2-Azido-4-methoxy-benzoyl chloride | 947188-09-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-Azido-4-methoxy-benzoyl chloride
• 英文别名: 2-Azido-4-methoxybenzoyl chloride；2-azido-4-methoxybenzoyl chloride
• CAS: 947188-09-2
• 化学式: C₈H₆ClN₃O₂
• 分子量: 211.608
• InChiKey: XPPHWADFYWGKRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  40.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Azido-4-methoxy-benzoyl chloride 在 吡啶 、 氯化亚砜 作用下， 以 苯 为溶剂， 反应 3.25h， 生成 3-chloro-6-methoxy-2-(4-methoxyphenyl)-2H-indazole
  参考文献：
  名称：

  Indazole Estrogens:  Highly Selective Ligands for the Estrogen Receptor β

  摘要：

  The estrogen receptors, ERalpha and ERbeta, are important pharmaceutical targets. To develop ERbeta-selective ligands, we synthesized a series of nonsteroidal compounds having a phenyl-2H-indazole core with different groups at C-3. Several of these show high affinity and good ERbeta selectivity, especially those with polar and/or polarizable substituents at this site (halogen, CF3, nitrile); the best compounds have affinities for ERbeta comparable to estradiol, with ERbeta affinity selectivity > 100. This potency and ERbeta selectivity is also seen in cell-based transcriptional assays, where several compounds showed ERbeta efficacies equivalent to that of estradiol with ERbeta potency selectivities of 100. These compounds might prove useful as selective pharmacological probes to study the biological actions of estrogens mediated through ERP, and they might lead to the development of useful pharmaceuticals. These findings also contribute to an evolving pharmacophore that characterizes certain nonsteroidal ligands having high ERbeta subtype affinity and potency selectivity.

  DOI：

  10.1021/jm049223g
• 作为产物：
  描述：

  2-azido-4-methoxybenzoic acid 在 光气 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 2-Azido-4-methoxy-benzoyl chloride
  参考文献：
  名称：

  微波辐射辅助串联叠氮还原环化全合成芸香碱及其类似物

  摘要：

  已经通过使用从取代的叠氮基苯甲酸开始的叠氮基还原环化过程开发了芸香果芸香碱和几种类似物的全合成。分子内叠氮基还原环化步骤使用三苯基膦或 Ni 2 B 在 HCl-MeOH (1 M) 中使用微波辐射进行。该合成路线适用于生成喹唑啉酮化合物库。

  DOI：

  10.1055/s-0030-1259095

文献信息

• Identification and initial optimization of inhibitors of Clostridium difficile (C. difficile) toxin B (TcdB)
  作者：Jeffrey J. Letourneau、Ilana L. Stroke、David W. Hilbert、Laurie J. Sturzenbecker、Brett A. Marinelli、Jorge G. Quintero、Joan Sabalski、Linh Ma、David J. Diller、Philip D. Stein、Maria L. Webb

  DOI：10.1016/j.bmcl.2018.01.005

  日期：2018.2

  The discovery, synthesis and preliminary structure-activity relationship (SAR) of a novel class of inhibitors of Clostridium difficile (C. difficile) toxin B (TcdB) is described. A high throughput screening (HTS) campaign resulted in the identification of moderately active screening hits 1–5 the most potent of which was compound 1 (IC50 = 0.77 µM). In silico docking of an early analog offered suggestions

  一类新的抑制剂的发现，合成和初步结构-活性关系（SAR）艰难梭菌（艰难梭菌）毒素B（TcdB的）进行说明。一种高通量筛选（HTS）运动导致中等活性筛选命中的标识1 - 5，其最有效的是化合物1（IC 50  = 0.77微米）。在计算机对接中，早期的类似物为结构修饰提供了建议，从而导致设计和合成了高效的类似物13j（IC 50  = 1 nM）和13 l（IC 50 = 7 nM）作为进一步优化的线索。
• A Silicon Linker for Direct Loading of Aromatic Compounds to Supports. Traceless Synthesis of Pyridine-Based Tricyclics
  作者：Frank X. Woolard、Jonathan Paetsch、Jonathan A. Ellman

  DOI：10.1021/jo9710745

  日期：1997.9.1
• [EN] BENZODIAZEPINE GCNF MODULATORS FOR STEM CELL MODULATION<br/>[FR] MODULATEURS DU GCNF A LA BENZODIAZEPINE DESTINES A MODULER LES CELLULES SOUCHES
  申请人：PHARMACOPEIA INC

  公开号：WO2007095495A2

  公开（公告）日：2007-08-23

  [EN] A genus of benzodiazepines that modulate Germ Cell Nuclear Factor (GCNF) is disclosed. The compounds are useful to regulate stem cell differentiation and as contraceptives. Other embodiments are also disclosed.
  [FR] La présente invention concerne un genre de benzodiazépines qui module le facteur nucléaire de cellules germinales (GCNF). Les composés servent à réguler la différentiation des cellules souches et servent également de contraceptif. L'invention a également trait à d'autres modes de réalisation.
• Indazole Estrogens:  Highly Selective Ligands for the Estrogen Receptor β
  作者：Meri De Angelis、Fabio Stossi、Kathryn A. Carlson、Benita S. Katzenellenbogen、John A. Katzenellenbogen

  DOI：10.1021/jm049223g

  日期：2005.2.1

  The estrogen receptors, ERalpha and ERbeta, are important pharmaceutical targets. To develop ERbeta-selective ligands, we synthesized a series of nonsteroidal compounds having a phenyl-2H-indazole core with different groups at C-3. Several of these show high affinity and good ERbeta selectivity, especially those with polar and/or polarizable substituents at this site (halogen, CF3, nitrile); the best compounds have affinities for ERbeta comparable to estradiol, with ERbeta affinity selectivity > 100. This potency and ERbeta selectivity is also seen in cell-based transcriptional assays, where several compounds showed ERbeta efficacies equivalent to that of estradiol with ERbeta potency selectivities of 100. These compounds might prove useful as selective pharmacological probes to study the biological actions of estrogens mediated through ERP, and they might lead to the development of useful pharmaceuticals. These findings also contribute to an evolving pharmacophore that characterizes certain nonsteroidal ligands having high ERbeta subtype affinity and potency selectivity.
• Total Synthesis of Rutaecarpine and Analogues by Tandem Azido Reductive Cyclization Assisted by Microwave Irradiation
  作者：Ahmed Kamal、Nagula Shankaraiah、M. Reddy、T. Reddy、Leonardo Santos

  DOI：10.1055/s-0030-1259095

  日期：2011.1

  The total synthesis ofrutaecarpine and several analogues has been developed by using an azido reductive cyclization process starting from substituted azido benzoic acids. The intramolecular azido reductive cyclization step was performed with triphenylphosphine or Ni 2 B in HCl―MeOH (1 M) using microwave irradiation. This synthetic route is amenable for the generation of a library of quinazolinone compounds

  已经通过使用从取代的叠氮基苯甲酸开始的叠氮基还原环化过程开发了芸香果芸香碱和几种类似物的全合成。分子内叠氮基还原环化步骤使用三苯基膦或 Ni 2 B 在 HCl-MeOH (1 M) 中使用微波辐射进行。该合成路线适用于生成喹唑啉酮化合物库。