purpurealidin E

• 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: purpurealidin E
• 英文别名: 3,5-dibromo-4-(3-dimethylaminopropoxy)phenethyl amine；3-[4-(2-aminoethyl)-2,6-dibromophenoxy]-N,N-dimethylpropan-1-amine
• 化学式: C₁₃H₂₀Br₂N₂O
• 分子量: 380.123
• InChiKey: DLVXRTCGFCRTMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.538
• 拓扑面积：
  38.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  藜芦酸 、 purpurealidin E 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Synthesis of novel purpurealidin analogs and evaluation of their effect on the cancer-relevant potassium channel KV10.1

  摘要：

  在寻找新型抗癌药物的过程中，钾通道 KV10.1 已成为一个有趣的癌症靶点。在此，我们报告了一组新的 KV10.1 抑制剂，即紫草素类似物。这些生物碱由马鞭草海绵产生，具有多种生物活性。在本研究中，我们介绍了 27 种紫草素类似物的合成和表征。从结构上看，中央苯环上的溴取代基和远端苯环上的甲氧基似乎能增强对 KV10.1 的活性。研究了最强类似物 5 的作用机制。研究人员观察到活化曲线向更负的电位移动以及明显的失活现象。由于 KV10.1 抑制剂可能是有趣的抗癌药物先导化合物，因此我们评估了 5 对癌症和非癌症细胞系的影响。化合物 5 具有细胞毒性，似乎能诱导所有被评估细胞株的细胞凋亡。

  DOI：

  10.1371/journal.pone.0188811
• 作为产物：
  描述：

  N,N-二甲氨基氯丙烷盐酸盐 在 potassium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 3.0h， 生成 purpurealidin E
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Purpurealidin E-Derived Marine Sponge Metabolites: Aplysamine-2, Aplyzanzine A, and Suberedamines A and B

  摘要：

  Five purpurealidin-derived marine secondary sponge metabolies have been synthesized through the carbodiimide coupling of an appropriate bromotyrosine unit. The structure elucidations have been confirmed through direct comparison with spectroscopic data of isolated natural products. Aplyzanzine A has been shown to be the most active product against a broad bacterial and fungal screen, demonstrating MIC values 2 to 4 times lower than the other metabolites in this study. Compounds 2, 3, 4a, and 5-7 exhibit a modest inhibition against slow growing mycobacteria (MIC 25-50 mu g/mL), including Mycobacterium tuberculosis. iso-Anomoian A and suberedamine B showed antitumor activity in the NCI-DTP60 cell line screen at single-digit micromolar concentrations, with iso-anomoian A inhibiting 53 cell lines. These molecules present novel scaffolds for further optimization.

  DOI：

  10.1021/np300102z

文献信息

• Synthesis and Antiproliferative Activity of Marine Bromotyrosine Purpurealidin I and Its Derivatives
  作者：Chinmay Bhat、Polina Ilina、Irene Tilli、Manuela Voráčová、Tanja Bruun、Victoria Barba、Nives Hribernik、Katja-Emilia Lillsunde、Eero Mäki-Lohiluoma、Tobias Rüffer、Heinrich Lang、Jari Yli-Kauhaluoma、Paula Kiuru、Päivi Tammela

  DOI：10.3390/md16120481

  日期：——

  Purpurealidin I (1) showed no selectivity but its simplified pyridin-2-yl derivative (36) had the best improvement in selectivity (Selectivity index 4.1). This shows that the marine bromotyrosines are promising scaffolds for developing cytotoxic agents and the full understanding of the elements of their SAR and improving the selectivity requires further optimization of simplified bromotyrosine derivatives.

