tert-butyl (2-(dihexadecylamino)ethyl)carbamate | 596789-62-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl (2-(dihexadecylamino)ethyl)carbamate
• 英文别名: tert-Butyl [2-(dihexadecylamino)ethyl]carbamate；tert-butyl N-[2-(dihexadecylamino)ethyl]carbamate
• CAS: 596789-62-7
• 化学式: C₃₉H₈₀N₂O₂
• 分子量: 609.076
• InChiKey: MNIJPDCGCQPPPI-UHFFFAOYSA-N

物化性质

• 沸点：
  654.3±38.0 °C(Predicted)
• 密度：
  0.880±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  16.5
• 重原子数：
  43
• 可旋转键数：
  35
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (2-(dihexadecylamino)ethyl)carbamate 在 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 65.0h， 生成 2-[[(8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthrene-17-carbonyl]amino]ethyl-dihexadecyl-methylazanium;chloride
  参考文献：
  名称：

  Cationic lipid-conjugated dexamethasone as a selective antitumor agent

  摘要：

  Dexamethasone (Dex) is one of the highly potent synthetic glucocorticoids. It exhibits prominent anti-inflammatory but moderate anti-proliferative activities. It is widely used along side chemotherapy to alleviate toxic side effects. Additionally, Dex is also a potent inducer of gluconeogenesis. However, its overuse critically desensitizes cells against chemotherapy. Herein, we report on the development of a new class of cationic lipid-Dex conjugates in which the C-8 carbon chain analogue (DX8) exhibited glucocorticoid receptor (GR)-mediated, caspase-3-assisted, cancer cell-selective anti-proliferative activity. Melanoma tumors in DX8-treated mice exhibited significantly reduced tumor aggressiveness with respect to tumors in Dex-treated mice. Tumor lysates prepared from DX8-treated group showed elevated levels of p53. DX8-treated cancer cells showed clear degradation of kinase JAK3/STAT3 protein levels. Additionally, DX8-treatment decreased the level of VEGFR2 in tumor-endothelial cells implying DX8's anti-proliferative roles in both tumor cells and tumor neovascular cells. Collectively, our results demonstrate potent anti-angiogenic, and selective JAK3/STAT3 down-regulating anticancer characteristics of DX8, a new dexamethasone-based antitumor molecule.

  DOI：

  10.1016/j.ejmech.2014.06.051
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 potassium carbonate 作用下， 以 乙酸乙酯 为溶剂， 生成 tert-butyl (2-(dihexadecylamino)ethyl)carbamate
  参考文献：
  名称：

  富含甲氧基的阳离子对苯二酚作为抗癌治疗剂。

  摘要：

  基于二苯乙烯的化合物的抗氧化活性被大量描述。但是，由于其不良的药代动力学特性以及对癌症的非选择性和非癌性，阻碍了它们用作抗癌化学疗法。为了克服这些缺点，设计，合成并评估了双链阳离子脂质共轭的，富含甲氧基的二苯乙烯衍生物，并评估了它们的抗癌效力。我们的发现表明，与其他合成衍生物和市售的基于二苯乙烯的药物相比，具有最多甲氧基和C16双链脂质的分子HMSC16是最有效和最具选择性的抗癌剂，他莫昔芬和白藜芦醇。为了证明这些结果的合理性，我们进行了一系列的机械实验，发现HMSC16诱导了ROS的产生，凋亡，并通过影响线粒体，溶酶体和核途径自噬。进一步的细胞周期分析数据表明，HMSC16不仅诱导细胞死亡，而且还参与了亚G1期细胞周期的停滞。此外，由于可能有利的亲水-亲脂平衡，HMSC16显示出自聚集性质。HMSC16的自聚集特性使其可以包埋疏水性药物阿瑟芬。包埋有ferferin的HMSC16在HeL

  DOI：

  10.1016/j.bioorg.2020.103719

文献信息

• Cationic lipid-conjugated hydrocortisone as selective antitumor agent
  作者：Bhowmira Rathore、Madhan Mohan Chandra Sekhar Jaggarapu、Anirban Ganguly、Hari Krishna Reddy Rachamalla、Rajkumar Banerjee

  DOI：10.1016/j.ejmech.2015.11.033

  日期：2016.1

  Hydrocortisone, the endogenously expressed steroidal, hormonal ligand for glucocorticoid receptor (GR), is body's natural anti-inflammatory and xenobiotic metabolizing agent. It has both palliative as well as adverse effects in different cancer patients. Herein, we show that conjugation product of C16-carbon chain-associated cationic lipid and hydrocortisone (namely, HYC16) induces selective toxicity in cancer (e.g. melanoma, breast cancer and lung adenocarcinoma) cells with least toxicity in normal cells, through induction of apoptosis and cell cycle arrest at G2/M phase. Further, significant tumor growth inhibition was observed in syngeneic melanoma tumor model with considerable induction of apoptosis in tumor associated cells. In contrast to hydrocortisone, significantly higher anti-angiogenic behavior of HYC16 helped in effective tumor shrinkage. This is the first demonstration to convert natural hormone hydrocortisone into a selective bioactive entity possessing anti-tumor effect. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Spatial Position Regulates Power of Tryptophan: Discovery of a Major-Groove-Specific Nuclear-Localizing, Cell-Penetrating Tetrapeptide
  作者：Debmalya Bhunia、Prasenjit Mondal、Gaurav Das、Abhijit Saha、Pallabi Sengupta、Jagannath Jana、Saswat Mohapatra、Subhrangsu Chatterjee、Surajit Ghosh

