varacin | 134029-48-4

• 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: varacin
• 英文别名: 2-(6,7-dimethoxy-1,2,3,4,5-benzopentathiepin-9-yl)ethanamine
• CAS: 134029-48-4
• 化学式: C₁₀H₁₃NO₂S₅
• 分子量: 339.549
• InChiKey: HIKCOAGMCNIBMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  171
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-(+)-1-(1-萘基)乙基异氰酸酯 、 varacin 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 1-[2-(6,7-dimethoxy-1,2,3,4,5-benzopentathiepin-9-yl)ethyl]-3-[(1S)-1-naphthalen-1-ylethyl]urea
  参考文献：
  名称：

  不对称取代的苯并戊噻吩类化合物中的手性：对环反转的高势垒的结果

  摘要：

  伐拉星（1）的1 H NMR光谱显示出侧链亚甲基质子的信号出乎意料地复杂。提出的证据表明，由于高能垒阻碍了多硫化物环的低能椅子构象的转化，因此不对称取代的苯并五氢噻吩类化合物是不对称分子。缬氨酸的手性助剂衍生化提供了非对映体产物，其可以通过分级重结晶来分离。

  DOI：

  10.1016/0040-4039(94)85356-8
• 作为产物：
  描述：

  5-溴香兰素 在 吡啶 、 喹啉 、 二氯化二硫 、 lithium aluminium tetrahydride 、 ammonium acetate 、 氨 、 溴 、 sodium 、 四丁基碘化铵 、 potassium carbonate 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 溶剂黄146 为溶剂， 生成 varacin
  参考文献：
  名称：

  Synthesis of varacin, a cytotoxic naturally occurring benzopentathiepin isolated from a marine ascidian

  摘要：

  The total synthesis of varacin (1), a cytotoxic metabolite isolated from a marine ascidian, has been accomplished in 11 steps from vanillin, providing unambiguous confirmation of the unique dopamine-related benzopentathiepin structure.

  DOI：

  10.1021/jo00069a006

文献信息

• Synthesis and Structural Properties of the Benzopentathiepins Varacin and Isolissoclinotoxin A
  作者：Paul W. Ford、Mathew R. Narbut、Jack Belli、Bradley S. Davidson

  DOI：10.1021/jo00099a026

  日期：1994.10

  The unique pentathiepin-containing compounds varacin (1) and isolissoclinotoxin A (3) have each been synthesized in eight steps from vanillin. Formation of the pentathiepin ring in varacin was accomplished by treatment of the dithiolate anion, generated from the Na/NH3 reduction of bisbutyl sulfide intermediate 10, with 2 equiv of S2Cl2. Placement of the sulfur atoms on the aromatic ring was accomplished by treatment of 5,6-dibromovanillin (6) with cuprous n-butylmercaptide in pyridine/quinoline at 160 degrees C. The structure of the penultimate intermediate, TEOC-protected varacin (II), was confirmed by X-ray diffraction analysis. Isolissoclinotoxin A was prepared in an analogous manner, using a MOM group to protect the phenol. The structure of varacin has been confirmed; however, reductive acetylation of 3 yielded tetraacetate derivative 20, which was different than that reported as a product of lissoclinotoxin A acetylation. Because the data recorded for 20 did not match that previously reported, it is likely that the structure of lissoclinotoxin A should be reassigned to regioisomer 4, which has the phenol and methoxy group interchanged.
• DAVIDSON, BRADLEY S.;MOLINSKI, TADEUSZ F.;BARROWS, LOUIS R.;IRELAND, CHRI+, J. AMER. CHEM. SOC., 113,(1991) N2, C. 4709-4710
  作者：DAVIDSON, BRADLEY S.、MOLINSKI, TADEUSZ F.、BARROWS, LOUIS R.、IRELAND, CHRI+

  DOI：——

  日期：——
• Davidson Bradley S., Ford Paul W., Wahlman Magnus, Tetrahedron Lett, 35 (1994) N 39, S 7185-7188
  作者：Davidson Bradley S., Ford Paul W., Wahlman Magnus

  DOI：——

  日期：——
• Varacin: a novel benzopentathiepin from Lissoclinum vareau that is cytotoxic toward a human colon tumor
  作者：Bradley S. Davidson、Tadeusz F. Molinski、Louis R. Barrows、Chris M. Ireland

  DOI：10.1021/ja00012a065

  日期：1991.6
• Isodiplamine, cystodytin K and lissoclinidine: novel bioactive alkaloids from the New Zealand ascidian Lissoclinum notti
  作者：David R Appleton、A.Norrie Pearce、Gretchen Lambert、Russell C Babcock、Brent R Copp

  DOI：10.1016/s0040-4020(02)01296-6

  日期：2002.12

  A study of the bioactive crude extract of the New Zealand ascidian Lissoclinum notti led to the isolation of the new pyridoacridine alkaloids isodiplamine (4), cystodytin K (5) and lissoclinidine (6), as well as the known pyridoacridine alkaloids diplamine (7) and cystodytin J (8) and the benzopentathiepin varacin (3) and related trithiane varacin A. The new alkaloids were characterised using standard spectroscopic techniques, including 2D H-1-N-15 NMR experiments. Pyridoacridine alkaloids 4-8 were assayed for a range of biological activities including antitumour and antibiotic properties. (C) 2002 Elsevier Science Ltd. All rights reserved.