2-(2,3-dihydro-1H-indole-1-sulfonyl)aniline | 954587-88-3

• 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: 2-(2,3-dihydro-1H-indole-1-sulfonyl)aniline
• 英文别名: 1-(2-aminobenzenesulfonyl)indoline；2-(2,3-Dihydroindol-1-ylsulfonyl)aniline
• CAS: 954587-88-3
• 化学式: C₁₄H₁₄N₂O₂S
• 分子量: 274.343
• InChiKey: QZHVUXBIVPBGRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2,3-dihydro-1H-indole-1-sulfonyl)aniline 在 N-碘代丁二酰亚胺 作用下， 以 1,2-二氯乙烷 为溶剂， 以68 %的产率得到9-iodo-1,12a-dihydro-12H-benzo[e]indolino[1,2-b][1,2,4]thiadiazine 7,7-dioxide
  参考文献：
  名称：

  通过 sp3-CH 激活作为潜在结肠癌抑制剂的新型三环和角四环苯并噻二嗪的合成和分子对接研究

  摘要：

  本文描述了三环和四环苯并噻二嗪及其衍生物的合成，这些衍生物因其作为生物活性剂的多功能性而闻名。起始原料为N-环氨基-4-取代-2-硝基苯磺酰胺8-16，由4-取代-2-硝基苯磺酰氯1-3和环胺4-7缩合制备。中间体 N-环氨基-4-取代-2-磺酰胺 17-25 是通过使用 10% 钯炭催化剂催化氢化 N-环氨基-4-取代-2-硝基苯磺酰胺 8-16 获得的。然后通过无金属分子内 N-碘代琥珀酰亚胺 (NIS) 介导的自由基氧化sp 3 -CH合成具有潜在生物活性的三环和角四环 1,2,4-苯并噻二嗪二氧化物 26-34N-环氨基-4-取代-2-磺酰胺 17-25 的活化氨基环化。产量从好到极好（68-93%）。对 N-环氨基-4-取代-2-硝基苯磺酰胺 8-16、N-环氨基-4-取代-2-磺酰胺 17-25 以及三环和角四环 1,2,4-苯并噻二嗪二氧化物 26- 进行对接研究34 使用五

  DOI：

  10.1002/jhet.4715
• 作为产物：
  描述：

  邻硝基苯磺酰氯 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 、 甲苯 为溶剂， 生成 2-(2,3-dihydro-1H-indole-1-sulfonyl)aniline
  参考文献：
  名称：

  通过 sp3-CH 激活作为潜在结肠癌抑制剂的新型三环和角四环苯并噻二嗪的合成和分子对接研究

  摘要：

  本文描述了三环和四环苯并噻二嗪及其衍生物的合成，这些衍生物因其作为生物活性剂的多功能性而闻名。起始原料为N-环氨基-4-取代-2-硝基苯磺酰胺8-16，由4-取代-2-硝基苯磺酰氯1-3和环胺4-7缩合制备。中间体 N-环氨基-4-取代-2-磺酰胺 17-25 是通过使用 10% 钯炭催化剂催化氢化 N-环氨基-4-取代-2-硝基苯磺酰胺 8-16 获得的。然后通过无金属分子内 N-碘代琥珀酰亚胺 (NIS) 介导的自由基氧化sp 3 -CH合成具有潜在生物活性的三环和角四环 1,2,4-苯并噻二嗪二氧化物 26-34N-环氨基-4-取代-2-磺酰胺 17-25 的活化氨基环化。产量从好到极好（68-93%）。对 N-环氨基-4-取代-2-硝基苯磺酰胺 8-16、N-环氨基-4-取代-2-磺酰胺 17-25 以及三环和角四环 1,2,4-苯并噻二嗪二氧化物 26- 进行对接研究34 使用五

  DOI：

  10.1002/jhet.4715

文献信息

• Reduction of arenediazonium salts by tetrakis(dimethylamino)ethylene (TDAE): Efficient formation of products derived from aryl radicals
  作者：Mohan Mahesh、John A Murphy、Franck LeStrat、Hans Peter Wessel

  DOI：10.3762/bjoc.5.1

  日期：——

  arenediazonium salts to aryl radical intermediates through a single electron transfer (SET) pathway. Cyclization of the aryl radicals produced in this way led, in appropriate substrates, to syntheses of indolines and indoles. Cascade radical cyclizations of aryl radicals derived from arenediazonium salts are also reported. The relative ease of removal of the oxidized by-products of TDAE from the reaction

  四（二甲氨基）乙烯（TDAE 1）首次被用作一种温和的试剂，用于通过单电子转移（SET）途径将芳烃重氮盐还原为芳基自由基中间体。以这种方式产生的芳基环化导致在适当的底物中合成二氢吲哚和吲哚。还报道了衍生自芳烃重氮盐的芳基的级联自由基环化。从反应混合物中去除 TDAE 的氧化副产物相对容易，这使得该方法具有综合吸引力。
• Synthesis, crystal structure and in-silico evaluation of arylsulfonamide Schiff bases for potential activity against colon cancer
  作者：Sherif O. Kolade、Oluwafemi S. Aina、Allen T. Gordon、Eric C. Hosten、Idris A. Olasupo、Adeniyi S. Ogunlaja、Olayinka T. Asekun、Oluwole B. Familoni

  DOI：10.1107/s205322962400233x

  日期：2024.4.1

  This report presents a comprehensive investigation into the synthesis and characterization of Schiff base compounds derived from benzenesulfonamide. The synthesis process, involved the reaction between N-cycloamino-2-sulfanilamide and various substituted o-salicylaldehydes, resulted in a set of compounds that were subjected to rigorous characterization using advanced spectral techniques, including 1H NMR, 13C NMR and FT–IR spectroscopy, and single-crystal X-ray diffraction. Furthermore, an in-depth assessment of the synthesized compounds was conducted through Absorption, Distribution, Metabolism, Excretion and Toxicity (ADMET) analysis, in conjunction with docking studies, to elucidate their pharmacokinetic profiles and potential. Impressively, the ADMET analysis showcased encouraging drug-likeness properties of the newly synthesized Schiff bases. These computational findings were substantiated by molecular properties derived from density functional theory (DFT) calculations using the B3LYP/6-31G* method within the Jaguar Module of Schrödinger 2023-2 from Maestro (Schrodinger LLC, New York, USA). The exploration of frontier molecular orbitals (HOMO and LUMO) enabled the computation of global reactivity descriptors (GRDs), encompassing charge separation (E gap) and global softness (S). Notably, within this analysis, one Schiff base, namely, 4-bromo-2-N-[2-(pyrrolidine-1-sulfonyl)phenyl]carboximidoyl}phenol, 20, emerged with the smallest charge separation (ΔE gap = 3.5780 eV), signifying heightened potential for biological properties. Conversely, 4-bromo-2-N-[2-(piperidine-1-sulfonyl)phenyl]carboximidoyl}phenol, 17, exhibited the largest charge separation (ΔE gap = 4.9242 eV), implying a relatively lower propensity for biological activity. Moreover, the synthesized Schiff bases displayed remarkeable inhibition of tankyrase poly(ADP-ribose) polymerase enzymes, integral in colon cancer, surpassing the efficacy of a standard drug used for the same purpose. Additionally, their bioavailability scores aligned closely with established medications such as trifluridine and 5-fluorouracil. The exploration of molecular electrostatic potential through colour mapping delved into the electronic behaviour and reactivity tendencies intrinsic to this diverse range of molecules.