2-azidobenzyl alcohol | 20615-76-3

• 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-azidobenzyl alcohol
• 英文别名: (2-azidophenyl)methanol
• CAS: 20615-76-3
• 化学式: C₇H₇N₃O
• mdl: MFCD24452395
• 分子量: 149.152
• InChiKey: XRMVEVLFARNQHG-UHFFFAOYSA-N

物化性质

• 熔点：
  52-53 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  34.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-azidobenzyl alcohol 在 pyridinium chlorochromate 作用下， 生成 苯甲醯亞胺酸
  参考文献：
  名称：

  量热技术探讨五种邻位取代叠氮苯的热分解

  摘要：

  2-叠氮基苯基甲醇（1），2-叠氮基苯甲醛（2），1-（2-叠氮基苯基）-1-乙酮（3），（2-叠氮基苯基）（苯基）甲酮（4）和1的热分解（TD）通过DSC，TG和C80量热技术在氧化和非氧化条件下分析了-叠氮基-2-硝基苯（5）。众所周知，这些叠氮化物在溶液中的TD可以以高收率得到相应的苯并恶唑，但叠氮化物1除外。当考虑固相和“溶液相” TD反应的结果以及EI-MS实验的结果时，有足够的信息可用来估算叠氮化物的固有分子反应性（MIR）。

  DOI：

  10.1007/s10973-009-0572-8
• 作为产物：
  描述：

  1-叠氮基-2-甲基苯 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 水 作用下， 生成 2-azidobenzyl alcohol
  参考文献：
  名称：

  光化学转化。第二十八部分。芳基叠氮化物作为潜在的光敏保护基

  摘要：

  已经探索了某些芳族叠氮化物作为光敏保护基的潜力。用β-（邻叠氮基苯基）乙醇的烷基或酰基衍生物光解产生吲哚和相应的醇或酸。而ø -azidobenzyl苯甲酸酯光解在质子溶剂，得到的聚合物和小游离酸的衍生物，5-叠氮基-4-羟基甲基-1-甲氧基萘更有效地与受保护基团的释放光解。

  DOI：

  10.1039/j39710000721

文献信息

• Alkyne–azide cycloaddition analogues of dehydrozingerone as potential anti-prostate cancer inhibitors <i>via</i> the PI3K/Akt/NF-kB pathway
  作者：Chetan Kumar、Reyaz Ur Rasool、Zainab Iqra、Yedukondalu Nalli、Prabhu Dutt、Naresh K. Satti、Neha Sharma、Sumit G. Gandhi、Anindya Goswami、Asif Ali

  DOI：10.1039/c7md00267j

  日期：——

  Alkyne–azide cycloaddition derivatives of DHZ (1) were synthesized and screened for cytotoxic potential in which the derivatives, 3, 6, 7, 8, 9 and 15 displayed most potent with IC₅₀ value ranging from 1.8–3.0 μM.

  DHZ（1）的炔基-叠氮环加成衍生物已合成并进行细胞毒性潜力筛选，其中衍生物3、6、7、8、9和15显示出最强的细胞毒性，IC50值范围为1.8-3.0μM。
• 8-Triazolylxanthine derivatives, processes for their production and their use as adenosine receptor antagonists
  申请人：Life & Brain GmbH

  公开号：EP2465859A1

  公开（公告）日：2012-06-20

  The invention relates to derivatives of the general formulae I and II to processes for the production thereof, to pharmaceutical preparations containing said compounds and/or physiologically compatible salts, or solvates which can be produced therefrom as well as to the pharmaceutical use of said compounds, the salts, or solvates thereof as adenosine receptor antagonists, in particular for the treatment of neurodegenerative disorders, e.g. stroke, amylotrophic lateral sclerosis, dementia, Alzheimer's disease, Parkinson's disease, ischemia/reperfusion injury, inflammation, and/or neurological disorder. The blockade of adenosine receptors could also be useful for other indications regarding the metabolism, e.g. diabetic retinopathy, diabetes mellitus, hyperbaric oxygen-induced retinopathy and/or obesity. Applications could also be the treatment of allergic diseases and autoimmune diseases, including mast cell degranulation, asthma, bronchoconstriction, pulmonary fibrosis, inflammatory or obstructive airways disease and/or chronic obstructive pulmonary disease (COPD). In addition, they could be used to treat cancer, e.g. proliferating tumor, cell proliferation disorders, angiogenesis, lung cancer, breast cancer, pancreatic cancer, thyroid cancer, skin cancer, vascular endothelial cancer, cancer of the central nervous system, esophageal cancer, cancer of the larynx, gastrointestinal cancer, colon cancer, colorectal cancer, rectal cancer, liver cancer, renal cancer, prostate cancer, bladder cancer, cervical cancer, ovarian cancer, endometrial cancer, melanoma, squamous cell carcinoma, basal cell carcinoma, non-small cell lung cancer selected from squamous cell carcinoma, adenocarcinoma, large cell carcinoma, adenosquam- ous carcinoma and/or undifferentiated carcinoma. The diseases associated with adenosine receptors are also diabetes, diarrhea, inflammatory bowel disease and/or gastrointestinal tract disorders. Adenosine receptor antagonists could be effective for treating a hepatic disease or condition for reducing fat deposition in the liver or fibrosis of the liver. The use of compounds of general formulae I and II can be associated with many applications e.g., scleroderm arthritis, atherosclerosis, urticaria, myocardial infarction, myocardial reperfusion after ischemia, vasodilation, hypertension, hypersensitivity, myocardial ischemia, heart attack and/or retinopathy of prematurity.

