{2-[(2,6-Bis-hydroxymethyl-4-methyl-phenoxycarbonyl)-methyl-amino]-ethyl}-methyl-carbamic acid tert-butyl ester | 633314-24-6

• 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: {2-[(2,6-Bis-hydroxymethyl-4-methyl-phenoxycarbonyl)-methyl-amino]-ethyl}-methyl-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[2-[[2,6-bis(hydroxymethyl)-4-methylphenoxy]carbonyl-methylamino]ethyl]-N-methylcarbamate
• CAS: 633314-24-6
• 化学式: C₁₉H₃₀N₂O₆
• 分子量: 382.457
• InChiKey: MFEFVWUNPFAAQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  99.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  {2-[(2,6-Bis-hydroxymethyl-4-methyl-phenoxycarbonyl)-methyl-amino]-ethyl}-methyl-carbamic acid tert-butyl ester 在 三乙胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 [2-({4-[({2-[(2,6-Bis-hydroxymethyl-4-methyl-phenoxycarbonyl)-methyl-amino]-ethyl}-methyl-carbamoyloxy)-methyl]-2,6-dimethoxy-phenoxycarbonyl}-methyl-amino)-ethyl]-methyl-carbamic acid 3-hydroxy-3-methyl-5-oxo-hexyl ester
  参考文献：
  名称：

  催化抗体 38C2 对自焚树突前药的生物活化

  摘要：

  自焚树枝状大分子最近被开发并引入作为多前药的潜在平台。这些独特的结构树枝状大分子可以通过自毁链断裂释放所有尾部单元，这是由树枝状大分子核心的单个切割引发的。药物分子作为尾部单元和酶底物作为触发器的结合可以产生多前药单元，该单元将被单个酶促裂解激活。我们已经合成了第一代以阿霉素和喜树碱为尾部单元的树突状前药，以及一个可被催化抗体 38C2 切割的反醇醛醇反迈克尔焦灶触发器。在存在和不存在抗体 38C2 的情况下，使用 Molt-3 白血病细胞系在细胞生长抑制试验中评估树突前药的生物活性。树突单元被用作异二聚体前药的平台，通过其生物活化实现了毒性的显着增加。

  DOI：

  10.1021/ja039052p
• 作为产物：
  描述：

  (2-{[2,6-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-phenoxycarbonyl]-methyl-amino}-ethyl)-methyl-carbamic acid tert-butyl ester 在 Amberlyst-15 作用下， 以 甲醇 为溶剂， 以78 %的产率得到{2-[(2,6-Bis-hydroxymethyl-4-methyl-phenoxycarbonyl)-methyl-amino]-ethyl}-methyl-carbamic acid tert-butyl ester
  参考文献：
  名称：

  自焚树突水凝胶

  摘要：

  智能水凝胶在药物输送和传感等领域备受关注。由于其结构精度，基于树枝状聚合物的水凝胶可以表现出可调的特性。我们从自焚树突中制备了水凝胶。展示了响应光的受控水凝胶降解，并比较了作为树突生成函数的水凝胶特性。

  DOI：

  10.1039/d1cc05108c

文献信息

• 一种具有肿瘤微环境响应的二聚体前药以及一种光调控纳米药物及应用
  申请人：苏州大学

  公开号：CN109134516B

  公开（公告）日：2022-02-11

  本发明提供了一种光调控纳米药物，以式Ⅰ所示的具有肿瘤微环境响应的二聚体前药，两亲性高分子材料和共载药物，通过自组装形成纳米粒。形成的核壳结构纳米药物具有超高载药量和良好的稳定性。在光照的条件下，能够特异性的释放药物，实现协同抗肿瘤治疗。
• 유전자 비독성 항암 치료를 위한 항생제 변형 항암제 화합물 및 이를 포함하는 항암 약학 조성물
  申请人：Korea University Research and Business Foundation 고려대학교 산학협력단(220040170680) BRN ▼209-82-08298

  公开号：KR20210093601A

  公开（公告）日：2021-07-28

  본 발명은 유전자 비독성 항암 치료를 위한 항생제 변형 항암제 화합물 및 이를 포함하는 항암 약학 조성물에 관한 것으로서, 본 발명에 따른 변형 항생제 항암 약물은 암세포의 미토콘드리아만을 표적하는 방식으로 치료 효과를 내기 때문에 핵 DNA를 손상시켜 암세포를 사멸시키는 기존의 화학요법과는 달리 유전자 변성을 일으키지 않아 암의 재발을 예방할 수 있으며, 또한 본 발명에 따른 화합물을 이용한 미토콘드리아 표적 치료법은 일반적인 항암 치료에 의해 약물 저항성을 획득해 치료가 어려운 악성 종양을 효과적으로 치료할 수 있다.

  本发明涉及一种用于基因非毒性抗癌治疗的抗生素改良抗癌化合物以及包含该化合物的抗癌药物组合物，根据本发明，改良抗生素抗癌药物通过定位癌细胞的线粒体来产生治疗效果，与传统的化学疗法通过损害细胞核DNA以消灭癌细胞的方式不同，不会引起基因突变，从而可以预防癌症的复发。此外，利用本发明的化合物进行线粒体定位治疗法可以有效治疗因常规抗癌治疗导致药物耐药性而难以治疗的恶性肿瘤。
• Mitochondrial Relocation of a Common Synthetic Antibiotic: A Non-genotoxic Approach to Cancer Therapy
  作者：Kyoung Sunwoo、Miae Won、Kyung-Phil Ko、Miri Choi、Jonathan F. Arambula、Sung-Gil Chi、Jonathan L. Sessler、Peter Verwilst、Jong Seung Kim

  DOI：10.1016/j.chempr.2020.03.004

  日期：2020.6

  Tumor recurrence as a result of therapy-induced nuclear DNA lesions is a major issue in cancer treatment. Currently, only a few examples of potentially non-genotoxic drugs have been reported. Mitochondrial re-localization of ciprofloxacin, one of the most commonly prescribed synthetic antibiotics, is reported here as a new approach. Conjugation of ciprofloxacin to a triphenyl phosphonium group (giving lead Mt-CFX) is used to enhance the concentration of ciprofloxacin in the mitochondria of cancer cells. The localization of Mt-CFX to the mitochondria induces oxidative damage to proteins, mtDNA, and lipids. A large bias in favor of mtDNA damage over nDNA was seen with Mt-CFX, contrary to classic cancer chemotherapeutics. Mt-CFX was found to reduce cancer growth in a xenograft mouse model and proved to be well tolerated. Mitochondrial re-localization of antibiotics could emerge as a useful approach to generating anticancer leads that promote cell death via the selective induction of mitochondrially mediated oxidative damage.
• Haba, Keren; Popkov, Mikhail; Shamis, Marina, Angewandte Chemie - International Edition, 2005, vol. 44, # 5, p. 717 - 720
  作者：Haba, Keren、Popkov, Mikhail、Shamis, Marina、Lerner, Richard A.、Barbas, Carlos F.、Shabat, Doron

  DOI：——

  日期：——
• Cutting Off H⁺ Leaks on the Inner Mitochondrial Membrane: A Proton Modulation Approach to Selectively Eradicate Cancer Stem Cells
  作者：Minsu Park、Kyoung Sunwoo、Yoon-Jae Kim、Miae Won、Yunjie Xu、Jaewon Kim、Zhongji Pu、Mingle Li、Ji Young Kim、Jae Hong Seo、Jong Seung Kim

  DOI：10.1021/jacs.2c12587

  日期：2023.3.1