1-苯基-N-(1,3-噻唑-2-基甲基)甲胺 | 247235-78-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-苯基-N-(1,3-噻唑-2-基甲基)甲胺
• 中文别名: 苄基-(噻唑-2-基甲基)胺；1-苯基-N-(2-噻唑基甲基)甲胺；1-苯基-N-(1,3-噻唑-2-基甲基)甲胺二盐酸盐；1-苯基-N-(噻唑-2-基甲基)甲胺
• 英文名称: N-(thiazol-2-ylmethyl)benzylamine
• 英文别名: N-benzyl-2-aminomethylthiazole；1-phenyl-N-(1,3-thiazol-2-ylmethyl)methanamine
• CAS: 247235-78-5
• 化学式: C₁₁H₁₂N₂S
• mdl: MFCD19442235
• 分子量: 204.296
• InChiKey: UFWSEPMUQJPVBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2934100090

反应信息

• 作为反应物：
  描述：

  1-苯基-N-(1,3-噻唑-2-基甲基)甲胺 在 sodium hydroxide 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 28.0h， 生成
  参考文献：
  名称：

  Second-Generation Peptidomimetic Inhibitors of Protein Farnesyltransferase Demonstrating Improved Cellular Potency and Significant in Vivo Efficacy

  摘要：

  The synthesis and evaluation of analogues of previously reported farnesyltransferase inhibitors, pyridyl benzyl ether 3 and pyridylbenzylamine 4, are described. Substitution of 3 at the 5-position of the core aryl ring resulted in inhibitors of equal or less potency against the enzyme and decreased efficacy in a cellular assay against Ras processing by the enzyme. Substitution of 4 at the benzyl nitrogen yielded 26, which showed improved efficacy and potency and yet presented a poor pharmacokinetic profile. Further modification afforded 30, which demonstrated a dramatically improved pharmacokinetic profile. Compounds 26 and 29 demonstrated significant in vivo efficacy in nude mice inoculated with MiaPaCa-2, a human pancreatic tumorderived cell line.

  DOI：

  10.1021/jm9901935
• 作为产物：
  描述：

  N-苄基-1-(噻唑-2-基)甲亚胺 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 1-苯基-N-(1,3-噻唑-2-基甲基)甲胺
  参考文献：
  名称：

  Second-Generation Peptidomimetic Inhibitors of Protein Farnesyltransferase Demonstrating Improved Cellular Potency and Significant in Vivo Efficacy

  摘要：

  The synthesis and evaluation of analogues of previously reported farnesyltransferase inhibitors, pyridyl benzyl ether 3 and pyridylbenzylamine 4, are described. Substitution of 3 at the 5-position of the core aryl ring resulted in inhibitors of equal or less potency against the enzyme and decreased efficacy in a cellular assay against Ras processing by the enzyme. Substitution of 4 at the benzyl nitrogen yielded 26, which showed improved efficacy and potency and yet presented a poor pharmacokinetic profile. Further modification afforded 30, which demonstrated a dramatically improved pharmacokinetic profile. Compounds 26 and 29 demonstrated significant in vivo efficacy in nude mice inoculated with MiaPaCa-2, a human pancreatic tumorderived cell line.

  DOI：

  10.1021/jm9901935

文献信息

• Synthesis of new thiazole-2, -4, and -5-yl-(amino)methylphosphonates and phosphinates: unprecedented cleavage of thiazole-2 derivatives under acidic conditions
  作者：Tomasz Krzysztof Olszewski、Bogdan Boduszek

  DOI：10.1016/j.tet.2010.09.026

  日期：2010.11

  An efficient and reliable synthesis of new thiazole-(amino)methylphosphonic, phosphinic acids, and phosphine oxides is reported. The synthetic protocol is based on nucleophilic addition of phosphorous species to thiazole derived imines. Unexpectedly, it was discovered that heating of thiazole-2-yl-(amino)methylphosphonates and phosphinates with aqueous HCl leads to their decomposition resulting in

  报道了新的噻唑-（氨基）甲基膦酸，次膦酸和氧化膦的高效可靠合成。合成规程基于将磷物质亲核加成到噻唑衍生的亚胺中。出乎意料的是，发现噻唑-2-基-（氨基）甲基膦酸酯和次膦酸酯与HCl水溶液一起加热会导致它们分解，导致C-P键断裂，排斥含磷片段并形成相应的仲N-（噻唑-2-基-甲基）-烷基胺。提出了用于这种切割的两种替代机制。
• Inhibitors of protein isoprenyl transferases
  申请人：Abbott Laboratories

  公开号：US06277871B1

  公开（公告）日：2001-08-21

  The present invention relates to novel compounds of Formula I which are useful in inhibiting protein isoprenyl transferases and the farnesylation or geranylgeranylation of the oncogene protein Ras and other related small g-proteins, and compositions containing such compounds and methods of using such compounds.

  本发明涉及一种新的I式化合物，可用于抑制蛋白异戊烯基转移酶和癌基因蛋白Ras及其他相关小G蛋白的法尼酰化或戊二烯基化，以及含有此类化合物的组合物和使用此类化合物的方法。
• 5-HETEROYL INDOLE DERIVATIVES
  申请人：PFIZER INC.

  公开号：EP0571471A1

  公开（公告）日：1993-12-01
• US6277871B1
  申请人：——

  公开号：US6277871B1

  公开（公告）日：2001-08-21