  本发明涉及具有通用公式I和II的衍生物，以及它们的制备方法，包含所述化合物的药物制剂以及/或可以从它们产生的生理上相容的盐或溶剂化物，以及所述化合物、盐或溶剂化物作为腺苷受体拮抗剂的药物用途，特别是用于治疗神经退行性疾病，例如中风、肌萎缩侧索硬化、痴呆、阿尔茨海默病、帕金森病、缺血/再灌注损伤、炎症和/或神经系统疾病。腺苷受体的阻断还可能对其他与代谢有关的适应症有益，例如糖尿病视网膜病变、糖尿病、高氧引起的视网膜病变和/或肥胖。应用还可能是治疗过敏性疾病和自身免疫性疾病，包括肥大细胞脱粒、哮喘、支气管收缩、肺纤维化、炎症性或阻塞性气道疾病和/或慢性阻塞性肺病（COPD）。此外，它们还可用于治疗癌症，例如增殖性肿瘤、细胞增殖障碍、血管生成、肺癌、乳腺癌、胰腺癌、甲状腺癌、皮肤癌、血管内皮癌、中枢神经系统癌症、食管癌、喉癌、胃肠癌、结肠癌、结直肠癌、直肠癌、肝癌、肾癌、前列腺癌、膀胱癌、宫颈癌、卵巢癌、子宫内膜癌、黑色素瘤、鳞状细胞癌、基底细胞癌、非小细胞肺癌（包括鳞状细胞癌、腺癌、大细胞癌、腺鳞癌和/或未分化癌）。与腺苷受体相关的疾病还包括糖尿病、腹泻、炎症性肠病和/或胃肠道的疾病。腺苷受体拮抗剂可能对治疗肝脏疾病或状况有效，用于减少肝脏脂肪沉积或肝脏纤维化。通用公式I和II的化合物的使用可以与许多应用相关，例如，硬皮病关节炎、动脉粥样硬化、荨麻疹、心肌梗死、缺血后心肌再灌注、血管扩张、高血压、过敏反应、心肌缺血、心脏病发作和/或早产儿视网膜病变。
• A Method for the Synthesis of Substituted Quinolines via Electrophilic Cyclization of 1-Azido-2-(2-propynyl)benzene
  作者：Zhibao Huo、Ilya D. Gridnev、Yoshinori Yamamoto

  DOI：10.1021/jo902603v

  日期：2010.2.19

  A new and efficient strategy for the synthesis of substituted quinolines via electrophilic cyclization is developed. The intramolecular cyclization of 1-azido-2-(2-propynyl)benzene 1 proceeds smoothly in the presence of electrophilic reagents (I2, Br2, ICl, NBS, NIS, and HNTf2) in CH3NO2 at room temperature or in the presence of catalytic amounts of AuCl3/AgNTf2 in THF at 100 °C to afford the corresponding

  开发了一种通过亲电环化合成取代喹啉的新的有效策略。在室温下，在CH 3 NO 2中存在亲电试剂（I 2，Br 2，ICl，NBS，NIS和HNTf 2）的情况下，1-叠氮基-2-（2-丙炔基）苯1的分子内环化过程顺利进行。或在100°C的THF中催化量的AuCl 3 / AgNTf 2的存在下，以高至高收率得到相应的喹啉2。对于亲电子试剂，根据试剂类型，E等于2可以是I，Br或H，而E等于2 在亲电催化剂的情况下，H为H。
• [EN] 8-TRIAZOLYLXANTHINE DERIVATIVES, PROCESSES FOR THEIR PRODUCTION AND THEIR USE AS ADENOSINE RECEPTOR ANTAGONISTS<br/>[FR] DÉRIVÉS DE 8-TRIAZOLYLXANTHINE, LEURS PROCÉDÉS DE FABRICATION ET LEUR UTILISATION EN TANT QU'AGONISTES DE RÉCEPTEURS DE L'ADÉNOSINE
  申请人：LIFE & BRAIN GMBH

