4-azido-3-methylbenzoic acid | 380922-31-6

• 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: 4-azido-3-methylbenzoic acid
• CAS: 380922-31-6
• 化学式: C₈H₇N₃O₂
• 分子量: 177.162
• InChiKey: REARPIJVKCGFNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  51.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-azido-3-methylbenzoic acid 在 4-二甲氨基吡啶 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.33h， 生成 2-(4-azido-3-methylphenyl)-4-acetyl-5-(3,4,5-trimethoxyphenyl)-Δ2,3-oxadiazoline
  参考文献：
  名称：

  New Antimitotic Agents with Activity in Multi-Drug-Resistant Cell Lines and in Vivo Efficacy in Murine Tumor Models

  摘要：

  During a screen for compounds that could inhibit cell proliferation, a series of new tubulin-binding compounds was identified with the discovery of oxadiazoline 1 (A-105972). This compound showed good cytotoxic activity against non-multi-drug-resistant and multi-drug-resistant cancer cell lines, but its utility in vivo was limited by a short half-life. Medicinal chemistry efforts led to the discovery of indolyloxazoline 22g (A-259745), which maintained all of the in vitro activity seen with oxadiazoline 1, but also demonstrated a better pharmacokinetic profile, and dose-dependent in vivo activity. Over a 28 day study, indolyloxazoline 22g increased the life span of tumor-implanted mice by up to a factor of 3 upon oral dosing. This compound, and others of its structural class, may prove to be useful in the development of new chemotherapeutic agents to treat human cancers.

  DOI：

  10.1021/jm010231w
• 作为产物：
  描述：

  4-氨基-3-甲基苯甲酸甲酯 在 硫酸 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 1.92h， 生成 4-azido-3-methylbenzoic acid
  参考文献：
  名称：

  New Antimitotic Agents with Activity in Multi-Drug-Resistant Cell Lines and in Vivo Efficacy in Murine Tumor Models

  摘要：

  During a screen for compounds that could inhibit cell proliferation, a series of new tubulin-binding compounds was identified with the discovery of oxadiazoline 1 (A-105972). This compound showed good cytotoxic activity against non-multi-drug-resistant and multi-drug-resistant cancer cell lines, but its utility in vivo was limited by a short half-life. Medicinal chemistry efforts led to the discovery of indolyloxazoline 22g (A-259745), which maintained all of the in vitro activity seen with oxadiazoline 1, but also demonstrated a better pharmacokinetic profile, and dose-dependent in vivo activity. Over a 28 day study, indolyloxazoline 22g increased the life span of tumor-implanted mice by up to a factor of 3 upon oral dosing. This compound, and others of its structural class, may prove to be useful in the development of new chemotherapeutic agents to treat human cancers.

  DOI：

  10.1021/jm010231w

文献信息

• One-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from nitrobenzenes
  作者：Fen Zhao、Zhen Chen、Kai Xie、Rui Yang、Yu-Bo Jiang

  DOI：10.1016/j.cclet.2015.09.021

  日期：2016.1

  Abstract A facile synthesis of 1,4-disubstituted 1,2,3-triazoles was achieved from nitrobenzenes and terminal alkynes under mild conditions. The reactions were successful for nitrobenzenes and terminal alkynes bearing various functionalities, from which the 1,2,3-triazole derivatives were smoothly synthesized through a four-step one-pot sequence.

  摘要在温和的条件下，由硝基苯和末端炔烃轻松合成了1,4-二取代的1,2,3-三唑。对于具有各种功能的硝基苯和末端炔烃，反应是成功的，通过四步一锅法平稳地合成了1,2,3-三唑衍生物。
• Skeletal Editing of Benzene Motif: Photopromoted Transannulation for Synthesis of DNA-Encoded Seven-Membered Rings
  作者：Yue Zhang、Jia-ying Xue、Xiao-can Su、Wen-jie Xiao、Jing-yi Lv、Wen-xia Shi、Yong Zou、Ming Yan、Xue-jing Zhang

  DOI：10.1021/acs.orglett.4c00377

  日期：2024.3.22

  photopromoted, metal-free transannulation of phenyl azides for the synthesis of DNA-encoded seven-membered rings. The transformation is efficiently achieved through a skeletal editing strategy targeting the benzene motif coupled with a Reversible Adsorption to Solid Support (RASS) strategy. A variety of valuable DNA-encoded seven-membered ring compounds, including DNA-encoded 3H-azepines, azepinones, and

  在本报告中，我们提出了一种光促进、无金属的苯基叠氮化物转环反应，用于合成 DNA 编码的七元环。该转化是通过针对苯基序的骨架编辑策略与可逆吸附到固体支持物（RASS）策略相结合而有效实现的。现在可以获得多种有价值的 DNA 编码的七元环化合物，包括 DNA 编码的 3H-氮杂卓、氮杂酮和非天然氨基酸。至关重要的是，这种与 DNA 兼容的方案也可用于引入复杂分子，例如 Lorcaserin 和 Betahistine。将容易获得的苯环选择性地转化为高价值的七元环，为构建多样化和类药物的 DNA 编码库提供了一条有前途的途径。
• Synthesis and Anticancer Activity of 5-[(1-Aryl-1H-1,2,3-triazol-4-yl)methyl]-10,11-dihydro-5H-dibenzo[b,f]azepines
  作者：K. Sadanandam、P. Pinnoju、M. Sarasija

  DOI：10.1134/s1070428024010184

  日期：2024.1

  novel series of 5-[(1-aryl-1H-1,2,3-triazol-4-yl)methyl]-10,11-dihydro-5H-dibenzo[b,f]azepine derivatives were synthesized by employing click chemistry approach starting from 10,11-dihydro-5H-dibenzo­[b,f]azepine and evaluated for their cytotoxicity against a panel of three cancer cell lines (SiHa, MDA-MB-231, PANC-1). Many of the tested compounds exhibited significant anticancer activity, and compound

  摘要 通过以下方法合成了一系列新型 5-[(1-芳基-1 H -1,2,3-三唑-4-基)甲基]-10,11-二氢-5 H-二苯并[ b , f ]氮杂环庚烷衍生物采用点击化学方法从 10,11-二氢-5 H-二苯并[ b , f ]氮杂卓开始，并评估其对三种癌细胞系（SiHa、MDA-MB-231、PANC-1）的细胞毒性。许多测试的化合物表现出显着的抗癌活性，并且发现化合物4g是该系列中最有前途的类似物。