ethyl 2-amino-4-cyclobutylthiophene-3-carboxylate | 1101856-54-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: ethyl 2-amino-4-cyclobutylthiophene-3-carboxylate
• CAS: 1101856-54-5
• 化学式: C₁₁H₁₅NO₂S
• 分子量: 225.312
• InChiKey: UHBZRUBEBNYTFG-UHFFFAOYSA-N

物化性质

• 沸点：
  346.0±42.0 °C(predicted)
• 密度：
  1.242±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  80.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-amino-4-cyclobutylthiophene-3-carboxylate 、 formamide 以70%的产率得到5-cyclobutylthieno[2,3-d]pyrimidin-4(3H)-one
  参考文献：
  名称：

  Identification of the first small-molecule inhibitor of the REV7 DNA repair protein interaction

  摘要：

  DNA interstrand crosslink (ICL) repair (ICLR) has been implicated in the resistance of cancer cells to ICL-inducing chemotherapeutic agents. Despite the clinical significance of ICL-inducing chemotherapy, few studies have focused on developing small-molecule inhibitors for ICLR. The mammalian DNA polymerase zeta, which comprises the catalytic subunit REV3L and the non-catalytic subunit REV7, is essential for ICLR. To identify small-molecule compounds that are mechanistically capable of inhibiting ICLR by targeting REV7, high-throughput screening and structure-activity relationship (SAR) analysis were performed. Compound 1 was identified as an inhibitor of the interaction of REV7 with the REV7-binding sequence of REV3L. Compound 7 (an optimized analog of compound 1) bound directly to REV7 in nuclear magnetic resonance analyses, and inhibited the reactivation of a reporter plasmid containing an ICL in between the promoter and reporter regions. The normalized clonogenic survival of HeLa cells treated with cisplatin and compound 7 was lower than that for cells treated with cisplatin only. These findings indicate that a small-molecule inhibitor of the REV7/REV3L interaction can chemosensitize cells by inhibiting ICLR. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.07.026
• 作为产物：
  描述：

  环丁基甲基酮 、 氰乙酸乙酯 在 吗啉 、 sulfur 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以27%的产率得到ethyl 2-amino-4-cyclobutylthiophene-3-carboxylate
  参考文献：
  名称：

  [EN] NON-FUSED THIOPHENE DERIVATIVES AND THEIR USES
  [FR] DÉRIVÉS DE THIOPHÈNE NON FUSIONNÉS ET LEURS UTILISATIONS

  摘要：

  本发明涉及一类新型非融合噻吩衍生物及其用于治疗感染、癌症、代谢性疾病、心血管疾病、铁贮存紊乱和炎症性疾病等疾病的用途。

  公开号：

  WO2019154953A1

文献信息

• NOVEL COMPOUNDS AS CANNABINOID RECEPTOR LIGANDS
  申请人：Carroll William A.

  公开号：US20090018114A1

  公开（公告）日：2009-01-15

  The present application relates to cannabinoid receptor ligands containing compounds of formula (I) wherein A, R 1 , R 2 , and R 3 are as defined in the specification. The present application also relates to compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions.

  本申请涉及含有式(I)化合物的大麻素受体配体，其中A、R1、R2和R3如规范中所定义。本申请还涉及包含这种化合物的组合物，以及使用这种化合物和组合物治疗疾病和疾病的方法。
• NON-FUSED THIOPHENE DERIVATIVES AND THEIR USES
  申请人：ENYO Pharma

  公开号：EP3749649A1

  公开（公告）日：2020-12-16
• US8338623B2
  申请人：——

  公开号：US8338623B2

  公开（公告）日：2012-12-25
• [EN] NOVEL COMPOUNDS AS CANNABINOID RECEPTOR LIGANDS<br/>[FR] COMPOSÉS NOVATEURS EN TANT QUE LIGANDS DE RÉCEPTEUR DE CANNABINOÏDES
  申请人：ABBOTT LAB

  公开号：WO2009009550A1

  公开（公告）日：2009-01-15

  The present application relates to cannabinoid receptor ligands containing compounds of formula (I) wherein A, R1, R2, and R3 are as defined in the specification. The present application also relates to compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions.