1-甲基-6-氧代-1,6-二氢吡啶-3-羰酰氯 | 162330-16-7

• 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
• 中文名称: 1-甲基-6-氧代-1,6-二氢吡啶-3-羰酰氯
• 英文名称: 1-methyl-6-oxo-1,6-dihydropyridine-3-carbonyl chloride
• 英文别名: 1-methyl-6-oxopyridine-3-carbonyl chloride
• CAS: 162330-16-7
• 化学式: C₇H₆ClNO₂
• 分子量: 171.583
• InChiKey: ASGHWERLCYSJLF-UHFFFAOYSA-N

物化性质

• 沸点：
  294.4±29.0 °C(Predicted)
• 密度：
  1.375±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-amino-N,N-diisopropylbenzamide 、 1-甲基-6-氧代-1,6-二氢吡啶-3-羰酰氯 以 二氯甲烷 为溶剂， 反应 0.25h， 以46%的产率得到N,N-diisopropyl-4-<(1,2-dihydro-1-methyl-2-oxopyridine-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-羧酸甲酯 在 氯化亚砜 、 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 1-甲基-6-氧代-1,6-二氢吡啶-3-羰酰氯
  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

• WO2019183587A5
  申请人：——

  公开号：WO2019183587A5

  公开（公告）日：2022-03-30
• Deady, Leslie W., Australian Journal of Chemistry, 1985, vol. 38, # 4, p. 637 - 641
  作者：Deady, Leslie W.

  DOI：——

  日期：——
• WO2020154571A5
  申请人：——

  公开号：WO2020154571A5

  公开（公告）日：2023-02-02
• COMPOUNDS AND USES THEREOF
  申请人：Yumanity Therapeutics, Inc.

  公开号：EP3768269A1

  公开（公告）日：2021-01-27
• [EN] COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS ET LEURS UTILISATIONS
  申请人：YUMANITY THERAPEUTICS INC

  公开号：WO2020198026A1

  公开（公告）日：2020-10-01

  The present invention features compounds useful in the treatment of neurological disorders and primary brain cancer. The compounds of the invention, alone or in combination with other pharmaceutically active agents, can be used for treating or preventing neurological disorders and primary brain cancer.

  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。