1-(2-硝基苯基磺酰基)哌啶 | 314283-05-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(2-硝基苯基磺酰基)哌啶
• 英文名称: 2-nitrobenzenesulfopiperidide
• 英文别名: 1-(2-nitrophenylsulfonyl)piperidine；1-(2-nitrophenyl)piperidine；1-((2-Nitrophenyl)sulfonyl)piperidine；1-(2-nitrophenyl)sulfonylpiperidine
• CAS: 314283-05-1
• 化学式: C₁₁H₁₄N₂O₄S
• mdl: MFCD00514602
• 分子量: 270.309
• InChiKey: AACRWZVDRSTLKY-UHFFFAOYSA-N

物化性质

• 熔点：
  95 °C(Solv: ethanol (64-17-5))
• 沸点：
  436.6±47.0 °C(Predicted)
• 密度：
  1.374±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  91.6
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2935009090

反应信息

• 作为反应物：
  描述：

  1-(2-硝基苯基磺酰基)哌啶 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 以86%的产率得到1-[(2-氨基苯基)磺酰基]哌啶
  参考文献：
  名称：

  N-Cycloamino substituent effects on the packing architecture of ortho-sulfanilamide molecular crystals and their in silico carbonic anhydrase II and IX inhibitory activities

  摘要：

  为了寻找具有治疗特性的新型 "磺胺药物"，我们合成了邻硝基磺酰胺和 N-环氨基邻磺酰苯胺，并利用 1H NMR、13C NMR 和 FT-IR 光谱以及单晶 X 射线衍射（SC-XRD）等技术对其进行了表征。计算得出的密度泛函理论（DFT）优化的分子几何形状与 SC-XRD 得到的构象相似。N-piperidinyl-o-sulfanilamide 和 N-indolinyl-o-sulfanilamide 的分子对接支持了邻磺酰胺能够与人类碳酸酐酶 II 和 IX 抑制剂（hCA II 和 IX；PDB 条目 4iwz 和 5fl4）结合的观点。对三种邻硝基磺酰胺{1-[(2-硝基苯基)磺酰基]吡咯烷，C10H12N2O4S，1，1-[(2-硝基苯基)磺酰基]哌啶、1-[（2-硝基苯基）磺酰基]吡咯烷，C10H12N2O4S，1；1-[（2-硝基苯基）磺酰基]哌啶，C11H14N2O4S，2；和 1-[（2-硝基苯基）磺酰基]-2,3-二氢-1H-吲哚，C14H12N2O4S，3}以及三种 N-环氨基邻磺酰苯胺[2-（吡咯烷-1-磺酰基）苯胺，C10H14N2O2S，4、2-（哌啶-1-磺酰基）苯胺，C11H16N2O2S，5 和 2-（2,3-二氢-1H-吲哚-1-磺酰基）苯胺，C14H14N2O2S，6]表明，氢键和 π-π 相互作用等力将分子连接在一起，并进一步表明，电荷转移可促进生物活性以及在哌啶基和苯基上形成生物相互作用的能力。

  DOI：

  10.1107/s2053229622010130
• 作为产物：
  描述：

  邻硝基苯磺酰氯 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 丙酮 为溶剂， 生成 1-(2-硝基苯基磺酰基)哌啶
  参考文献：
  名称：

  Acylating and arylsulfonylating ability of O-derivatives of isatin 3-oximes

  摘要：

  DOI：

  10.1007/s10593-005-0114-7

文献信息

• Metal-free synthesis of sulfonamides via iodine-catalyzed oxidative coupling of sulfonyl hydrazides and amines
  作者：Santosh Kumar Reddy Parumala、Rama Krishna Peddinti

  DOI：10.1016/j.tetlet.2016.02.009

  日期：2016.3

  A novel, rapid, and environmentally-friendly protocol for the synthesis of sulfonamides using iodine as catalyst under solvent-free conditions is described. This method involves the oxidative coupling of sulfonyl hydrazides and amines in the presence of catalytic amount of iodine using TBHP as oxidant. This protocol does not require purification techniques such as column chromatography and recrystalization

  描述了一种在无溶剂条件下使用碘作为催化剂合成磺酰胺的新颖，快速且环境友好的方案。该方法涉及在使用TBHP作为氧化剂的催化量碘存在下，磺酰肼和胺的氧化偶联。该方案不需要纯化技术，例如柱色谱法和重结晶法。
• <i>N</i>-Cycloamino substituent effects on the packing architecture of <i>ortho</i>-sulfanilamide molecular crystals and their <i>in silico</i> carbonic anhydrase II and IX inhibitory activities
  作者：Sherif O. Kolade、Josephat U. Izunobi、Allen T. Gordon、Eric C. Hosten、Idris A. Olasupo、Adeniyi S. Ogunlaja、Olayinka T. Asekun、Oluwole B. Familoni

