(4-氨基苯磺酰基氨基)-乙酸 | 5616-30-8

• 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-氨基苯磺酰基氨基)-乙酸
• 中文别名: |(4-氨基苯磺酰基氨基)-乙酸
• 英文名称: 2-(4-aminobenzenesulfonylamino)ethanoic acid
• 英文别名: ((4-aminophenyl)sulfonyl)glycine；N-sulfanilyl-glycine；N-Sulfanilyl-glycin；N-p-Aminobenzolsulfonylglycin；(4-Amino-benzenesulfonylamino)-acetic acid；2-[(4-aminophenyl)sulfonylamino]acetic acid
• CAS: 5616-30-8
• 化学式: C₈H₁₀N₂O₄S
• 分子量: 230.244
• InChiKey: BPJUMYMTQYMSFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  118
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 海关编码：
  2935009090

反应信息

• 作为反应物：
  描述：

  (4-氨基苯磺酰基氨基)-乙酸 以 乙二醇 为溶剂， 以34%的产率得到1,4-bis((4-aminophenyl)sulfonyl)piperazine-2,5-dione
  参考文献：
  名称：

  Development of Piperazinediones as dual inhibitor for treatment of Alzheimer's disease

  摘要：

  Novel multifunctional 3,6-Diphenyl-1,4-bis(phenylsulfonyl)piperazine-2,5-dione derivatives were designed and synthesized for the treatment of Alzheimer's disease (AD). The designed scaffold has blood brain barrier penetrating ability, acetylcholinesterase (AChE) and matrix metalloproteinase-2 (MMP-2) inhibition potential. Compounds 52 and 46 showed very significant inhibition against AChE, IC50 = 32.45 +/- 0.044, 28.65 +/- 0.029, BuChE, IC50 = 157.95 +/- 0.264, 160.58 +/- 0.082 and MMP-2, IC50 = 36.83 +/- 0.015, 19.57 +/- 0.005 (nM). In the enzyme kinetics study, lead molecule 46 showed noncompetitive inhibition of AChE with K-i = 7 nM and competitive inhibition of MMP-2 with K-i = 20 nM. Compounds 52 and 46 inhibited AChE-induced A beta aggregation at 20 mu M. The compounds also exhibited in-vitro antioxidant potential in DPPH assay. Further, compound 46 was found to be a promising neuroprotective agent in MC65 cells. Lead molecule 46 significantly enhanced working memory in scopolamine induced amnesia animal model at dose of 5 mg/kg dose. The mitochondrial membrane potential was restored in animals when treated with compounds 52 and 46. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.02.078
• 作为产物：
  描述：

  对乙酰胺基苯磺酰氯 在 盐酸 、 sodium hydroxide 作用下， 生成 (4-氨基苯磺酰基氨基)-乙酸
  参考文献：
  名称：

  Organic Compounds in Chemotherapy. I. Derivatives of Sulfanilamide

  摘要：

  DOI：

  10.1021/ja01872a020

文献信息

• From a MMP2/CK2 multitarget approach to the identification of potent and selective MMP13 inhibitors
  作者：Miryam Pastor、José María Zapico、Claire Coderch、Maciej Maslyk、Rostyslav Panchuk、Beatriz de Pascual-Teresa、Ana Ramos

  DOI：10.1039/c8ob02990c

  日期：——

  MMP2/CK2 dual targeting inhibitors. We have followed a rational drug design approach based on our experience in the selective inhibition of these two enzymes. We have successfully obtained highly active MMP2 (10, IC50 = 70 nM; 11, IC50 = 100 nM) and CK2 (16a, IC50 = 500 nM) inhibitors. However, structural fine tuning of these small molecules to simultaneously target both enzymes turned out to be an unattainable

  在本文中，我们描述了我们在寻找MMP2 / CK2双重靶向抑制剂方面的努力。我们根据选择性抑制这两种酶的经验，采用了合理的药物设计方法。我们已经成功获得了高活性的MMP2（10，IC 50 = 70 nM; 11，IC 50 = 100 nM）和CK2（16a，IC 50 = 500 nM）抑制剂。然而，对这些小分子进行结构微调以同时靶向两种酶被证明是无法实现的目标。出乎意料的是，我们很幸运地发现了新的选择性MMP13抑制剂（10，IC 50 = 3.7 nM和11，IC 50= 5.6 nM）的TBB衍生支架。这些化合物构成了进一步优化的有趣起点。
• Broad-Specificity Immunoassays for Sulfonamide Detection:  Immunochemical Strategy for Generic Antibodies and Competitors
  作者：Milan Franek、Iva Diblikova、Ivo Cernoch、Maria Vass、Karel Hruska

  DOI：10.1021/ac0514422

  日期：2006.3.1

  Development of antibodies with broad specificity recognition for sulfonamide drugs was found to be surprisingly difficult when conventional immunochemical strategies were applied to hapten design. To improve the cross-reactivity pattern of antibodies for the family of sulfonamide drugs, a novel strategy based on the single-ring (fragment-derived) hapten moieties with different spacer substituent lengths was employed for the preparation of immunogens, coating conjugates, and enzyme competitors. The rabbit antibodies raised against a common (one-ring) p-aminobenzenesulfonamide hapten moiety (attached to a carrier protein through the N-1 position) in combination with a homologous hapten−peroxidase tracer allowed the detection of 15 sulfonamide species at the maximum residue limit level using direct ELISA. The two-ring 6-(4-aminobenzensulfonylamino)hexanoic hapten mimics, previously reported in the literature as a weak generic antigen, generated surprisingly superior immune responses in rabbits. The antibodies raised against this two-ring hapten were capable of detecting at least 19 and 17 sulfonamides in a direct ELISA system at the regulatory level with sensitivities corresponding to 20 and 50% binding inhibition, respectively. A negligible cross-reaction with N4 metabolites makes it possible to measure responses of parent sulfonamides in the presence of their metabolized forms. In skimmed milk, the highest limit of detection (LOD) for sulfacetamide defined as 20% inhibition was 65.2 μg·L-1 (IC20 value), whereas the additional 18 sulfonamides tested exhibited LODs in the range of 0.2−36.8 μg·L-1. This sensitivity allows simple multisulfonamide tests to be established for use in the laboratory or on site.

