ethyl bromoacetate | 872213-29-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: ethyl bromoacetate
• 英文别名: ethyl 2-(9H-carbazol-2-yloxy)acetate
• CAS: 872213-29-1
• 化学式: C₁₆H₁₅NO₃
• 分子量: 269.3
• InChiKey: MWJGJQXYOYNBFQ-UHFFFAOYSA-N

物化性质

• 沸点：
  458.1±20.0 °C(Predicted)
• 密度：
  1.264±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  51.32
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl bromoacetate 在 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 3.25h， 生成 2-(9H-carbazol-4-yloxy)-N-[2-(2-methoxyphenoxy)ethyl]acetamide
  参考文献：
  名称：

  Novel Carvedilol Analogues That Suppress Store-Overload-Induced Ca²⁺ Release

  摘要：

  Carvedilol is a uniquely effective drug for the treatment of cardiac arrhythmias in patients with heart failure. This activity is in part because of its ability to inhibit store-overload-induced calcium release (SOICR) through the RyR2 channel. We describe the synthesis, characterization, and bioassay of ca. 100 compounds based on the carvedilol motif to identify features that correlate with and optimize SOICR inhibition. A single-cell bioassay was employed on the basis of the RyR2-R4496C mutant HEK-293 cell line in which calcium release from the endoplasmic reticulum through the defective channel was measured. IC50 values for SOICR inhibition were thus obtained. The compounds investigated contained modifications to the three principal subunits of carvedilol, including the carbazole and catechol moieties, as well as the linker chain containing the beta-amino alcohol functionality. The SAR results indicate that significant alterations are tolerated in each of the three subunits.

  DOI：

  10.1021/jm401090a
• 作为产物：
  描述：

  4-羟基咔唑 、 溴乙酸乙酯 在 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 ethyl bromoacetate
  参考文献：
  名称：

  Novel Carvedilol Analogues That Suppress Store-Overload-Induced Ca²⁺ Release

  摘要：

  Carvedilol is a uniquely effective drug for the treatment of cardiac arrhythmias in patients with heart failure. This activity is in part because of its ability to inhibit store-overload-induced calcium release (SOICR) through the RyR2 channel. We describe the synthesis, characterization, and bioassay of ca. 100 compounds based on the carvedilol motif to identify features that correlate with and optimize SOICR inhibition. A single-cell bioassay was employed on the basis of the RyR2-R4496C mutant HEK-293 cell line in which calcium release from the endoplasmic reticulum through the defective channel was measured. IC50 values for SOICR inhibition were thus obtained. The compounds investigated contained modifications to the three principal subunits of carvedilol, including the carbazole and catechol moieties, as well as the linker chain containing the beta-amino alcohol functionality. The SAR results indicate that significant alterations are tolerated in each of the three subunits.

  DOI：

  10.1021/jm401090a

文献信息

• [EN] NOVEL CARBAZOLE DERIVATIVE AND PHARMACEUTICAL COMPOSITION FOR PREVENTION OR TREATMENT OF CANCER COMPRISING SAME AS ACTIVE INGREDIENT<br/>[FR] NOUVEAU DÉRIVÉ DE CARBAZOLE ET COMPOSITION PHARMACEUTIQUE POUR LA PRÉVENTION OU LE TRAITEMENT DU CANCER LE COMPRENANT EN TANT QUE PRINCIPE ACTIF<br/>[KO] 신규한 카바졸 유도체 및 이를 유효성분으로 포함하는 암의 예방 또는 치료용 약학적 조성물
  申请人：[en]CURACLE CO., LTD.;[ko]주식회사 큐라클

  公开号：WO2022103149A1

  公开（公告）日：2022-05-19

  본 발명은 신규한 카바졸 유도체 화합물, 이의 입체 이성질체, 이의 수화물, 또는 이의 약학적으로 허용 가능한 염, 및 이를 유효성분으로 함유하는 암의 예방 또는 치료를 위한 약학적 조성물에 관한 것으로, 본 발명에서 제공하는 상기 신규한 카바졸 유도체는 과도한 활성으로 세포의 지속적 성장과 분열을 유도해 암을 유발하는 AKT 인산화를 우수하게 억제할 수 있는 효과가 있어 암의 예방 또는 치료에 유용하게 사용될 수 있다.
• KR2022/63753
  申请人：——

  公开号：——

  公开（公告）日：——
• Novel Carvedilol Analogues That Suppress Store-Overload-Induced Ca²⁺ Release
  作者：Chris D. Smith、Aixia Wang、Kannan Vembaiyan、Jingqun Zhang、Cuihong Xie、Qiang Zhou、Guogen Wu、S. R. Wayne Chen、Thomas G. Back

  DOI：10.1021/jm401090a

  日期：2013.11.14

  Carvedilol is a uniquely effective drug for the treatment of cardiac arrhythmias in patients with heart failure. This activity is in part because of its ability to inhibit store-overload-induced calcium release (SOICR) through the RyR2 channel. We describe the synthesis, characterization, and bioassay of ca. 100 compounds based on the carvedilol motif to identify features that correlate with and optimize SOICR inhibition. A single-cell bioassay was employed on the basis of the RyR2-R4496C mutant HEK-293 cell line in which calcium release from the endoplasmic reticulum through the defective channel was measured. IC50 values for SOICR inhibition were thus obtained. The compounds investigated contained modifications to the three principal subunits of carvedilol, including the carbazole and catechol moieties, as well as the linker chain containing the beta-amino alcohol functionality. The SAR results indicate that significant alterations are tolerated in each of the three subunits.