  报道了使用三氟乙酰氧基保护基及其二甲基化类似物（29）的海洋溴酪氨酸purpurealidin I（1）的首次全合成，以及缺少酪胺部分的16种简化的溴酪氨酸衍生物。评估了它们对人类恶性黑色素瘤细胞系（A-375）和正常皮肤成纤维细胞（Hs27）的细胞毒性，以及33种由嘌呤释放素激发的简化酰胺，并研究了其结构活性关系。没有酪胺部分的合成的简化类似物保留了细胞毒活性。Purpurealidin I（1）没有显示出选择性，但其简化的吡啶-2-基衍生物（36）在选择性方面的改善最大（选择性指数4.1）。
• Chichibabin/isoChichibabin pyridinium synthesis of ma’edamines C and D
  作者：Mika Hirose、Nao Tanaka、Toyonobu Usuki

  DOI：10.1016/j.bmcl.2021.128165

  日期：2021.8

  an Okinawan marine sponge and exhibited a unique tetrasubstituted pyridinium skeleton. The proposed biosynthetic pathway is similar to that of desmosine and isodesmosine, which are elastin-crosslinking amino acids. In this study, first total synthesis of ma’edamines C and D was achieved via Pr(OTf)3-promoted Chichibabin/isoChichibabin pyridinium synthesis starting from the corresponding aldehydes and

  Ma'edamines C 和 D 是从冲绳海海绵中分离出来的，并表现出独特的四取代吡啶骨架。所提出的生物合成途径类似于弹性蛋白交联氨基酸地丝氨酸和异地丝氨酸的生物合成途径。在这项研究中，首先通过 Pr(OTf) 3促进的 Chichibabin/iso Chichibabin 吡啶鎓合成，从相应的醛和胺开始，实现了 Ma'edamines C 和 D 的全合成。
• Total Synthesis of Dispyrin, Purpurealidin E, and Aplysamine-1
  作者：Makoto Yoshida、Kentaro Yamaguchi

  DOI：10.1248/cpb.56.1362

  日期：——

  Bromotyrosine alkaloids dispyrin (1), purpurealidin E (2), and aplysamine-1 (3) isolated from marine sponge, were synthesized from commercially available tyramine (4) as a common starting material. The overall yield was 18%, 39%, and 22% for 1 from 4 in 5 steps, 2 in 5 steps, and 3 in 6 steps, respectively.

  以市面上常见的酪胺（4）为起始原料，合成了从海洋海绵中分离出来的溴代酪氨酸生物碱dispyrin（1）、purpurealidin E（2）和aplysamine-1（3）。通过 5 个步骤从 4 中合成 1，通过 5 个步骤合成 2，通过 6 个步骤合成 3，总收率分别为 18%、39% 和 22%。
• Efficient Synthesis of Tyrosine-Derived Marine Sponge Metabolites via Acylation of Amines with a Coumarin
  作者：J. Jonathan Harburn、Nigam P. Rath、Christopher D. Spilling

  DOI：10.1021/jo050846r

  日期：2005.8.1

  Condensation of N-acetylglycine with aldehyde 15 in acetic anhydride gave acetamido coumarin 16. Hydrolysis to the enol coumarin 17 and reaction with hydroxylamine gave the oximino coumarin 18. Reaction of the oximino coumarin 18 with a range of nucleophiles gave the phenolic oximes in excellent yield. The rates of acylation of histamine with the oximino coumarin 18 and methyl ester 9 were compared. Oxidative spirocyclization of three representative phenolic oximes with polymersupported (diacetoxyiodo) benzene gave the spiroisoxazolines.
• Versatile Routes to Marine Sponge Metabolites through Benzylidene Rhodanines
  作者：Suresh K. Kottakota、Mathew Benton、Dimitrios Evangelopoulos、Juan D. Guzman、Sanjib Bhakta、Timothy D. McHugh、Mark Gray、Paul W. Groundwater、Emma C. L. Marrs、John D. Perry、J. Jonathan Harburn

  DOI：10.1021/ol303057a

  日期：2012.12.21

  The first total synthesis of the marine natural products Psammaplin C and Tokaradine A is described. Benzylidene rhodanines were utilized as versatile intermediates toward the synthesis of seven brominated marine sponge metabolites through the optimization of protection group strategies. Spermatinamine demonstrated good inhibition of all cancer cell lines tested, in particular the leukemia K562 and colon cancer HT29 cell lines.