5-Benzylamino-2-phenyl-4-cyanooxazol | 64326-59-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-Benzylamino-2-phenyl-4-cyanooxazol
• 英文别名: 5-benzylamino-2-phenyl-oxazole-4-carbonitrile；5-(Benzylamino)-2-phenyl-1,3-oxazole-4-carbonitrile
• CAS: 64326-59-6
• 化学式: C₁₇H₁₃N₃O
• mdl: MFCD00411993
• 分子量: 275.31
• InChiKey: DWENCHAKPUPSCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  61.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-Benzylamino-2-phenyl-4-cyanooxazol 在 一水合肼 作用下， 以 乙二醇 为溶剂， 反应 3.0h， 以70%的产率得到N-[5-amino-3-(benzylamino)-1H-pyrazol-4-yl]benzamide
  参考文献：
  名称：

  Transformation of substituted 5-amino-1,3-oxazole-4-carbonitriles into new 3,4,5-triaminopyrazole derivatives

  摘要：

  Reactions of accessible 5-alkylamino- and 5-arylamino-1,3-oxazole-4-carbonitriles with hydrazine hydrate on heating involved a complex transformation sequence resulting in the formation of 3,4,5-triaminopyrazole derivatives. The structure of the products was confirmed by their cyclocondensation with acetylacetone, leading to 2-alkyl(aryl)amino-3-acylamino-5,7-dimethylpyrazolo[1,5-a]pyrimidines which were identified by NMR spectroscopy using COSY, NOESY, HMQC, and HMBC techniques.

  DOI：

  10.1134/s1070363210010172
• 作为产物：
  描述：

  2-benzoylamino-3,3-dichloroacrylonitrile 、 苄胺 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 5-Benzylamino-2-phenyl-4-cyanooxazol
  参考文献：
  名称：

  新型N-(4-氰基-1,3-恶唑-5-基)磺酰胺衍生物的合成、表征及其针对NCI-60癌细胞系的体外活性筛选

  摘要：

  合成了一系列 14 种新型磺酰胺 - 1,3-恶唑衍生物，并针对 NCI 60 癌细胞系进行了研究。对化合物 2 和 10 进行比较分析，并考虑与 L-半胱氨酸类似物 (r=0.57) 和美他辛 (r=0.53) 的中度相关性。鉴于积极的抗癌效果，N-(4-氰基-1,3-恶唑-5-基)-磺酰胺有望进一步功能化以获得更具活性的化合物。

  DOI：

  10.1002/cmdc.202300527

文献信息

• A facile synthesis of new 1,2‐dihydro‐2λ⁵‐[1,3]oxazolo[5,4‐<i>d</i>][1,3,2]diazaphosphinine derivatives starting from 2‐benzoylamino‐3, 3‐dichloroacrylonitrile
  作者：Oleg V. Shablykin、Andrei A. Gakh、Vladimir S. Brovarets、Eduard B. Rusanov、Boris S. Drach

  DOI：10.1002/hc.20470

  日期：2008.7

  Easily accessible 2-benzoylamino-3,3-dichloroacrylonitrile, when treated successively with primary amines, phosphorus pentachloride, sulfur dioxide, and various N- or S-nucleophiles, furnishes the corresponding derivatives of 1,2-dihydro-2lambda}sup 5}-[1,3]oxazolo[5,4-d][1,3,2]diazaphosphinine, a novel fused heterocycle. The structure of the compounds obtained is unequivocally confirmed by spectroscopic

  容易获得的 2-苯甲酰氨基-3,3-二氯丙烯腈，当依次用伯胺、五氯化磷、二氧化硫和各种 N-或 S-亲核试剂处理时，可提供 1,2-二氢-2λ}λ} sup 5}-[1,3] 恶唑并​​[5,4-d][1,3,2]二氮杂膦，一种新型稠合杂环。所得化合物的结构通过光谱方法和 X 射线衍射分析得到明确证实。
• Drach,B.S.; Mis'kevich,G.N., Journal of Organic Chemistry USSR (English Translation), 1977, vol. 13, p. 1283 - 1289
  作者：Drach,B.S.、Mis'kevich,G.N.

  DOI：——

  日期：——
• DRACH B. S.; MISKEVICH G. N., ZH. ORGAN. XIMII, 1977, 13, HO 7, 1398-1404
  作者：DRACH B. S.、 MISKEVICH G. N.

  DOI：——

  日期：——
• Transformation of substituted 5-amino-1,3-oxazole-4-carbonitriles into new 3,4,5-triaminopyrazole derivatives
  作者：A. P. Kozachenko、O. V. Shablykin、A. N. Vasilenko、V. S. Brovarets

  DOI：10.1134/s1070363210010172

  日期：2010.1

  Reactions of accessible 5-alkylamino- and 5-arylamino-1,3-oxazole-4-carbonitriles with hydrazine hydrate on heating involved a complex transformation sequence resulting in the formation of 3,4,5-triaminopyrazole derivatives. The structure of the products was confirmed by their cyclocondensation with acetylacetone, leading to 2-alkyl(aryl)amino-3-acylamino-5,7-dimethylpyrazolo[1,5-a]pyrimidines which were identified by NMR spectroscopy using COSY, NOESY, HMQC, and HMBC techniques.
• Synthesis, characterization of novel N‐(4‐cyano‐1,3‐oxazol‐5‐yl)sulfonamide derivatives and in vitro screening their activity against NCI‐60 cancer cell lines
  作者：Oleksandr Severin、Stepan Pilyo、Maryna Kachaeva、Victor Zhirnov、Diana Hodyna、Oksana Bahrieieva、Volodymyr Brovarets

  DOI：10.1002/cmdc.202300527

  日期：2024.3

  A series of 14 new sulfonylamides – 1,3-oxazole derivatives are synthesized and investigated against NCI 60 cancer cell lines. COMPARE analysis is conducted for compounds 2 and 10 and considering moderate correlation with the L-cysteine analog (r=0.57) and maytasine (r=0.53). In view of the positive anticancer results, N-(4-cyano-1,3-oxazol-5-yl)-sulfonamides may be promising for further functionalization

  合成了一系列 14 种新型磺酰胺 - 1,3-恶唑衍生物，并针对 NCI 60 癌细胞系进行了研究。对化合物 2 和 10 进行比较分析，并考虑与 L-半胱氨酸类似物 (r=0.57) 和美他辛 (r=0.53) 的中度相关性。鉴于积极的抗癌效果，N-(4-氰基-1,3-恶唑-5-基)-磺酰胺有望进一步功能化以获得更具活性的化合物。