N-(2-aminoethyl)-4-tert-butylbenzenesulfonamide

• 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: N-(2-aminoethyl)-4-tert-butylbenzenesulfonamide
• 英文别名: N-(2-amino-ethyl)-4-t-butyl-benzenesulfonamide
• 化学式: C₁₂H₂₀N₂O₂S
• mdl: MFCD10024778
• 分子量: 256.369
• InChiKey: QUPJTOLVKZCCKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  80.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-氯-4-氨基-6,7-二甲氧基喹唑啉 、 N-(2-aminoethyl)-4-tert-butylbenzenesulfonamide 以 正丁醇 为溶剂， 生成 N-[2-(4-amino-6,7-dimethoxy-quinazolin-2-ylamino)-ethyl]-4-tert-butyl-benzene sulfonamide
  参考文献：
  名称：

  Pharmacological Exploitation of the α1-Adrenoreceptor Antagonist Doxazosin to Develop a Novel Class of Antitumor Agents That Block Intracellular Protein Kinase B/Akt Activation

  摘要：

  The alpha1-adrenoreceptor antagonist doxazosin induces apoptosis in malignant cells with moderate potency via an alpha1-adrenoreceptor-independent mechanism. Here, we demonstrate that the ability of doxazosin to induce apoptosis in PC-3 prostate cancer cells was, in part, attributable to the inhibition of protein kinase B (PKB)/Akt activation. The separation of the effect of doxazosin on apoptosis from its original pharmacological activity provides molecular underpinnings to develop novel antitumor agents. Replacement of the (2,3-dihydro-benzo[1,4]dioxane)-carbonyl moiety of doxazosin with aryl-sulfonyl functions dramatically improves the potency in facilitating Akt deactivation and inducing apoptosis. The optimal compounds, 33 and 44, were effective in apoptosis induction at low micromolar concentrations irrespective of androgen dependency and p53 functional status. Both agents were active in suppressing the growth of a panel of 60 cancer-cell lines with IC50 values of 2.2 and 1.5 muM, respectively. Together, these in vitro efficacy data suggest the translational potential of these agents in prostate cancer treatment.

  DOI：

  10.1021/jm049752k
• 作为产物：
  描述：

  对叔丁基苯磺酰氯 、 乙二胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-(2-aminoethyl)-4-tert-butylbenzenesulfonamide
  参考文献：
  名称：

  含氧缩醛和嘧啶的新型磺胺类药物的合成、抗菌活性及作用机制

  摘要：

  细菌性叶枯病（BLB）和细菌性叶斑病（BLS）是由米黄单胞菌引起的两种严重的细菌性病害。oryzae ( Xoo ) 和Xanthomonas oryzae pv. oryzicola ( Xoc )，分别。然而，由于耐药性的发展，传统农药对这些疾病的控制仍然具有挑战性。我们旨在解决这个悬而未决的问题，并开发了一系列新型嘧啶磺酰胺衍生物。在结构上，标题化合物带有一个独特的氧缩醛基团，具有经证实的免疫激活作用。基于 3D-QSAR 模型设计的化合物E35在体外被证明是最佳的对Xoo和Xoc的活性，EC 50值分别为 26.7 和 30.8 mg/L，高于阳性对照双甲基噻唑（29.9 和 32.7 mg/L）和噻二唑铜（30.5 和 36.4 mg/L）。在预防水平上，生物活性试验表明，化合物E35对BLS的保护活性（43.7%）优于噻二唑铜（32.1%）。防御酶和蛋白质组学结果表明，化合物E

  DOI：

  10.1021/acs.jafc.2c02099

文献信息

• Design of base metal extractants. Part 1. Inter-ligand hydrogen bonding in the assembly of pseudo-macrocyclic bis(aminosulfonamidato)M(ii) complexes
  作者：Clare Squires、Christopher W. Baxter、John Campbell、Leonard F. Lindoy、Hamish McNab、Andrew Parkin、Simon Parsons、Peter A. Tasker、Gang Wei、David J. White

  DOI：10.1039/b515650p

  日期：——

  Monosulfonyl derivatives of simple 1,2- and 1,3-diamines (R2HN–R–NHSO2R1 = L) have been shown to be easily deprotonated to give neutral 2 : 1 complexes, [M(L − H)2], with Co(II), Ni(II), Cu(II) or Zn(II). The Ni(II) and Cu(II) complexes with deprotonated N-tosyl-1,2-diaminoethane have a planar N42− donor set and a 14-membered pseudo-macrocyclic structure based on head-to-tail SO⋯H–N(amine) bonding between the two bidentate ligands. In the related tetrahedral Zn(II) complex the ends of the mutually perpendicular bidentate N2− units are too far apart to form a cyclic H-bonded system. X-Ray structure determinations on five free ligands provide evidence for extensive inter-molecular H-bonding, which in the case of N-tosyl-1,3-diaminopropane and its N′-tert-butyl derivative involves formation of dimeric 16-membered pseudo-macrocycles. Despite favourable inter-ligand H-bonding in the neutral 2 : 1 complexes, these ligands are relatively weak extractants, showing >50% loading of Cu(II) in “pH-swing” equilibria, 2 L(org) + M2+ = [M(L − H)2](org) + 2 H+, only when the pH of the aqueous phase is raised above 4.

