5-(1,2-dithiolan-3-yl)-N-phenylpentanamide | 109598-26-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫杂环戊烷
• 英文名称: 5-(1,2-dithiolan-3-yl)-N-phenylpentanamide
• 英文别名: 5-[1,2]dithiolan-3-yl-valeric acid anilide；5-[1,2]Dithiolan-3-yl-valeriansaeure-anilid；dl-1,2-Dithiolan-3-valeriansaeure-anilid；Thioctanilid；5-(dithiolan-3-yl)-N-phenylpentanamide
• CAS: 109598-26-7；1027-31-2
• 化学式: C₁₄H₁₉NOS₂
• 分子量: 281.443
• InChiKey: AKVBIWYAYFNJPW-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：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  79.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(1,2-dithiolan-3-yl)-N-phenylpentanamide 在 sodium tetrahydroborate 、 水 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 S,S'-(8-anilino-8-oxooctane-1,3-diyl)diethanethioate
  参考文献：
  名称：

  Synthesis, antiproliferation, and docking studies of N-phenyl-lipoamide and 8-mercapto-N-phenyloctanamide derivatives: effects of C6 position thiol moiety

  摘要：

  Some N-phenyl lipoamide and 8-mercapto-N-phenyloctanamide derivatives were synthesized and their in vitro antiproliferative activity was evaluated. The experimental results indicated that 8-mercapto-N-phenyloctanamides might be good histone deacetylase inhibitors rather than N-phenyl lipoamides, who had thiol moiety at C6 position. To verify the antiproliferation data on structural basis, in silico docking studies of the representative compounds into the crystal structure of histone deacetylase-like protein using AutoDock 4.0 program were performed. Furthermore, sulfur acetylated 8-mercapto-N-phenyloctanamide improved its in vitro antiproliferative activity, probably due to the increasing of its cell membrane permeability. While the identification of enzymatic target of N-phenyl lipoamides with dithiolane is still ongoing.

  DOI：

  10.1007/s00044-011-9879-7
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 1,4-二氧六环 、 苯胺 作用下， 生成 5-(1,2-dithiolan-3-yl)-N-phenylpentanamide
  参考文献：
  名称：

  Reed et al., Journal of Biological Chemistry, 1958, vol. 232, p. 143,144

  摘要：

  DOI：

文献信息

• Synthesis and anticancer evaluation of α-lipoic acid derivatives
  作者：Shi-Jie Zhang、Qiu-Fu Ge、Dian-Wu Guo、Wei-Xiao Hu、Hua-Zhang Liu

  DOI：10.1016/j.bmcl.2010.03.112

  日期：2010.5

  α-Lipoic acid derivatives were synthesized and evaluated for their in vitro anticancer activities against NCI-460, HO-8910, KB, BEL-7402, and PC-3 cell lines. The results, for most compounds exhibited dose-dependent inhibitory property and several compounds had good inhibitions at the dose of 100 μg/mL. Compound 17m was further selected for in vivo evaluation against S180 xenograft in ICR mice, which

  合成了α-硫辛酸衍生物，并评估了其对NCI-460，HO-8910，KB，BEL-7402和PC-3细胞系的体外抗癌活性。结果，对于大多数化合物而言，它们表现出剂量依赖性的抑制特性，并且几种化合物在100μg/ mL的剂量下具有良好的抑制作用。进一步选择化合物17m用于针对ICR小鼠中的S180异种移植物的体内评估，该化合物通过200mg / kg体重的胃内给药具有24.7％的肿瘤重量抑制。此外，LD 50在小鼠17米通过IG超过1000毫克/公斤体重。
• Secondary-Structure-Driven Self-Assembly of Reactive Polypept(o)ides: Controlling Size, Shape, and Function of Core Cross-Linked Nanostructures
  作者：Kristina Klinker、Olga Schäfer、David Huesmann、Tobias Bauer、Leon Capelôa、Lydia Braun、Natascha Stergiou、Meike Schinnerer、Anjaneyulu Dirisala、Kanjiro Miyata、Kensuke Osada、Horacio Cabral、Kazunori Kataoka、Matthias Barz

  DOI：10.1002/anie.201702624

  日期：2017.8.1

  function of polymeric nanostructures during self‐assembly remains a challenge in materials as well as biomedical science, especially when independent control over particle properties is desired. Herein, we report on nanostructures derived from amphiphilic block copolypept(o)ides by secondary‐structure‐directed self‐assembly, presenting a strategy to adjust core polarity and function separately from particle

  在自组装过程中实现对聚合物纳米结构的形态和功能的精确控制在材料以及生物医学科学中仍然是一个挑战，尤其是当需要对颗粒性质进行独立控制时。在本文中，我们报告了通过二级结构定向自组装衍生自两亲性嵌段共聚多肽（o）的纳米结构，提出了一种以生物可逆方式独立于颗粒制备来调节核心极性和功能的策略。肽固有的二级结构形成过程允许从同一嵌段共聚物合成球形和蠕虫状的核交联结构，从而为通用的基于肽的核壳纳米结构引入了一种简单而有效的方法。
• A comparative assessment of α-lipoic acid N-phenylamides as non-steroidal androgen receptor antagonists both on and off gold nanoparticles
  作者：Luke C. Henderson、Jarrad M. Altimari、Gail Dyson、Linden Servinis、Birunthi Niranjan、Gail P. Risbridger

  DOI：10.1016/j.bioorg.2011.11.007

  日期：2012.2

  A group of alpha-lipoic acid N-phenylamides were synthesized employing a variety of amide coupling protocols utilizing electron deficient anilines. These compounds were then assessed for their ability to block androgen-stimulated proliferation of a human prostate cancer cell line, LNCaP. These structurally simple compounds displayed anti-proliferative activities at, typically, 5-20 mu M concentrations and were comparable to a commonly used anti-androgen Bicalutamide (R). The inclusion of a disulfide (RS-SR) moiety, serving as an anchor to several metal nanoparticle systems (Au, Ag, Fe2O3, etc.), does not impede any biological activity. Conjugation of these compounds to a gold nanoparticle surface resulted in a high degree of cellular toxicity, attributed to the absence of a biocompatible group such as PEG within the organic scaffold. (C) 2011 Elsevier Inc. All rights reserved.
• Siemeling, Ulrich; Bretthauer, Frauke; Bruhn, Clemens, Zeitschrift fur Naturforschung, B: Chemical Sciences, 2010, vol. 65, # 9, p. 1089 - 1096
  作者：Siemeling, Ulrich、Bretthauer, Frauke、Bruhn, Clemens、Fellinger, Tim-Patrick、Tong, Wah-Leung、Chan, Michael C.W.

  DOI：——

  日期：——