asterubine | 6249-86-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: asterubine
• 英文别名: 2-[[Amino(dimethylamino)methylidene]amino]ethanesulfonic acid；2-[[amino(dimethylamino)methylidene]amino]ethanesulfonic acid
• CAS: 6249-86-1
• 化学式: C₅H₁₃N₃O₃S
• 分子量: 195.243
• InChiKey: YPQPLVJIEOJFAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  asterubine 、 alkaline earth salt of/the/ methylsulfuric acid 生成 胍
  参考文献：
  名称：

  Ackermann, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, vol. 232, p. 206,210,211

  摘要：

  DOI：
• 作为产物：
  描述：

  bis-[2-(N',N'-dimethyl-guanidino)-ethyl]-disulfide 在 ferrous ammonium sulphate 、 水 、 双氧水 作用下， 生成 asterubine
  参考文献：
  名称：

  Ackermann; Mueller, Hoppe-Seyler´s Zeitschrift für physiologische Chemie, 1935, vol. 235, p. 234

  摘要：

  DOI：

文献信息

• Isolation and synthesis of N-acyladenine and adenosine alkaloids from a southern Australian marine sponge, Phoriospongia sp.
  作者：Michelle Farrugia、Nicholas Trotter、Soumini Vijayasarathy、Angela A. Salim、Zeinab G. Khalil、Ernest Lacey、Robert J. Capon

  DOI：10.1016/j.tetlet.2014.08.116

  日期：2014.10

  Chemical fractionation of the southern Australian marine sponge Phoriospongia sp. (CMB-03107) yielded phorioadenine A (1) as a nematocidal agent and the first reported example of a 6-N-acyladenine natural product. The structure of 1 was confirmed by spectroscopic analysis and the chemical synthesis of racemic (1a) and enantiomeric (1b) analogues. HPLC-ESIMS analysis of the crude sponge extract with comparisons to the synthetic 6-N-acyladenosine 2a provided evidence that the biosynthetically related adenosine, phorioadenosine A (2), was present as a trace co-metabolite. The rare starfish metabolite asterubine (3) was also isolated as a co-metabolite, and its structure confirmed by spectroscopic analysis and chemical synthesis. Biological investigations confirmed that natural products 1-3 and synthetic analogues la-e and 2a were not cytotoxic to multiple mammalian cancer cell lines, or Gram-positive or -negative bacteria. Nematocidal activity (inhibition of larval development of Haemonchus contortus) detected in the Phoriospongia sp. extract was attributed to 1 (LD99 31 mu g/mL), with preliminary structure-activity relationship investigations confirming the importance of the N-acyl side chain. (C) 2014 Elsevier Ltd. All rights reserved.
• Ackermann, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1935, vol. 234, p. 208
  作者：Ackermann

  DOI：——

  日期：——