(2R)-3-(1,3-dithian-2-ylmethyl)-2-methylbut-3-enal | 1332640-96-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二噻烷
• 英文名称: (2R)-3-(1,3-dithian-2-ylmethyl)-2-methylbut-3-enal
• CAS: 1332640-96-6
• 化学式: C₁₀H₁₆OS₂
• 分子量: 216.368
• InChiKey: USDRUJBEYWQSFV-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R)-3-(1,3-dithian-2-ylmethyl)-2-methylbut-3-enal 在 potassium fluoride 、 sodium chlorite 、 copper(l) iodide 、 sodium dihydrogenphosphate dihydrate 、 2-甲基-2-丁烯 、 水 、 diethylzinc 、 N,N-二异丙基乙胺 、 三苯基膦 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 三氟乙酸 、 calcium carbonate 、 偶氮二甲酸二乙酯 、 碘甲烷 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 、 叔丁醇 为溶剂， 反应 53.41h， 生成 (6S,9S,14R,15R)-7,9,14-trimethyl-13-methylidene-15-[1-(naphthalen-2-ylmethyl)triazol-4-yl]-6-propan-2-yl-1-oxa-4,7,10-triazacyclopentadecane-2,5,8,11-tetrone
  参考文献：
  名称：

  Synthesis and biological evaluation of triazole analogues of antillatoxin

  摘要：

  Antillatoxin 1, a cyclic lipopeptide, is known as an activator of voltage-gated sodium channels and exhibits potent neurotoxicity toward Neuro 2a mouse neuroblastoma cells. To investigate the biological effects of the side-chain structures at C5 and C5' in detail, we planned SAR studies of C5- and C5'-modified antillatoxin analogues. To diversify the structures at the last step of the synthesis, two key intermediates 4 and 6 possessing terminal alkynes at the C5- and C5'-positions were designed and synthesized using two distinct strategies. Sixteen side-chain derivatives were then prepared from 4 and 6 by coupling with a wide variety of azides via click chemistry, and subjected to the cytotoxicity assay. Although almost all of the C5-substituted analogues exhibited no cytotoxicity, the C5'-substituted analogues showed modest cytotoxicity. These results showed that C5' is more tolerant than C5 to structural modifications. The present SAR study will provide valuable information for designing new antillatoxin-based molecular probes for neuroscience research. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.012

文献信息

• Synthesis and biological evaluation of triazole analogues of antillatoxin
  作者：Ryosuke Goto、Ken Okura、Hayato Sakazaki、Tatsuya Sugawara、Shigeru Matsuoka、Masayuki Inoue

  DOI：10.1016/j.tet.2011.05.012

  日期：2011.9

  Antillatoxin 1, a cyclic lipopeptide, is known as an activator of voltage-gated sodium channels and exhibits potent neurotoxicity toward Neuro 2a mouse neuroblastoma cells. To investigate the biological effects of the side-chain structures at C5 and C5' in detail, we planned SAR studies of C5- and C5'-modified antillatoxin analogues. To diversify the structures at the last step of the synthesis, two key intermediates 4 and 6 possessing terminal alkynes at the C5- and C5'-positions were designed and synthesized using two distinct strategies. Sixteen side-chain derivatives were then prepared from 4 and 6 by coupling with a wide variety of azides via click chemistry, and subjected to the cytotoxicity assay. Although almost all of the C5-substituted analogues exhibited no cytotoxicity, the C5'-substituted analogues showed modest cytotoxicity. These results showed that C5' is more tolerant than C5 to structural modifications. The present SAR study will provide valuable information for designing new antillatoxin-based molecular probes for neuroscience research. (C) 2011 Elsevier Ltd. All rights reserved.