N-[(E)-1-quinolin-2-ylethylideneamino]-1,3-benzothiazol-2-amine

• 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: N-[(E)-1-quinolin-2-ylethylideneamino]-1,3-benzothiazol-2-amine
• 化学式: C₁₈H₁₄N₄S
• 分子量: 318.402
• InChiKey: YNGWHJOBGXTPJZ-CIAFOILYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  78.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(喹啉-2-基)乙酮 、 2-肼基苯并噻唑 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 以76%的产率得到N-[(E)-1-quinolin-2-ylethylideneamino]-1,3-benzothiazol-2-amine
  参考文献：
  名称：

  Thiazolyl and benzothiazolyl hydrazones derived from α-(N)-acetylpyridines and diazines: synthesis, antiproliferative activity and CoMFA studies

  摘要：

  The synthesis of a series of thiazolyl and benzothiazolyl hydrazones derived from alpha-(N)-acylpyridines,-quinolines, -isoquinolines, -pyridazines, -pyrimidines, and -pyrazines is reported. The stereochemistry of these compounds was determined by NMR spectroscopic methods. The antiproliferative activity of the novel compounds was quantified in tissue culture (melanoma, breast carcinoma, colon adenocarcinoma, epitheloid cervix carcinoma, Burkitt's lymphoma, leukemia, and hydroxyurea sensitive and resistant myelogenous leukemia sublines). All compounds exhibited profound antiproliferative activity, in particular against Burkitt's lymphoma cells. Out of this series, compounds 6b, 7b, 7c, 8c and 8i were found to be 13-900 times more potent than hydroxyurea and no cross-resistance to hydroxyurea was observed. A predictive 3D-QSAR model using the CoMFA approach was established.

  DOI：

  10.1016/s0223-5234(97)81677-7

文献信息

• Thiazolyl and benzothiazolyl hydrazones derived from α-(N)-acetylpyridines and diazines: synthesis, antiproliferative activity and CoMFA studies
  作者：J Easmon、G Heinisch、J Hofmann、T Langer、HH Grunicke、J Fink、G Pürstinger

  DOI：10.1016/s0223-5234(97)81677-7

  日期：1997.5

  The synthesis of a series of thiazolyl and benzothiazolyl hydrazones derived from alpha-(N)-acylpyridines,-quinolines, -isoquinolines, -pyridazines, -pyrimidines, and -pyrazines is reported. The stereochemistry of these compounds was determined by NMR spectroscopic methods. The antiproliferative activity of the novel compounds was quantified in tissue culture (melanoma, breast carcinoma, colon adenocarcinoma, epitheloid cervix carcinoma, Burkitt's lymphoma, leukemia, and hydroxyurea sensitive and resistant myelogenous leukemia sublines). All compounds exhibited profound antiproliferative activity, in particular against Burkitt's lymphoma cells. Out of this series, compounds 6b, 7b, 7c, 8c and 8i were found to be 13-900 times more potent than hydroxyurea and no cross-resistance to hydroxyurea was observed. A predictive 3D-QSAR model using the CoMFA approach was established.