  DOI：10.1021/jacs.7b10254

  日期：2018.2.7

  Identification of key amino acids is required for development of efficient cell-penetrating peptides (CPPs) and has tremendous implications in medicine. Extensive research work has enlightened us about the importance of two amino acids, arginine and tryptophan, in cell penetration. Here, we present a top-down approach to show how spatial positions of two tryptophans regulate the cellular entry and nuclear localization. This enables us to develop short, non-toxic tetrapeptides with excellent potential for cell penetration and nuclear localization. Among them, Glu-Thr-Trp-Trp (ETWW) emerges as the most promising. Results suggest that it enters into cancer cells following an endocytic pathway and binds at the major groove of nuclear DNA, where successive tryptophan plays major role. We subsequently show that it is not a P-glycoprotein substrate and is non-toxic to PC12-derived neurons, suggesting its excellent potential as a CPP. Furthermore, its potential as a CPP is validated in multi-cellular 3D cell culture (spheroid) and in in vivo mice model. This study provides major fundamental insights' about the positional importance of tryptophan and opens new avenues toward the development of next-generation CPPs and major-groove-specific anticancer drugs.
• Methoxy-enriched cationic stilbenes as anticancer therapeutics
  作者：Md Yousuf、Sudhakar Jinka、Susanta Sekhar Adhikari、Rajkumar Banerjee

  DOI：10.1016/j.bioorg.2020.103719

  日期：2020.5

  anticancer chemotherapeutics is hampered by poor pharmacokinetic properties and non-selectivity towards cancer and non-cancer potency. To overcome these drawbacks, twin chain cationic lipid conjugated, methoxy-enriched stilbene derivatives were designed, synthesized and evaluated for their anticancer potency. Our findings reveal that HMSC16, a molecule with the highest number of methoxy groups and with

  基于二苯乙烯的化合物的抗氧化活性被大量描述。但是，由于其不良的药代动力学特性以及对癌症的非选择性和非癌性，阻碍了它们用作抗癌化学疗法。为了克服这些缺点，设计，合成并评估了双链阳离子脂质共轭的，富含甲氧基的二苯乙烯衍生物，并评估了它们的抗癌效力。我们的发现表明，与其他合成衍生物和市售的基于二苯乙烯的药物相比，具有最多甲氧基和C16双链脂质的分子HMSC16是最有效和最具选择性的抗癌剂，他莫昔芬和白藜芦醇。为了证明这些结果的合理性，我们进行了一系列的机械实验，发现HMSC16诱导了ROS的产生，凋亡，并通过影响线粒体，溶酶体和核途径自噬。进一步的细胞周期分析数据表明，HMSC16不仅诱导细胞死亡，而且还参与了亚G1期细胞周期的停滞。此外，由于可能有利的亲水-亲脂平衡，HMSC16显示出自聚集性质。HMSC16的自聚集特性使其可以包埋疏水性药物阿瑟芬。包埋有ferferin的HMSC16在HeL
• Cationic lipid-conjugated dexamethasone as a selective antitumor agent
  作者：Samaresh Sau、Rajkumar Banerjee

  DOI：10.1016/j.ejmech.2014.06.051

  日期：2014.8

  Dexamethasone (Dex) is one of the highly potent synthetic glucocorticoids. It exhibits prominent anti-inflammatory but moderate anti-proliferative activities. It is widely used along side chemotherapy to alleviate toxic side effects. Additionally, Dex is also a potent inducer of gluconeogenesis. However, its overuse critically desensitizes cells against chemotherapy. Herein, we report on the development of a new class of cationic lipid-Dex conjugates in which the C-8 carbon chain analogue (DX8) exhibited glucocorticoid receptor (GR)-mediated, caspase-3-assisted, cancer cell-selective anti-proliferative activity. Melanoma tumors in DX8-treated mice exhibited significantly reduced tumor aggressiveness with respect to tumors in Dex-treated mice. Tumor lysates prepared from DX8-treated group showed elevated levels of p53. DX8-treated cancer cells showed clear degradation of kinase JAK3/STAT3 protein levels. Additionally, DX8-treatment decreased the level of VEGFR2 in tumor-endothelial cells implying DX8's anti-proliferative roles in both tumor cells and tumor neovascular cells. Collectively, our results demonstrate potent anti-angiogenic, and selective JAK3/STAT3 down-regulating anticancer characteristics of DX8, a new dexamethasone-based antitumor molecule.