NSC 33350 | 6269-68-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: NSC 33350
• 英文别名: N-(4-amino-2-methyl-[6]quinolyl)-benzamide；N-(4-Amino-2-methyl-[6]chinolyl)-benzamid；4-Amino-6-(benzoyl)amino-2-methyl-quinoline；N-(4-Amino-2-methyl-6-quinolinyl)benzamide；N-(4-amino-2-methylquinolin-6-yl)benzamide
• CAS: 6269-68-7
• 化学式: C₁₇H₁₅N₃O
• 分子量: 277.326
• InChiKey: SBMGFSCRPGXVOV-UHFFFAOYSA-N

物化性质

• 熔点：
  251-252 °C
• 沸点：
  425.5±40.0 °C(Predicted)
• 密度：
  1.294±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  68
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4′-氨基乙酰苯胺 在 吡啶 、 盐酸 、 ammonium acetate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 37.17h， 生成 NSC 33350
  参考文献：
  名称：

  4-Aminoquinolines:  Novel Nociceptin Antagonists with Analgesic Activity

  摘要：

  Small-molecule nociceptin antagonists were synthesized to examine their therapeutic potential. After a 4-aminoquinoline derivative was found to bind with the human ORL1 receptor, a series of 4-aminoquinolines and related compounds were synthesized and their binding was evaluated. Elucidation of structure-activity relationships eventually led to the optimum compounds. One of the se compounds, N-(4-amino-2-methylquinolin-6-yl) -2-(4-ethylphenoxymethyl)benzamide hydrochloride (11) not only antagonized nociceptin-induced allodynia in mice but also showed analgesic effect in a hot plate test using mice and in a formalin test using rats. Its analgesic effect was not antagonized by the opioid antagonist naloxone. These results indicate that this nociceptin antagonist has the potential to become a novel type of analgesic that differs from mu -opioid agonists.

  DOI：

  10.1021/jm0002073

文献信息

• The Synthesis of Some 6-N-Substituted Amido Derivatives of 4,6-Diaminoquinaldine and a Study of their in vitro Antibacterial Activity^1,2
  作者：Chin-Tzu Peng、T. C. Daniels

  DOI：10.1021/ja01596a041

  日期：1956.8
• Substituted 4,6-diaminoquinolines as inhibitors of C5a receptor binding
  作者：Thomas J. Lanza、Philippe L. Durette、Thomas Rollins、Salvatore Siciliano、Dana N. Cianciarulo、Sumire V. Kobayashi、Charles G. Caldwell、Martin S. Springer、William K. Hagmann

  DOI：10.1021/jm00080a008

  日期：1992.1

  The anaphylatoxin C5a is implicated in a number of inflammatory diseases. It is a highly cationic protein with 13 of 74 amino acids being either arginine or lysine. A search focusing on positively charged molecules, particularly amine-containing functionalities, led to the discovery of substituted 4,6-diaminoquinolines 1 [N,N'-bis(4-amino-2-methyl-6-quinolyl)urea] and 7 [6-N-(2-chlorocinnamoyl)-4,6-diamino-2-methylquinoline) as inhibitors of C5a receptor binding. These two compounds inhibited the binding of radiolabeled C5a to its receptor isolated from human neutrophils with IC50's = 3.3 and 12-mu-g/mL, respectively. Our efforts to enhance their potencies by chemical modification revealed a narrow profile of potency for effective C5a receptor binding inhibition.
• US5919776A
  申请人：——

  公开号：US5919776A

  公开（公告）日：1999-07-06
• [EN] SUBSTITUTED AMINOQUINOLINES AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY<br/>[FR] AMINOQUINOLEINES SUBSTITUEES UTILISEES COMME MODULATEURS DE L'ACTIVITE DES RECEPTEURS DE LA CHEMOKINE
  申请人：MERCK & CO., INC.

  公开号：WO1998027815A1

  公开（公告）日：1998-07-02

  (EN) The present invention is directed to aminoquinolines of formula (I), (wherein R1, R2, R3 and R4 are defined herein) which are useful as modulators of chemokine receptor activity. In particular, these compounds are useful as modulators of the chemokine receptors CCR-1, CCR-2, CCR-2A, CCR-2B, CCR-3, CCR-4, CCR-5, CXCR-3 and/or CXCR-4.(FR) L'invention concerne des aminoquinoléines de formule (I) (dans laquelle R1, R2, R3 et R4 sont définis dans la description), utiles en tant que modulateurs de l'activité des récepteurs de la chémokine. Ces composés sont notamment utiles en tant que modulateurs des récepteurs de la chémokine CCR-1, CCR-2, CCR-2A, CCR-2B, CCR-3, CCR-4, CCR-5, CXCR-3 et/ou CXCR-4.
• 4-Aminoquinolines:  Novel Nociceptin Antagonists with Analgesic Activity
  作者：Hisashi Shinkai、Takao Ito、Tetsuya Iida、Yuki Kitao、Hideki Yamada、Itsuo Uchida

  DOI：10.1021/jm0002073

  日期：2000.11.1

  Small-molecule nociceptin antagonists were synthesized to examine their therapeutic potential. After a 4-aminoquinoline derivative was found to bind with the human ORL1 receptor, a series of 4-aminoquinolines and related compounds were synthesized and their binding was evaluated. Elucidation of structure-activity relationships eventually led to the optimum compounds. One of the se compounds, N-(4-amino-2-methylquinolin-6-yl) -2-(4-ethylphenoxymethyl)benzamide hydrochloride (11) not only antagonized nociceptin-induced allodynia in mice but also showed analgesic effect in a hot plate test using mice and in a formalin test using rats. Its analgesic effect was not antagonized by the opioid antagonist naloxone. These results indicate that this nociceptin antagonist has the potential to become a novel type of analgesic that differs from mu -opioid agonists.