  DOI：10.1107/s2053229622010130

  日期：2022.12.1

  In the search for new `sulfa drugs' with therapeutic properties, o-nitrosulfonamides and N-cycloamino-o-sulfanilamides were synthesized and characterized using techniques including ¹H NMR, ¹³C NMR and FT–IR spectroscopy, and single-crystal X-ray diffraction (SC-XRD). The calculated density functional theory (DFT)-optimized geometry of the molecules showed similar conformations to those obtained by SC-XRD. Molecular docking of N-piperidinyl-o-sulfanilamide and N-indolinyl-o-sulfanilamide supports the notion that o-sulfanilamides are able to bind to human carbonic anhydrase II and IX inhibitors (hCA II and IX; PDB entries 4iwz and 5fl4). Hirshfeld surface analyses and DFT studies of three o-nitrosulfonamides 1-[(2-nitrophenyl)sulfonyl]pyrrolidine, C₁₀H₁₂N₂O₄S, 1, 1-[(2-nitrophenyl)sulfonyl]piperidine, C₁₁H₁₄N₂O₄S, 2, and 1-[(2-nitrophenyl)sulfonyl]-2,3-dihydro-1H-indole, C₁₄H₁₂N₂O₄S, 3} and three N-cycloamino-o-sulfanilamides [2-(pyrrolidine-1-sulfonyl)aniline, C₁₀H₁₄N₂O₂S, 4, 2-(piperidine-1-sulfonyl)aniline, C₁₁H₁₆N₂O₂S, 5, and 2-(2,3-dihydro-1H-indole-1-sulfonyl)aniline, C₁₄H₁₄N₂O₂S, 6] suggested that forces such as hydrogen bonding and π–π interactions hold molecules together and further showed that charge transfer could promote bioactivity and the ability to form biological interactions at the piperidinyl and phenyl moieties.

  为了寻找具有治疗特性的新型 "磺胺药物"，我们合成了邻硝基磺酰胺和 N-环氨基邻磺酰苯胺，并利用 1H NMR、13C NMR 和 FT-IR 光谱以及单晶 X 射线衍射（SC-XRD）等技术对其进行了表征。计算得出的密度泛函理论（DFT）优化的分子几何形状与 SC-XRD 得到的构象相似。N-piperidinyl-o-sulfanilamide 和 N-indolinyl-o-sulfanilamide 的分子对接支持了邻磺酰胺能够与人类碳酸酐酶 II 和 IX 抑制剂（hCA II 和 IX；PDB 条目 4iwz 和 5fl4）结合的观点。对三种邻硝基磺酰胺1-[(2-硝基苯基)磺酰基]吡咯烷，C10H12N2O4S，1，1-[(2-硝基苯基)磺酰基]哌啶、1-[（2-硝基苯基）磺酰基]吡咯烷，C10H12N2O4S，1；1-[（2-硝基苯基）磺酰基]哌啶，C11H14N2O4S，2；和 1-[（2-硝基苯基）磺酰基]-2,3-二氢-1H-吲哚，C14H12N2O4S，3}以及三种 N-环氨基邻磺酰苯胺[2-（吡咯烷-1-磺酰基）苯胺，C10H14N2O2S，4、2-（哌啶-1-磺酰基）苯胺，C11H16N2O2S，5 和 2-（2,3-二氢-1H-吲哚-1-磺酰基）苯胺，C14H14N2O2S，6]表明，氢键和 π-π 相互作用等力将分子连接在一起，并进一步表明，电荷转移可促进生物活性以及在哌啶基和苯基上形成生物相互作用的能力。
• Acylating and arylsulfonylating ability of O-derivatives of isatin 3-oximes
  作者：A. P. Stankevicius、P. B. Terentiev、L. N. Janushene、A. B. Savickas

  DOI：10.1007/s10593-005-0114-7

  日期：2005.1
• Synthesis, crystal structure and <i>in-silico</i> 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.
• Reactions of N- and C-alkenylanilines: X. Synthesis of 2-vinyldihydroindoles from 4-methyl-2-(pent-3-en-2-yl)aniline
  作者：G. G. Mazgarova、A. M. Absalyamova、R. R. Gataullin

  DOI：10.1134/s1070428012090096

  日期：2012.9

  2-(1-Iodoethyl)-3,5-dimethyl-1-(4-methylphenylsulfonyl)-2,3-dihydro-1H-indole reacted with pyridine, piperidine, N-alkylpiperidines, and dimethylformamide to give dehydrohalogenation and halogen substitution products whose ratio depended on the reagent structure. Heating of 2-(1-iodoethyl)-3,5-dimethyl-1-methylsulfonyl-2,3-dihydro-1H-indole with piperidine resulted in the formation of only dehydroiodination products.