  公开号：WO2012076974A1

  公开（公告）日：2012-06-14

  The invention relates to derivatives of the general formulae (I) and (II) to processes for the production thereof, to pharmaceutical preparations containing said compounds and/or physiologically compatible salts or solvates or prodrugs which can be produced therefrom as well as to the pharmaceutical use of said compounds, the salts or solvates thereof as adenosine receptor antagonists, in particular for the treatment of neurodegenerative disorders, e.g. stroke, amylotrophic lateral sclerosis, dementia, Alzheimer's disease, Parkinson's disease, ischemia/reperfusion injury, inflammation, and/or neurological disorder. The blockade of adenosine receptors could also be useful for other indications regarding the metabolism, e.g. diabetic retinopathy, diabetes mellitus, hyperbaric oxygen - induced retinopathy and/or obesity. Applications could also be the treatment of allergic diseases and autoimmune diseases, including mast cell degranulation, asthma, bronchoconstriction, pulmonary fibrosis, inflammatory or obstructive airways disease and/or chronic obstructive pulmonary disease (COPD). In addition, they could be used to treat cancer. The diseases associated with adenosine receptors are also diabetes, diarrhea, inflammatory bowel disease and/or gastrointestinal tract disorders. Adenosine receptor antagonists could be effective for treating a hepatic disease or condition for reducing fat deposition in the liver or fibrosis of the liver. The use of compounds of general formulae I or II can be associated with many applications e.g., scleroderm arthritis, atherosclerosis, urticaria, myocardial infarction, myocardial reperfusion after ischemia, vasodilation, hypertension, hypersensitivity, myocardial ischemia, heart attack and/or retinopathy of prematurity.

  本发明涉及具有通用公式(I)和(II)的衍生物，以及它们的制备方法，含有所述化合物的药物制剂以及/或可以从它们产生的生理上相容的盐或溶剂化物或前药，以及所述化合物、其盐或溶剂化物作为腺苷受体拮抗剂的药物用途，特别是用于治疗神经退行性疾病，例如中风、肌萎缩性侧索硬化症、痴呆、阿尔茨海默病、帕金森病、缺血/再灌注损伤、炎症和/或神经系统疾病。阻断腺苷受体对于涉及代谢的其他适应症也可能有用，例如糖尿病视网膜病变、糖尿病、高氧诱导视网膜病变和/或肥胖。应用还可以包括治疗过敏性疾病和自身免疫性疾病，包括肥大细胞脱粒、哮喘、支气管收缩、肺纤维化、炎症性或阻塞性气道疾病和/或慢性阻塞性肺病（COPD）。此外，它们还可以用于治疗癌症。与腺苷受体相关的疾病还包括糖尿病、腹泻、炎症性肠病和/或胃肠道疾病。腺苷受体拮抗剂可能对治疗肝病或减少肝脏脂肪沉积或肝脏纤维化有效。通用公式I或II的化合物的使用可以与许多应用相关联，例如，硬皮病关节炎、动脉硬化、荨麻疹、心肌梗死、缺血后心肌再灌注、血管舒张、高血压、过敏反应、心肌缺血、心脏病发作和/或早产儿视网膜病变。
• Leucine ureido derivatives as aminopeptidase N inhibitors using click chemistry. Part II
  作者：Jiangying Cao、Jie Zang、Xiujie Kong、Chunlong Zhao、Ting Chen、Yingying Ran、Hang Dong、Wenfang Xu、Yingjie Zhang

  DOI：10.1016/j.bmc.2019.01.041

  日期：2019.3

  biological evaluation and structure-activity relationship of one new series of leucine ureido derivatives containing the 1,2,3-triazole moiety. Among them, compound 31f was identified as the best APN inhibitor with IC50 value being two orders of magnitude lower than that of the positive control bestatin. Compound 31f possessed selective cytotoxicity to several tumor cell lines over the normal cell line

  氨基肽酶N（APN）已被证明与癌症血管生成，转移和侵袭密切相关。因此，APN作为有希望的抗肿瘤靶标越来越受到关注。在当前的研究中，我们报告了一个新的系列的包含1,2,3-三唑部分的亮氨酸脲基衍生物的设计，合成，生物学评估和结构-活性关系。其中，化合物31f被确定为最佳的APN抑制剂，IC50值比阳性对照的Bestatin低两个数量级。相对于正常细胞系人脐静脉内皮细胞（HUVEC），化合物31f对几种肿瘤细胞系具有选择性的细胞毒性。值得注意的是，当与5-氟尿嘧啶（5-Fu）结合使用时，31f对几种肿瘤细胞系表现出协同的抗增殖作用。在相同的浓度下，在HUVECs毛细管形成试验和大鼠胸主动脉环试验中，31f的抗血管生成活性比Bestatin更好。在体外抗侵袭试验中，31f还显示出比Bestatin更高的效价。此外，在小鼠肝癌H22肿瘤移植模型中，观察到相当大的31f单独或与5-Fu联合使用的体内抗肿瘤效力，而没有明显的毒性迹象。