tert-butyl (4-((tert-butoxycarbonyl)amino)butyl)(4-(1,3-dioxoisoindolin-2-yl)butyl)carbamate | 950684-32-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: tert-butyl (4-((tert-butoxycarbonyl)amino)butyl)(4-(1,3-dioxoisoindolin-2-yl)butyl)carbamate
• CAS: 950684-32-9
• 化学式: C₂₆H₃₉N₃O₆
• 分子量: 489.612
• InChiKey: UEKSAMGZCZUGDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  35.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  105.25
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (4-((tert-butoxycarbonyl)amino)butyl)(4-(1,3-dioxoisoindolin-2-yl)butyl)carbamate 在 sodium tetrahydroborate 、 一水合肼 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Synthesis and bioevaluation of N-(arylalkyl)-homospermidine conjugates

  摘要：

  N'-(Arylalkyl)homospermidines (Ic-1f) and terminally piperazine-substituted homospermidine conjugates (2a-2e) were synthesized and evaluated for cytotoxicity in mouse leukemia L 1210, alpha-difluorometliylornithine (DFMO)-treated L 12 10, melanoma B 16, spermidine (SPD)-treated B 16, and HeLa cell lines. Results demonstrated that homospermidine was a more effective vector than piperazine-substituted homospermidine in ferrying diverse arenes into cells via the polyamine transporter. The leading compound, 9-anthracenemethyl-homospermidine (1a), was shown to induce apoptosis in B16 cells and IL-3 dependent FL5.12A proB cells. The novel conjugate 4-biphenylmethyl-homospermidine (1e) could also induce apoptosis. However, it exhibited different effect on the cell cycle of B16 cells compared to la. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.06.009
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 24.25h， 生成 tert-butyl (4-((tert-butoxycarbonyl)amino)butyl)(4-(1,3-dioxoisoindolin-2-yl)butyl)carbamate
  参考文献：
  名称：

  萘内酰亚胺-多胺缀合物及其制备方法和用途

  摘要：

  一类萘内酰亚胺‑多胺缀合物及其制备方法及用途，属于药物化学技术领域，所述萘内酰亚胺‑多胺缀合物具有如下结构：，其中R1为、、、、、、、、、、、,R2为，n为1或2，X为2、3、4、5或6。本申请以萘内酰亚胺为原料，在其芳环上6‑位引入各种芳环或者芳香杂环，并以碱性含氮小分子修饰内酰亚胺中氮原子，合成新的萘内酰亚胺萘内酰亚胺‑多胺缀合物。该类化合物改善了原有分子萘内酰亚胺的生物学活性，提高了目标分子的抗肿瘤活性。

  公开号：

  CN109665987B

文献信息

• A naphthalimide-polyamine conjugate preferentially accumulates in hepatic carcinoma metastases as a lysosome-targeted antimetastatic agent
  作者：Jing Ma、Linrong Li、Kexin Yue、Zhansheng Zhang、Shihao Su、Yutong Chen、Lu Yu、Pengfei Zhang、Ruijuan Ma、Yingguang Li、Yinxia Ma、Huinan Jia、Chaojie Wang、Jiajia Wang、Songqiang Xie

  DOI：10.1016/j.ejmech.2021.113469

  日期：2021.10
• Polyamine-Based Pt(IV) Prodrugs as Substrates for Polyamine Transporters Preferentially Accumulate in Cancer Metastases as DNA and Polyamine Metabolism Dual-Targeted Antimetastatic Agents
  作者：Hanfang Liu、Jing Ma、Yingguang Li、Kexin Yue、Linrong Li、Zhuoqing Xi、Xiao Zhang、Jianing Liu、Kai Feng、Qi Ma、Sitong Liu、Shudi Guo、Peng George Wang、Chaojie Wang、Songqiang Xie

  DOI：10.1021/acs.jmedchem.9b01641

  日期：2019.12.26

  Diverse platinum drug candidates have been designed to improve inhibitory potency and overcome resistance for orthotopic tumors. However, the antimetastatic properties have rarely been reported. We herein report that homospermidineplatin (4a), a polyamine-Pt(W) prodrug, can potently inhibit tumor growth in situ and reverse cisplatin resistance as expected, and more importantly, 4a displays remarkably elevated antimetastatic activity in vivo (65.7%), compared to those of cisplatin (27.0%) and oxaliplatin (19.6%). The underlying molecular mechanism indicates that in addition to targeting nuclear DNA, 4a can modulate polyamine metabolism and function in a manner different from that of cisplatin. By upregulating SSAT and PAO, 4a downregulates the concentrations of Put, Spd, and Spm, which favors the suppression of fast-growing tumor cells. Moreover, the p53/SSAT/beta-catenin and PAO/ROS/GSH/GSH-Px pathways are involved in the inhibition of 4a-induced tumor metastasis. Our study implies a promising strategy for the design of platinum drugs for the treatment of terminal cancer.