  研究表明，简单的 1,2- 和 1,3- 二胺（R2HN-R-NHSO2R1 = L）的单磺酰衍生物很容易去质子化，从而与 Co(II)、Ni(II)、Cu(II) 或 Zn(II) 生成 2 : 1 的中性络合物 [M(L-H)2]。含有去质子化 N-对甲基苯磺酰-1,2-二氨基乙烷的 Ni(II) 和 Cu(II) 复合物具有平面 N42 供体组和 14 元伪大环结构，该结构基于两个双齿配体之间头对尾的 SO⋯H-N（胺）键。在相关的四面体 Zn(II) 复合物中，相互垂直的双齿 N2- 单元两端相距太远，无法形成环状 H 键体系。对五种游离配体的 X 射线结构测定证明了分子间广泛的 H 键作用，在 N-对甲苯磺酸-1,3-二氨基丙烷及其 N′-叔丁基衍生物中，这种作用涉及形成二聚 16 元伪大环。尽管在中性 2 : 1 复合物中存在有利的配体间氢键，但这些配体是相对较弱的萃取剂，只有当水相的 pH 值升高到 4 以上时，才会在 "pH 波动 "平衡（2 L(org) + M2+ = [M(L - H)2](org) + 2 H+）中显示出大于 50% 的 Cu(II) 负载。
• NOVEL ANTITUMOR AGENTS AND METHODS OF THEIR USE
  申请人：Chen Ching-Shih

  公开号：US20090048265A1

  公开（公告）日：2009-02-19

  Antitumor compounds based on the α1-adrenoceptor antagonist, doxazosin, as well as compositions and methods of use. The disclosed compounds induce apoptosis in cancer cells.

  基于α1-肾上腺素能受体拮抗剂多沙唑嗪的抗肿瘤化合物，以及其组合物和使用方法。所披露的化合物能诱导癌细胞凋亡。
• Antitumor agents and methods of their use
  申请人：Chen Ching-Shih

  公开号：US08377948B2

  公开（公告）日：2013-02-19

  Antitumor compounds based on the α1-adrenoceptor antagonist, doxazosin, as well as compositions and methods of use. The disclosed compounds induce apoptosis in cancer cells.

  抗肿瘤化合物基于α1-肾上腺素受体拮抗剂多沙唑嗪，以及其组合物和使用方法。所披露的化合物能够诱导癌细胞凋亡。
• Design, synthesis and antibacterial activity evaluation of ebselen derivatives in NDM-1 producing bacteria
  作者：Wanli Meng、Chenyu Liu、Guangxin Wu、Zhongyue Bai、Zhihao Wang、Sheng Chen、Shengbiao Wan、Wandong Liu

  DOI：10.1039/d4md00031e

  日期：——

  restore the efficacy of meropenem (Mem) against NDM-1 producing strains. In this study, 22 compounds were designed and synthesized, which restored the Mem susceptibility of NDM-1-expressing Escherichia coli. and its minimum inhibitory concentration (MIC) was reduced by 2–16 times. Representative compound A4 showed significant synergistic antibacterial activity against NDM-1-producing carbapenem-resistant

  新德里-β-内酰胺酶-1 (NDM-1) 是一种金属-β-内酰胺酶。表达NDM-1的细菌可以通过质粒转移在全球范围内迅速传播，这极大地损害了碳青霉烯类药物的临床疗效。 NDM-1抑制剂的研究引起了广泛关注。然而，目前尚无临床可用的NDM-1抑制剂。我们的研究小组报道了1,2-benzisoselenazol-3(2 H )-one衍生物作为共价NDM-1抑制剂可以恢复美罗培南（Mem）对NDM-1产生菌株的功效。在这项研究中，设计并合成了22种化合物，恢复了表达NDM-1的大肠杆菌的Mem敏感性。其最低抑菌浓度（MIC）降低2~16倍。代表性化合物A4对产生 NDM-1 的碳青霉烯类耐药肠杆菌 (CRE) 分离株表现出显着的协同抗菌活性。体外NDM-1酶抑制活性测试显示IC 50为1.26±0.37 μM，具有较低的细胞毒性。与美罗培南合用时，表现出良好的联合抗菌活性。电喷雾电离质谱 (ESI-MS)
• pH-Regulated transfer hydrogenation of quinoxalines with a Cp*Ir–diamine catalyst in aqueous media
  作者：Jing Tan、Weijun Tang、Yawei Sun、Zhen Jiang、Fei Chen、Lijin Xu、Qinghua Fan、Jianliang Xiao

  DOI：10.1016/j.tet.2011.06.067

  日期：2011.8

  The combination of [Cp*IrCl2](2) with N-(2-aminoethyl)-4-(trifluoromethyl)benzenesulfonamide constitutes an efficient catalyst for selective transfer hydrogenation of a variety of quinoxalines in water with HCOONa as the hydrogen source, affording the corresponding tetrahydroquinoxalines in good to excellent yields. The catalyst is air-stable, and the reduction could be performed without nitrogen protection. The aqueous phase reduction is shown to be highly pH-dependent, with acidic pH leading to better results. There exits a pH window for optimum rate, and the use of HOAc/NaOAc buffer solution is essential for maintaining a stable pH during the reaction. (C) 2011 Elsevier Ltd. All rights reserved.