Methyl 5-methyl-7-thia-2-azatricyclo[6.3.1.04,12]dodeca-1(12),3,8,10-tetraene-6-carboxylate | 148407-04-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: Methyl 5-methyl-7-thia-2-azatricyclo[6.3.1.04,12]dodeca-1(12),3,8,10-tetraene-6-carboxylate
• CAS: 148407-04-9
• 化学式: C₁₃H₁₃NO₂S
• 分子量: 247.318
• InChiKey: PPJMAHSZINPUCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  67.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl 5-methyl-7-thia-2-azatricyclo[6.3.1.04,12]dodeca-1(12),3,8,10-tetraene-6-carboxylate 在 N-甲基吗啉 sodium hydroxide 、 N-羟基-7-氮杂苯并三氮唑 、 盐酸羟胺 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-hydroxy-5-methyl-7-thia-2-azatricyclo[6.3.1.04,12]dodeca-1(12),3,8,10-tetraene-6-carboxamide
  参考文献：
  名称：

  The antimicrobial natural product chuangxinmycin and Some synthetic analogues are potent and selective inhibitors of bacterial tryptophanyl tRNA synthetase

  摘要：

  The antimicrobial natural product chuangxinmycin has been found to be a potent and selective inhibitor of bacterial tryptophanyl tRNA synthetase (WRS). A number of analogues have been synthesised. The interaction with WRS appears to be highly constrained, as only sterically smaller analogues afforded significant inhibition. The only analogue to show inhibition comparable to chuangxinmycin also had antibacterial activity. WRS inhibition may contribute to the antibacterial action of chuangxinmycin. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00604-2
• 作为产物：
  描述：

  1-(4-碘-1H-吲哚-3-基)-乙酮 在 sodium hydride 作用下， 生成 Methyl 5-methyl-7-thia-2-azatricyclo[6.3.1.04,12]dodeca-1(12),3,8,10-tetraene-6-carboxylate
  参考文献：
  名称：

  The antimicrobial natural product chuangxinmycin and Some synthetic analogues are potent and selective inhibitors of bacterial tryptophanyl tRNA synthetase

  摘要：

  The antimicrobial natural product chuangxinmycin has been found to be a potent and selective inhibitor of bacterial tryptophanyl tRNA synthetase (WRS). A number of analogues have been synthesised. The interaction with WRS appears to be highly constrained, as only sterically smaller analogues afforded significant inhibition. The only analogue to show inhibition comparable to chuangxinmycin also had antibacterial activity. WRS inhibition may contribute to the antibacterial action of chuangxinmycin. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00604-2

文献信息

• New, Concise Route to Indoles Bearing Oxygen or Sulfur Substituent at the 4-Position. Synthesis of (.+-.)- and (S)-(-)-Pindolol and (.+-.)-Chuangxinmycin.
  作者：Hiroyuki ISHIBASHI、Susumu AKAMATSU、Hiroko IRIYAMA、Kyoko HANAOKA、Takashi TABATA、Masazumi IKEDA

  DOI：10.1248/cpb.42.271

  日期：——

  A new method for the synthesis of 4-alkoxy- and 4-[alkyl (or aryl)thio]indoles has been developed by using the indolone 3 as a common intermediate. The indolone 3 was prepared from N-(phenylsulfonyl)pyrrole (7) and the α-chlorosulfide 8 in four steps. Heating of a mixture of 3 and an appropriate alcohol in the presence of p-toluenesulfonic acid and cupric chloride afforded the 4-alkoxyindoles 11a-d. The method was applied to the synthesis of (±)-pindolol (19) and (S)-(-)-pindolol (20). Thiols also reacted with 3 in the presence of boron trifluoride to give 4-[aryl (or alkyl)thio]indoles 12, 21a, b, and 22a-d. The (indol-4-ylthio)acetate 22c was employed as a key intermediate for a concise total synthesis of (±)-chuangxinmycin (27).

  一种新的合成4-烷氧基和4-[烷基（或芳基）硫代]吲哚的方法已被开发出来，该方法使用吲哚酮3作为共同中间体。吲哚酮3是通过N-(苯磺酰基)吡咯（7）和α-氯磺化物8经过四步反应制备的。在甲苯磺酸和氯化铜的存在下，将3与适当的醇混合并加热，得到了4-烷氧基吲哚11a-d。该方法被应用于合成（±）-吲哚洛尔（19）和（S）-(-)-吲哚洛尔（20）。硫醇在氟硼酸的存在下也能与3反应，生成4-[芳基（或烷基）硫代]吲哚12、21a、b以及22a-d。（吲哚-4-基硫代）乙酸酯22c被用作合成（±）-创新霉素（27）的关键中间体。
• A new, general entry to 4-substituted indoles. Synthesis of (S)-(−)-pindolol and (±)-chuangxinmycin
  作者：Hiroyuki Ishibashi、Takashi Tabata、Kyoko Hanaoka、Hiroko Iriyama、Susumu Akamatsu、Masazumi Ikeda

  DOI：10.1016/0040-4039(93)85109-a

  日期：1993.1

  A new method for synthesis of 4-substituted indoles has been developed by using the 7-arylthio-6-7-dihydroindol-4(5H) one5 as a common intermediate. The method was applied to the synthesis of (S)-(−)-pindolol (11) and (±)-chuangxinmycin (16).

  通过使用7-芳硫基-6-7-二氢吲哚-4（5 H）和5作为共同的中间体，已经开发了一种合成4-取代的吲哚的新方法。该方法适用于（S）-（-）-哌多洛尔（11）和（±）-创新霉素（16）的合成。
• MATSUMOTO, MASAKATSU;WATANABE, NOBUKO, HETEROCYCLES, 26,(1987) N 4, 913-916
  作者：MATSUMOTO, MASAKATSU、WATANABE, NOBUKO

  DOI：——

  日期：——
• The antimicrobial natural product chuangxinmycin and Some synthetic analogues are potent and selective inhibitors of bacterial tryptophanyl tRNA synthetase
  作者：Murray J. Brown、Paul S. Carter、Ashley E. Fenwick、Andrew P. Fosberry、Dieter W. Hamprecht、Martin J. Hibbs、Richard L. Jarvest、Lucy Mensah、Peter H. Milner、Peter J. O'Hanlon、Andrew J. Pope、Christine M. Richardson、Andrew West、David R. Witty

  DOI：10.1016/s0960-894x(02)00604-2

  日期：2002.11

  The antimicrobial natural product chuangxinmycin has been found to be a potent and selective inhibitor of bacterial tryptophanyl tRNA synthetase (WRS). A number of analogues have been synthesised. The interaction with WRS appears to be highly constrained, as only sterically smaller analogues afforded significant inhibition. The only analogue to show inhibition comparable to chuangxinmycin also had antibacterial activity. WRS inhibition may contribute to the antibacterial action of chuangxinmycin. (C) 2002 Elsevier Science Ltd. All rights reserved.