  开发具有广谱特异性识别磺胺类药物的抗体在应用传统免疫化学策略进行半抗原设计时发现异常困难。为了改善针对磺胺类药物家族的抗体交叉反应模式，采用了基于单环（片段衍生）半抗原母体与不同间隔取代长度的策略来制备免疫原、包被偶联物和酶竞争剂。针对常见（单环）对氨基苯磺酰胺半抗原母体（通过N-1位置连接载体蛋白）以及同源半抗原-过氧化物酶示踪剂，能够利用直接ELISA法检测到15种磺胺类品种在最大残留限量的水平。先前文献报道为弱泛抗原的双环6-（4-氨基苯磺酰氨基）己酸半抗原模拟物，在兔子中引发了显著更优越的免疫反应。针对此双环半抗原产生的抗体能够在一个直接ELISA体系中以对应20%和50%结合抑制的灵敏度分别检测至少19种和17种磺胺类药物。对N4代谢物几乎无交叉反应使得在存在其代谢形式的情况下能够测量母体磺胺类药物的反应。在脱脂牛奶中，以20%抑制定义的最高检测限（LOD），磺胺醋酰为65.2 μg·L-1（IC20值），而另外测试的18种磺胺类药物的LOD范围在0.2−36.8 μg·L-1。这种灵敏度允许在实验室或现场建立简单多磺胺检测。
• [EN] POLYMERIC HYPERBRANCHED CARRIER-LINKED PRODRUGS<br/>[FR] PROMÉDICAMENTS LIÉS À DES EXCIPIENTS POLYMÉRIQUES HYPERBRANCHÉS
  申请人：ASCENDIS PHARMA AS

  公开号：WO2013024048A1

  公开（公告）日：2013-02-21

  The present invention relates to water-soluble carrier-linked prodrugs of formula (I),wherein POL is a polymeric moiety,each Hyp is independently a hyperbranched moiety,each moiety SP is independently a spacer moiety, each L is independently a reversible prodrug linker moiety, m is 0 or 1, each n is independently an integer from 2 to 200 and each x is independently 0 or 1. It further relates to pharmaceutical compositions comprising said water- soluble carrier-linked prodrugs and methods of treatment.

  本发明涉及水溶性载体连接的前药，其化学式为（I），其中POL是聚合物基团，每个Hyp是独立的超支化基团，每个基团SP是独立的间隔基团，每个L是独立的可逆前药连接基团，m为0或1，每个n是独立的整数，范围从2到200，每个x是独立的0或1。此外，还涉及包含所述水溶性载体连接的前药的药物组合物和治疗方法。
• [EN] HIGH-LOADING WATER-SOLUBLE CARRIER-LINKED PRODRUGS<br/>[FR] PROMÉDICAMENTS LIÉS À DES EXCIPIENTS HYDROSOLUBLES DE FORTE CHARGE
  申请人：ASCENDIS PHARMA AS

  公开号：WO2013024047A1

  公开（公告）日：2013-02-21

  The present invention relates to water-soluble carrier-linked prodrugs of formula (I), wherein B, A and Hyp form the carrier, B is a branching core, each A is independently a poly(ethylene glycol)-based polymeric chain, each Hyp is independently a branched moiety, each SP is independently a spacer moiety, each L is independently a reversible prodrug linker moiety, each D is independendly a biologically active moiety, each x is independently 0 or 1, each m is independently an integer of from 2 to 64, n is an integer from 3 to 32; or the pharmaceutically acceptable salt thereof. It further relates to pharmaceutical compositions comprising said water-soluble carrier-linked prodrugs, their use asmedicament or diagnostic, and methods of treatment.

  本发明涉及水溶性载体连接的前药，其化学式为(I)，其中B、A和Hyp形成载体，B是一个分支核心，每个A独立地是一条聚乙二醇基聚合链，每个Hyp独立地是一个分支基团，每个SP独立地是一个间隔基团，每个L独立地是一个可逆前药连接基团，每个D独立地是一个生物活性基团，每个x独立地为0或1，每个m独立地是从2到64的整数，n是从3到32的整数；或其药学上可接受的盐。进一步涉及包括所述水溶性载体连接的前药的药物组合物，其用作药物或诊断，以及治疗方法。
• [EN] RELEASABLE CONJUGATES<br/>[FR] CONJUGUÉS LIBÉRABLES
  申请人：QUIAPEG PHARMACEUTICALS AB

  公开号：WO2018163131A1

  公开（公告）日：2018-09-13

  The present application provides compounds of Formula (B), or pharmaceutically acceptable salts thereof, wherein D is a residue of a biologically active drug, which underdo hydrolysis under physiological conditions to release the biologically active drug and which are useful in the treatment of disorders that could be beneficially treated with the drug.

  本申请提供了化合物的公式（B），或其药用盐，其中D是生物活性药物的残留物，在生理条件下经过水解释放出生物活性药物，并且对可能受益于该药物治疗的疾病具有用处。