1-azido-7-aminoheptane | 867338-62-3

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 1-azido-7-aminoheptane
• 英文别名: 7-azido-1-aminoheptane；7-azidoheptan-1-amine；7-azido-1-heptanamine
• CAS: 867338-62-3
• 化学式: C₇H₁₆N₄
• 分子量: 156.231
• InChiKey: VTHWVKRZWJBOTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-azido-7-aminoheptane 在 N-甲基吗啉 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 (2S,4R)-1-[(2S)-3,3-dimethyl-2-(6-{1-[7-({2-methyl-8-[4-(trifluoromethyl)phenyl]-2H,8H-pyrazolo[3,4-b]indol-5-yl}formamido)heptyl]-1H-1,2,3-triazol-4-yl}hexanamido)butanoyl]-4-hydroxy-N-{[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl}pyrrolidine-2-carboxamide
  参考文献：
  名称：

  [EN] HETEROBIFUNCTIONAL MOLECULES AS TEAD INHIBITORS
  [FR] MOLÉCULES HÉTÉROBIFONCTIONNELS UTILISÉES EN TANT QU'INHIBITEURS DE TEAD

  摘要：

  Compounds of the formula (I) Q1-Q2-Q3(I) in which Q1, Q2and Q3have the meanings indicated in Claim 1, degrade target proteins, and can be employed, inter alia, for the treatment of diseases and conditions mediated by such target proteins.

  公开号：

  WO2023078813A1
• 作为产物：
  描述：

  1,7-二溴庚烷 在 盐酸 、 sodium azide 、 三苯基膦 作用下， 以 乙醚 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 1-azido-7-aminoheptane
  参考文献：
  名称：

  具有氟化硅受体的4- N-酰基和4- N-烷基吉西他滨类似物：在18 F-放射性标记中的应用

  摘要：

  使用肽偶联条件将吉西他滨与官能化的羧酸偶联，得到具有末端炔或叠氮基部分的4- N-烷酰基类似物。4- N-甲苯磺酰基吉西他滨与叠氮基烷基胺的反应提供了具有末端叠氮基的4- N-烷基吉西他滨。点击用，得到硅烷积木反应4- ñ -烷酰基或4- ñ -烷基吉西他滨的类似物适合于氟化。RP-HPLC分析表明4- N-烷基吉西他滨类似物在酸性水溶液条件下比4- N-烷酰基类似物更好的化学稳定性。4- N-烷酰基吉西他滨类似物显示出对L1210细胞系有效的细胞抑制活性，但4- N-烷基吉西他滨类似物的细胞毒性较低。然而，4- N-烷酰基和4- N-烷基类似物在HEK293细胞中具有相当的抗增殖活性。用Fluor 488-炔烃标记后，通过荧光显微镜观察，带有叠氮末端基团的4- N-烷基类似物位于HEK293细胞内。[ 18 F] 4 -N-烷基或烷酰基硅烷吉西他滨类似物已成功使用微型和常规的硅烷标记放射

  DOI：

  10.1016/j.ejmech.2018.02.017

文献信息

• Synthesis and biological evaluation of hybrid acridine-HSP90 ligand conjugates as telomerase inhibitors
  作者：S. Roe、M. Gunaratnam、C. Spiteri、P. Sharma、R. D. Alharthy、S. Neidle、J. E. Moses

  DOI：10.1039/c5ob01177a

  日期：——

  The synthesis and biological evaluation of a series of bifunctional acridine-HSP90 inhibitor ligands as telomerase inhibitors is herein described.

  本文介绍了一系列双功能的吖啶-HSP90抑制剂配体的合成和生物评价，作为端粒酶抑制剂。
• Developing selective PI3K degraders to modulate both kinase and non-kinase functions
  作者：Zimo Yang、Yan Tong、Yongbo Liu、Qianlong Liu、Zhihao Ni、Yuna He、Yu Rao

  DOI：10.1016/j.cclet.2024.109577

  日期：2024.11

  achieve the isoform-selective degradation of class I phosphoinositide 3-kinases (PI3Ks) in this study. Through screening and optimization, the PROTAC molecule was identified as a selective degrader of p110 in multiple breast cancer cells. More importantly, the degrader can down-regulate p85 regulatory subunit simultaneously, thereby inhibiting the non-enzymatic functions of PI3K that are independent on p110

  本研究首次利用蛋白水解靶向嵌合体（PROTAC）技术实现I类磷酸肌醇3激酶（PI3K）的异构体选择性降解。通过筛选和优化，PROTAC分子被鉴定为多种乳腺癌细胞中p110的选择性降解剂。更重要的是，降解剂可以同时下调p85调节亚基，从而抑制PI3K独立于p110催化亚基的非酶功能。因此，与PI3K抑制剂copanlisib相比，对乳腺癌细胞表现出更强的抗增殖活性。简而言之，我们开发了一种选择性且高效的 PROTAC 分子来诱导 p110 降解并同时减少 p85 蛋白，通过阻断 PI3K- 的酶促和非酶促功能，为 PI3K- 的生物学研究提供工具化合物。
• Structure−Activity Relationship for Thiohydantoin Androgen Receptor Antagonists for Castration-Resistant Prostate Cancer (CRPC)
  作者：Michael E. Jung、Samedy Ouk、Dongwon Yoo、Charles L. Sawyers、Charlie Chen、Chris Tran、John Wongvipat

  DOI：10.1021/jm901488g

  日期：2010.4.8

  A structure activity relationship study was carried out on a series of thiohydantoins and their analogues 14 which led to the discovery of 92 (MDV3100) as the clinical candidate for the treatment of hormone refractory prostate cancer.
• Degradation versus Inhibition: Development of Proteolysis-Targeting Chimeras for Overcoming Statin-Induced Compensatory Upregulation of 3-Hydroxy-3-methylglutaryl Coenzyme A Reductase
  作者：Mei-Xin Li、Yiqing Yang、Qiuye Zhao、Yue Wu、Lei Song、Haiyan Yang、Ming He、Hongying Gao、Bao-Liang Song、Jie Luo、Yu Rao

  DOI：10.1021/acs.jmedchem.0c00339

  日期：2020.5.14

  3-Hydroxy-3-methylglutaryl coenzyme A reductase (HMGCR) is an eight-pass transmembrane protein in the endoplasmic reticulum (ER) and a classical drug target to treat dyslipidemia. Statins including the well-known atorvastatin (Lipitor; Pfizer) have been widely used for the prevention and treatment of cardiovascular disease for decades. However, statins can elicit a compensatory upregulation of HMGCR protein and cause adverse effects including skeletal muscle damage. They are ineffective for patients with statin intolerance. Inspired by the recently emerging proteolysis-targeting chimeras (PROTACs), we set out to eliminate HMGCR protein using PROTAC-mediated degradation. One PROTAC designated as P22A was found to reduce HMGCR protein level and block cholesterol biosynthesis potently with less compensatory upregulation of HMGCR. To the best of our knowledge, HMGCR is the first ER-localized, polytopic transmembrane protein successfully degraded by the PROTAC technique. This finding may provide a new strategy to lower cholesterol levels and treat the associated diseases.
• Retinoic acid and evernyl-based menadione-triazole hybrid cooperate to induce differentiation of neuroblastoma cells
  作者：Jolly Janette Mendonza、Srilakshmi Tirupathamma Reddy、Hashnu Dutta、Venkata Krishna Kanth Makani、Venkata Mallavadhani Uppuluri、Nishant Jain、Manika Pal Bhadra

  DOI：10.1007/s00210-023-02489-3

  日期：2023.10