2'-(2-Aminoethyl)-2,4'-bithiazole-4-carboxylic acid | 30760-84-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2'-(2-Aminoethyl)-2,4'-bithiazole-4-carboxylic acid
• 英文别名: 2-[2-(2-Aminoethyl)-1,3-thiazol-4-yl]-1,3-thiazole-4-carboxylic acid
• CAS: 30760-84-0
• 化学式: C₉H₉N₃O₂S₂
• 分子量: 255.321
• InChiKey: CQYQBMRDUAGCGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  146
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2'-(2-Aminoethyl)-2,4'-bithiazole-4-carboxylic acid 在 氯化亚砜 、 (CH₃)2N(C₆H₄N) 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 21.5h， 生成 N-(3-bromopropyl)-2-[2-[2-[(2,2,2-trifluoroacetyl)amino]ethyl]-1,3-thiazol-4-yl]-1,3-thiazole-4-carboxamide
  参考文献：
  名称：

  Bleomycin: synthesis and structural verification of the tripeptide S and tetrapeptide S moieties

  摘要：

  DOI：

  10.1021/ja00524a055
• 作为产物：
  描述：

  methyl 2-(2-bromoacetyl)thiazole-4-carboxylate 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 15.0h， 生成 2'-(2-Aminoethyl)-2,4'-bithiazole-4-carboxylic acid
  参考文献：
  名称：

  Total Synthesis of Bleomycin A2 and Related Agents. 1. Synthesis and DNA Binding Properties of the Extended C-Terminus: Tripeptide S, Tetrapeptide S, Pentapeptide S, and Related Agents

  摘要：

  Full details of concise, diastereocontrolled syntheses of 2-5 and their incorporation into tri-, tetra-, and pentapeptide S, the C-terminus of bleomycin Alt are described. The extension of the studies to the synthesis of a complete set of tri- and tetrapeptide S structural analogs 29a,b and 43b-j is detailed, and their DNA binding constants (apparent K-B, calf thymus DNA) and apparent binding site sizes were determined. Consistent with past observations, the studies highlight the fact that the majority of the DNA binding affinity for bleomycin A(2) (1.0 X 10(5) M(-1)) and deglycobleomycin Aa (1.1 x 10(5) M(-1)) is embodied within N-BOC-tripeptide S (0.26 X 10(5) M(-1)). The additional comparisons of 29a (O.18 x 10(5) M(-1)), N-BOC-tetrapeptide S (0.21 x 10(5) M(-1)), 43h (0.20 x 10(5) M(-1)), and N-BOC-pentapeptide S (0.23 X 10(5) M(-1)) versus N-BOC-dipeptide S (0.10 x 10(5) M(-1)) indicate productive stabilizing binding interactions for the tripeptide S L-threonine subunit and substituent, illustrate that the entire pentanoic acid subunit of tetrapeptide S and its substituents do not significantly contribute to DNA binding affinity, and indicate that the entire beta-hydroxy-L-histidine subunit of pentapeptide S does not contribute to DNA binding affinity. With the exception of the L-threonine side chain substituent, the observations suggest that the tri- and tetrapeptide S substituent effects on the bleomycin A(2) DNA cleavage reaction are not due to substantial stabilizing binding interactions with duplex DNA. In addition, the measured apparent binding site sizes for bleomycin A(2)(3.8 base pairs), deglycobleomycin A(2) (3.9 base pairs), N-BOC-tripeptide S (3.6 base pairs), N-BOC-tetrapeptide S (3.7 base pairs), 43h (3.5 base pairs), and N-BOC-pentapeptide S (4.2 base pairs) versus N-BOC-dipeptide S (2.2 base pairs) and 29a (2.7 base pairs) suggest that it is the tripeptide S subunit of bleomycin A(2) that is fully bound to duplex DNA, that the tripeptide S L-threonine hydroxyethyl substituent detectably affects the agent interaction with duplex DNA, but that the presence or absence of the other tetrapeptide S and pentapeptide S backbone substituents do not substantially alter the binding site size or tripeptide S binding mode.

  DOI：

  10.1021/ja00092a011

文献信息

• Synthesis and properties of some derivatives of thiazolecarboxylic amino acids
  作者：G. P. Andronnikova、T. é. Pavlovskaya、Z. V. Pushkareva

  DOI：10.1007/bf00758776

  日期：1975.6

  the synthesis of compounds III-V, which result from the transformation of the carboxylic group in acid I. A study was made of the extent to which these compounds suppressed the synthesis of nucleic acids in vitro; a culture of strain NK/Ly of lympholeukosis was used. For comparison we also synthesized derivatives (IIIaVa) of a sample Ia, namely 2-(B-aminoethyl)thiazole-4-carboxylic acid (II), because

  在这里，我们描述了化合物 III-V 的合成，这是由酸 I 中羧基的转化产生的。研究了这些化合物在体外抑制核酸合成的程度；使用了淋巴细胞白血病NK/Ly菌株的培养物。为了比较，我们还合成了样品 Ia 的衍生物（IIIaVa），即 2-（B-氨基乙基）噻唑-4-羧酸（II），因为已知（氨基烷基）噻唑羧酸包含在某些抗生素[3]。氨基对邻苯二甲酰衍生物的脱酰作用通过[4]中描述的方法进行。
• Total synthesis of deglyco-bleomycin A2
  作者：Tomohisa Takita、Yoji Umezawa、Sei-ichi Saito、Hajime Morishima、Hamao Umezawa、Yasuhiko Muraoka、Masanobu Suzuki、Masami Otsuka、Susumu Kobayashi、Masaji Ohno

  DOI：10.1016/s0040-4039(01)92519-5

  日期：1981.1

  Deglyco-bleomycin A2, the aglycon of bleomycin A2, has been synthesized for the first time.

  Deglyco-bleomycin A2（博来霉素A2的糖苷配基）是首次合成。
• Novel 3-(4'-aminobutylamino)-propylamino-bleomycin derivatives, a process for their preparation and their use as medicaments
  申请人：MICROBIAL CHEMISTRY RESEARCH FOUNDATION

  公开号：EP0135675A1

  公开（公告）日：1985-04-03

  The present invention relates to novel 3-(4'-aminobutylamino)propylamino-bleomycin derivatives and a process for their preparation. The compounds of the invention show carcinostatic properties and can, therefor, be used as medicaments.

  本发明涉及新型 3-(4'-氨基丁氨基)丙氨基博来霉素衍生物及其制备方法。本发明的化合物具有致癌特性，因此可用作药物。
• Synthesis of tri- and tetrapeptide S: the extended C-terminus of bleomycin A2
  作者：Dale L. Boger、Royce F. Menezes

  DOI：10.1021/jo00042a003

  日期：1992.7

  Concise diastereocontrolled syntheses of tri- and tetrapeptide S, key subunits
• Synthesis and biological activity of modified fragments of the antibiotic bleomycin A2
  作者：S. E. Bannikov、G. P. Andronnikova、N. S. Vyrupaeva、E. N. Glibin、Z. V. Pushkareva

  DOI：10.1007/bf00765216

  日期：1983.2