N-(phenylsulfonyl)-2-methoxalylindole | 75400-66-7

• 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: N-(phenylsulfonyl)-2-methoxalylindole
• 英文别名: N-benzenesulfonyl-2-methoxalylindole；Methyl oxo(1-(phenylsulfonyl)-1H-indol-2-yl)acetate；methyl 2-[1-(benzenesulfonyl)indol-2-yl]-2-oxoacetate
• CAS: 75400-66-7
• 化学式: C₁₇H₁₃NO₅S
• 分子量: 343.36
• InChiKey: FMXYYPVQVMPNGI-UHFFFAOYSA-N

物化性质

• 熔点：
  111-112 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  548.9±42.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  90.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(phenylsulfonyl)-2-methoxalylindole 在 sodium hydroxide 作用下， 以 乙醚 、 水 为溶剂， 反应 1.25h， 生成 2-methoxalylindole
  参考文献：
  名称：

  Synthesis and reactions of N-protected 2-lithiated pyrroles and indoles. The tert-butoxycarbonyl substituent as a protecting group

  摘要：

  DOI：

  10.1021/jo00314a034
• 作为产物：
  描述：

  吲哚 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.58h， 生成 N-(phenylsulfonyl)-2-methoxalylindole
  参考文献：
  名称：

  Synthesis and in vitro antitumor activity of novel 2-alkyl-5-methoxycarbonyl-11-methyl-6H-pyrido[4,3-b]carbazol-2-ium and 2-alkylellipticin-2-ium chloride derivatives

  摘要：

  Twenty-one types of novel ellipticine derivatives and pyridocarbazoles (5-methoxycarbonyl-11-methyl-6H-pyrido[4,3-b]carbazoles) with a nitrosourea moiety, linked by an oxydiethylene unit at the 2 position, were synthesized, and their cytotoxicity against HeLa S-3 cells was evaluated. Some of these new compounds exhibited potent antitumor activity by comparison with that of ellipticine. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.032

文献信息

• Stereoselective Synthesis of Trisubstituted Epoxides Marks the Route to Chiral Building Blocks with Quaternary Centers
  作者：Miguel Garcia-Castro、Murali Annamalai、Christopher Golz、Carsten Strohmann、Kamal Kumar

  DOI：10.1002/ejoc.201701148

  日期：2017.10.10

  A facile access to enantiomerically pure derivatives of α-hydroxy-β-amino acids bearing a quaternary center and trifluoromethylated tertiary alcohols which represent highly important building blocks to therapeutically relevant small molecules, was efficiently achieved by developing an asymmetric epoxidation of α-activated ketones by employing chiral sulfur ylides.

  通过开发α-活化酮的不对称环氧化，可以轻松获得带有季中心的α-羟基-β-氨基酸的对映体纯衍生物和代表治疗相关小分子非常重要的结构单元的三氟甲基化叔醇。使用手性硫叶立德。
• Synthesis of navelbine analogs
  申请人：Board of Regents, The University of Texas System

  公开号：US05220016A1

  公开（公告）日：1993-06-15

  The invention is a de novo synthesis of the norcatharanthine moiety of navelbine. The synthesis includes condensing a Grignard reagent prepared from an amine-protected R(+)-piperidinyl methanol with an N-protected 2-methoxyoxalyl indole. The indole N-protecting group is removed to provide a 2-methoxyindole hydroxy ester which is coupled to vindoline. After removal of the amineprotecting group from the piperidinyl group, ring closure to the indole moiety provides dihydrodesethyl navelbine. Other derivatives and analogs of navelbine with potential clinical applications in cancer chemotherapy may be readily synthesized. The synthesis opens a route to a wide variety of navelbine modifications, including modifications at or near the tryptamine bridge.

  本发明是关于紫杉醇的主体norcatharanthine的全新合成方法。该合成方法包括将一种来自氨基保护的R(+)-哌啶甲醇的Grignard试剂与N-保护的2-甲氧基草酰基吲哚缩合。去除吲哚N-保护基后，得到2-甲氧基吲哚羟基酯，该酯与长春碱偶联。去除哌啶基的氨基保护基后，环闭合到吲哚基团，形成二氢去乙基紫杉醇。可以轻松地合成紫杉醇的其他衍生物和类似物，这些衍生物和类似物具有在癌症化疗中的潜在临床应用。该合成方法打开了通往各种紫杉醇修饰的途径，包括在或接近色胺桥处的修饰。
• Synthesis of the vinblastine-like antitumor bis-indole alkaloid navelbine analog desethyldihydronavelbine
  作者：Philip Magnus、Lee S. Thurston

  DOI：10.1021/jo00003a045

  日期：1991.2

  (R)-(-)-Ethyl nipecotate 6 was converted into the N-allyl bromide 10 whose derived Grignard reagent 11 was added to N-(phenylsulfonyl)-2-(methoxyoxalyl)indole 12 to give the diastereomeric alcohols 13. Removal of the indole protecting group from 13 and coupling with vindoline gave the separable diastereomers 15(S) and 17(R). Deprotection of 15/17 and treatment with formaldehyde/acetic acid gave desethyldihydronavelbine 5, and its 18'-epimer 19. Only the natural 18'-epimer exhibited any antitumor activity.
• Synthesis of 6-substituted 7H-pyrido[4,3-c]carbazoles
  作者：Sandeep P. Modi、Abdel Hadi Zayed、Sydney Archer

  DOI：10.1021/jo00274a024

  日期：1989.6
• MODI, SANDEEP P.;ZAYED, ABDEL-HADI;ARCHER, SYDNEY, J. ORG. CHEM., 54,(1989) N3, C. 3084-3087
  作者：MODI, SANDEEP P.、ZAYED, ABDEL-HADI、ARCHER, SYDNEY

  DOI：——

  日期：——