申请人：Santhera Pharmaceuticals (Schweiz) AG

  公开号：EP2439197A1

  公开（公告）日：2012-04-11

  The present invention relates to substituted benzimidazole derivatives as melanocortin-4 receptor (MC-4R) modulators.

  本发明涉及取代苯并咪唑衍生物作为黑色素皮质素-4受体（MC-4R）调节剂。
• [EN] FERROPTOSIS INHIBITORS–DIARYLAMINE PARA-ACETAMIDES<br/>[FR] INHIBITEURS DE FERROPTOSE-DIARYLAMINE PARA-ACÉTAMIDES
  申请人：SIRONAX LTD

  公开号：WO2021175200A1

  公开（公告）日：2021-09-10

  Provided are compounds that inhibit ferroptosis activity, or modulate or inhibit a disease associated with ferroptosis dysregulation, such as neuropathy, ischemia reperfusion injury, acute kidney failure and cancer, including corresponding sulfonamides, and pharmaceutically acceptable salts, hydrates and stereoisomers thereof. The compounds are employed in pharmaceutical compositions, and methods of making and use, including treating a person in need thereof with an effective amount of the compound or composition, and detecting a resultant improvement in the person's health or condition.

  提供了抑制铁死亡活性的化合物，或调节或抑制与铁死亡失调相关的疾病，如神经病、缺血再灌注损伤、急性肾衰竭和癌症，包括相应的磺胺类化合物，以及其药用可接受的盐、水合物和立体异构体。这些化合物用于制备药物组合物，并且用于制备和使用方法，包括以有效剂量的化合物或组合物治疗需要的人，并检测人的健康或状况的改善。
• Discovery of a Highly Selective BET BD2 Inhibitor from a DNA-Encoded Library Technology Screening Hit
  作者：Francesco Rianjongdee、Stephen J. Atkinson、Chun-wa Chung、Paola Grandi、James R. J. Gray、Laura J. Kaushansky、Patricia Medeiros、Cassie Messenger、Alex Phillipou、Alex Preston、Rab K. Prinjha、Inmaculada Rioja、Alexander L. Satz、Simon Taylor、Ian D. Wall、Robert J. Watson、Gang Yao、Emmanuel H. Demont

  DOI：10.1021/acs.jmedchem.1c00412

  日期：2021.8.12

  Second-generation bromodomain and extra terminal (BET) inhibitors, which selectively target one of the two bromodomains in the BET proteins, have begun to emerge in the literature. These inhibitors aim to help determine the roles and functions of each domain and assess whether they can demonstrate an improved safety profile in clinical settings compared to pan-BET inhibitors. Herein, we describe the discovery of a

  文献中开始出现第二代溴结构域和额外末端 (BET) 抑制剂，它们选择性地靶向 BET 蛋白中的两个溴结构域之一。这些抑制剂旨在帮助确定每个域的作用和功能，并评估与 pan-BET 抑制剂相比，它们是否可以在临床环境中显示出更好的安全性。在此，我们描述了一种新的 BET BD2 选择性化学型的发现，使用基于结构的药物设计从 DNA 编码文库技术鉴定的命中中发现，显示与先前报道的 100 倍以上 BD2 选择性化学型 GSK620 的关键结构差异、GSK046 和 ABBV-744。根据对系列物理化学性质的选择性和优化的基于结构的假设，我们确定了60(GSK040)，一种体外即用和体内能力的 BET BD2 抑制剂，对 BET BD1 具有前所未有的选择性（5000 倍），对其他溴结构域的选择性极佳，并且具有良好的物理化学性质。这种新型化学探针可以添加到表观遗传学研究进展中使用的工具箱中。