methyl 2-azido-5-iodobenzoate | 185505-58-2

• 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: methyl 2-azido-5-iodobenzoate
• 英文别名: 2-Azido-5-iodo-benzoic acid methyl ester
• CAS: 185505-58-2
• 化学式: C₈H₆IN₃O₂
• 分子量: 303.059
• InChiKey: QAAWZVVPVQTCBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 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：

  methyl 2-azido-5-iodobenzoate 在 copper(l) iodide 、 TTTA 、 水 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 25.0h， 生成 N-[4-iodo-2-(pyrrolidin-1-ylcarbonyl)phenyl]-2-[(5-methyl-1,3,4-oxadiazol-2-yl)thio]hexanamide
  参考文献：
  名称：

  2-(5-Iodo-1,2,3-triazolyl)苯甲酸的环化触发脱氮转化

  摘要：

  发现了 [1,2,3] 三唑并苯并恶嗪酮作为“隐藏”重氮基团来源的能力。这些重氮前体可以很容易地通过 2-(5-iodo-1,2,3-triazolyl) 苯甲酸的分子内环化来制备。隐藏的重氮基团的 Cu 催化捕获允许通过脱氮途径进行进一步的功能化。转化通过形成重氮亚胺或重氮酰胺中间体进行。使用一锅环化/重氮捕获程序开发了各种邻氨基苯甲酰胺以及硫醇化苯并恶嗪酮的新途径。

  DOI：

  10.1021/acs.joc.2c00235
• 作为产物：
  描述：

  2-氨基-5-碘苯甲酸 在 氯化亚砜 、 sodium nitrite 作用下， 反应 1.0h， 生成 methyl 2-azido-5-iodobenzoate
  参考文献：
  名称：

  2-(5-Iodo-1,2,3-triazolyl)苯甲酸的环化触发脱氮转化

  摘要：

  发现了 [1,2,3] 三唑并苯并恶嗪酮作为“隐藏”重氮基团来源的能力。这些重氮前体可以很容易地通过 2-(5-iodo-1,2,3-triazolyl) 苯甲酸的分子内环化来制备。隐藏的重氮基团的 Cu 催化捕获允许通过脱氮途径进行进一步的功能化。转化通过形成重氮亚胺或重氮酰胺中间体进行。使用一锅环化/重氮捕获程序开发了各种邻氨基苯甲酰胺以及硫醇化苯并恶嗪酮的新途径。

  DOI：

  10.1021/acs.joc.2c00235

文献信息

• FACTOR Xa INHIBITORS
  申请人：Jia Zhaozhong J.

  公开号：US20080293704A1

  公开（公告）日：2008-11-27

  The present invention is directed to compounds represented by Formula (I) or a pharmaceutically acceptable salt, ester, or prodrug thereof which are inhibitors of Factor Xa. The present invention is also directed to intermediates used in making such compounds, pharmaceutical compositions containing such compounds, methods to prevent or treat certain conditions characterized by undesired thrombosis and methods of inhibiting the coagulation of a blood sample.

  本发明涉及由公式（I）表示的化合物或其药学上可接受的盐、酯或前药，其为Xa因子的抑制剂。本发明还涉及用于制备这种化合物的中间体，包含这种化合物的制药组合物，预防或治疗某些由不希望的血栓形成所表现出的病症的方法，以及抑制血样的凝血作用的方法。
• FACTOR XA INHIBITORS
  申请人：Jia Zhaozhong J.

  公开号：US20110160196A1

  公开（公告）日：2011-06-30

  The present invention is directed to compounds represented by Formula (I) or a pharmaceutically acceptable salt, ester, or prodrug thereof which are inhibitors of Factor Xa. The present invention is also directed to intermediates used in making such compounds, pharmaceutical compositions containing such compounds, methods to prevent or treat certain conditions characterized by undesired thrombosis and methods of inhibiting the coagulation of a blood sample.

  本发明涉及由式(I)表示的化合物或其药学上可接受的盐、酯或前药，其为因子Xa的抑制剂。本发明还涉及用于制备这种化合物的中间体，含有这种化合物的药物组合物，预防或治疗由不良血栓形成所表征的某些疾病的方法，以及抑制血液样品凝血的方法。
• [EN] FACTOR XA INHIBITORS<br/>[FR] INHIBITEURS DU FACTEUR XA
  申请人：MILLENNIUM PHARM INC

  公开号：WO2008086226A8

  公开（公告）日：2009-10-15
• A photoaffinity probe for 5-hydroxyeicosanoid dehydrogenase suitable for radioiodination
  作者：Seongjin Kim、Yurdanur Adiyaman、Goutam Saha、William S Powell、Joshua Rokach

  DOI：10.1016/s0040-4039(01)00699-2

  日期：2001.7

  5-Hydroxy eicosanoid dehydrogenase (5h-dh) is a key enzyme responsible for the biosynthesis of 5-oxo-ETE, a potent eosinophil chemoattractant. To facilitate the identification and characterization of jh-dh we have synthesized a photoaffinity ligand 7, designed to bind to the enzyme, and shown it to be an excellent substrate for Sh-dh. We have also synthesized a precursor 34, containing the photoaffinity label and a trimethyl tin group that can readily be displaced by iodide and will be suitable for radioiodination with I-125. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Simplified Cyclic Analogues of Bastadin-5. Structure−Activity Relationships for Modulation of the RyR1/FKBP12 Ca²⁺ Channel Complex
  作者：Makoto N. Masuno、Isaac N. Pessah、Marilyn M. Olmstead、Tadeusz F. Molinski

  DOI：10.1021/jm050708u

  日期：2006.7.1

  Bastadin-5, a brominated macro-dilactam from the marine sponge Ianthella basta, enhances release of Ca2+ from stores within the sarcoplasmic reticulum (SR) of muscle and nonmuscle cells by modulating RyR1/FKBP12 complex. Analogues of bastadin-5 present desirable targets for SAR studies to shed light on the gating mechanism and locus of bastadin-5 binding on these heteromeric channels that mediate essential steps in early coupling of membrane excitation to Ca2+ signaling cascades. Simple, ring-constrained analogues of bastadin-5 were synthesized from substituted benzaldehydes in a convergent manner, featuring an efficient SNAr macroetherification, and evaluated in an assay that measures [H-3]-ryanodine that is known to correlate with the functional open state of the Ca2+ channel. The simplified 14-membered ring, atropisomeric analogue (+/-)-7, like bastadin-5, enhanced ryanodine binding to the RyR1/FKBP12 complex (EC50 11 mu M), however, unexpectedly, the corresponding achiral 18-membered ring analogue 14 potently inhibited binding (IC50 6 mu M) under the same conditions. Structure-activity relationships of both families of cyclic analogues showed activity in a ryanodine binding assay that varied with substitutions of the Br atom on the trisubstituted aryl ring by various functional groups. The most active analogues were those that conserved the dibromocatechol ether moiety that corresponds to the 'western edge' of the bastadin-5 structure. These data suggest that cyclic analogues of bastadin-5 interact with the channel complex in a complex manner that can either enhance or inhibit channel activity.