4-氨基-N-异丁基苯磺酰胺 | 53668-36-3

• 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: 4-氨基-N-异丁基苯磺酰胺
• 英文名称: 4-amino-N-isobutylbenzenesulfonamide
• 英文别名: 4-amino-N-(2-methylpropyl)benzenesulfonamide
• CAS: 53668-36-3
• 化学式: C₁₀H₁₆N₂O₂S
• mdl: MFCD03753719
• 分子量: 228.315
• InChiKey: QOKGSVHQDFFSRS-UHFFFAOYSA-N

物化性质

• 溶解度：
  >34.2 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  80.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2935009090

反应信息

• 作为反应物：
  描述：

  4-氨基-N-异丁基苯磺酰胺 在 苄基三乙基氯化铵 、 potassium carbonate 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 4-氨基-N-[(2R, 3S)-3-氨基-2-羟基-4-苯丁基]-N-异丁基苯磺酰胺
  参考文献：
  名称：

  [EN] PROCESS FOR THE PREPARATION OF SULFONAMIDES USEFUL AS RETROVIRAL PROTEASE INHIBITORS
  [FR] PROCÉDÉ DE PRÉPARATION DE SULFONAMIDES UTILES EN TANT QU'INHIBITEURS DE PROTÉASE RÉTROVIRAUX

  摘要：

  本发明涉及一种用于制备作为逆转录病毒蛋白酶抑制剂有用的磺胺类化合物的方法。

  公开号：

  WO2013011485A1
• 作为产物：
  描述：

  N-异丁基-2-硝基苯磺酰胺 在 盐酸 、 tin 作用下， 以 乙醇 、 水 为溶剂， 以86%的产率得到4-氨基-N-异丁基苯磺酰胺
  参考文献：
  名称：

  Potent and selective N-(4-sulfamoylphenyl)thiourea-based GPR55 agonists

  摘要：

  To date, many known G protein-coupled receptor 55 (GPR55) ligands are those identified among the cannabinoids. In order to further study the function of GPR55, new potent and selective ligands are needed. In this study, we utilized the screening results from PubChem bioassay AID 1961 which reports the results of Image-based HIS for Selective Agonists of GPR55. Three compounds, CID1792579, CID1252842 and CID1011163, were further evaluated and used as a starting point to create a series of nanomolar potency GPR55 agonists with N-(4-sulfamoylphenyl)thiourea scaffold. The GPR55 activity of the compounds were screened by using a commercial beta-arrestin PathHunter assay and the potential compounds were further evaluated by using a recombinant HEK cell line exhibiting GPR55-mediated effects on calcium signalling. The designed compounds were not active when tested against various endocannabinoid targets (CB1R, CB2R, FAAH, MGL, ABHD6 and ABHD12), indicating compounds' selectivity for the GPR55. Finally, structure activity relationships of these compounds were explored. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.10.050

文献信息

• Pyridoxal-5-phosphate derivatives as HIV integrase inhibitors
  申请人：Pharmacor Inc.

  公开号：US06638921B1

  公开（公告）日：2003-10-28

  A compound of formula I and pharmaceutically acceptable derivatives thereof Cx, R1 and R2 being as defined in the disclosure may be used to inhibit the activity of HIV integrase.

  化合物的化学式为I，及其在药学上可接受的衍生物Cx，其中R1和R2的定义如披露中所述，可用于抑制HIV整合酶的活性。
• Cyclin dependent kinase inhibiting purine derivatives
  申请人：——

  公开号：US20040110775A1

  公开（公告）日：2004-06-10

  The present invention relates to a series of CDK-inhibiting purine derivatives of structural formula (I), or a pharmaceutically acceptable salt and/or prodrug form thereof, wherein: X is O, S or CHR X where R X is H or C 1-14 alkyl; D is NZ 1 Z 2 where Z 1 is selected from H, C 1-4 alkyl, C 1-4 hydroxyalkyl, an unsubstituted or substituted aryl or heteroaryl, and an unsubstituted or substituted aralkyl or heteroaralkyl group, and Z 2 is selected from an unsubstituted or substituted aryl or heteroaryl, and an unsubstituted or substituted aralkyl or heteroaralkyl group; A is selected from H, C 1-4 alkyl, C 1-4 alkoxy, hydroxy, CH 2 (CH 2 ) n OH (n=1-4), and NR a1 R a2 where R a1 and Ra 2 are each independently H or C 1-4 alkyl; B is selected from H, halo, C 1-4 alkyl, C 1-4 alkoxy, CF 3 , an optionally substituted aryl or an optionally substituted aralkyl, and a hydroxy group that may undergo a C═O tautomeric rearrangement; and Y comprises an unsubstituted or substituted 4- to 8-membered carbocyclic or heterocyclic ring, optionally forming part of a larger fused ring structure, or consists of an optionally substituted linear or branched hydrocarbon chain. These purine derivatives are potential chemotherapeutic agents and, accordingly, the present invention also relates to the use of these compounds in the treatment of tumours or other cell proliferation disorders and pharmaceutical compositions comprising these compounds.

  本发明涉及一系列CDK抑制嘌呤衍生物，其结构式（I），或其药学上可接受的盐和/或前药形式，其中：X为O、S或CHRX，其中RX为H或C1-14烷基；D为NZ1Z2，其中Z1选择自H、C1-4烷基、C1-4羟基烷基、未取代或取代的芳基或杂芳基，以及未取代或取代的芳基或杂芳基基团，Z2选择自未取代或取代的芳基或杂芳基，以及未取代或取代的芳基或杂芳基基团；A选择自H、C1-4烷基、C1-4烷氧基、羟基、CH2(CH2)nOH（n=1-4），和NRa1Ra2，其中Ra1和Ra2各自独立地为H或C1-4烷基；B选择自H、卤素、C1-4烷基、C1-4烷氧基、CF3、一个可选择取代的芳基或可选择取代的芳基基团，以及可能经历C=O互变异构重排的羟基；Y包括未取代或取代的4-至8-成员碳环或杂环，可选地构成更大的融合环结构的一部分，或由一个可选择取代的线性或支链烃链组成。这些嘌呤衍生物是潜在的化疗药物，因此，本发明还涉及将这些化合物用于治疗肿瘤或其他细胞增殖障碍的用途，以及包含这些化合物的药物组合物。
• A base labile handle for solid phase organic chemistry
  作者：Carlos García-Echeverría

  DOI：10.1016/s0040-4039(97)10386-0

  日期：1997.12

  Several arylsulfonamides have been synthesised on solid phase using a new base labile handle. Cleavage from the solid support is accomplished by oxidation of the sulfide to the sulfone, followed by β-elimination in base media.

  使用新的碱不稳定的手已在固相上合成了几种芳基磺酰胺。通过将硫化物氧化成砜，然后在碱性介质中进行β-消除，可以完成从固相载体上的裂解。
• Mechanochemical Conversion of Aromatic Amines to Aryl Trifluoromethyl Ethers
  作者：Michał Jakubczyk、Satenik Mkrtchyan、Mohanad Shkoor、Suneel Lanka、Šimon Budzák、Miroslav Iliaš、Marek Skoršepa、Viktor O. Iaroshenko

  DOI：10.1021/jacs.2c02611

  日期：2022.6.15

  Increased interest in the trifluoromethoxy group in organic synthesis and medicinal chemistry has induced a demand for new, selective, general, and faster methods applicable to natural products and highly functionalized compounds at a later stage of hit-to-lead campaigns. Applying pyrylium tetrafluoroborate, we have developed a mechanochemical protocol to selectively substitute the aromatic amino group

  在有机合成和药物化学中对三氟甲氧基的兴趣日益增加，这引发了对适用于天然产物和高度功能化化合物的新的、选择性的、通用的和更快的方法的需求，这些方法适用于“命中率”活动的后期阶段。应用 pyrylium tetrafluoroborate，我们开发了一种机械化学方案，以选择性地用 OCF 3官能团取代芳族氨基。我们方法的范围包括 31 个环取代苯胺的例子，包括酰胺和磺胺。以优异的产率获得了预期的 S N Ar 产品。所提出的简洁方法为制药行业开辟了通往新化学空间的途径。
• Organic nonlinear optical materials
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0644453A1

  公开（公告）日：1995-03-22

  Organic nonlinear optical materials that have light absorption in the crystal at wavelengths shorter than 390 nm, that have good crystallinity and processability, that have a non-centrosymmetry molecular arrangement and that hence are suitable for use in wavelength conversion devices comprises compounds having the formula I: where    R¹, R² and R³ which may be the same or different represent a hydrogen atom, an alkyl group, an aryl group or a heterocyclic group;    R⁴ is a hydrogen atom, an alkyl group, an aryl group, a heterocyclic group or an electron withdrawing group;    R⁵ which may be the same or different represent a hydrogen atom, an alkyl group, an aryl group, a heterocyclic group or an electron donating group;    m is an integer of 1 to 4;    when m is 2 or more, two or more R⁵s may bind together to form a ring;    provided that R³ is not a methyl group when R¹, R², R⁴ and R⁵ are all hydrogen atoms.

  有机非线性光学材料在波长短于 390 纳米的晶体中具有光吸收特性，具有良好的结晶性和加工性，具有非中心对称的分子排列，因此适用于波长转换装置，包括具有式 I 的化合物： 式中 可以相同或不同的 R¹、R² 和 R³ 代表氢原子、烷基、芳基或杂环基团； R⁴ 是氢原子、烷基、芳基、杂环基团或退电子基团； 可以相同或不同的 R⁵ 代表氢原子、烷基、芳基、杂环基团或电子捐赠基团； m 是 1 至 4 的整数； 当 m 为 2 或 2 以上时，两个或两个以上的 R⁵ 可结合在一起形成一个环； 当 R¹、R²、R⁴ 和 R⁵ 都是氢原子时，R³ 不是甲基。