4-氨基-3-巯基苯甲酸盐酸盐 | 1571-66-0

• 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-3-巯基苯甲酸盐酸盐
• 中文别名: 4-氨基-3-疏基苯甲酸盐酸盐
• 英文名称: 4-amino-3-mercaptobenzoic acid hydrochloride
• 英文别名: 4-amino-3-sulfanylbenzoic acid;hydrochloride
• CAS: 1571-66-0
• 化学式: C₇H₇NO₂S*ClH
• mdl: MFCD14584982
• 分子量: 205.665
• InChiKey: JDKUQNGATAJKNQ-UHFFFAOYSA-N

物化性质

• 熔点：
  288.5-290.0 °C

计算性质

• 辛醇/水分配系数(LogP)：
  0.74
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-氨基-3-巯基苯甲酸盐酸盐 在 吡啶 、 盐酸 、 sodium hydroxide 、 氯化亚砜 、 氢溴酸 、 sodium hydride 、 potassium carbonate 、 苯甲醚 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基乙酰胺 、 水 、 甲苯 为溶剂， 反应 91.5h， 生成 N-[[4-[(2,4-diaminopteridin-6-yl)methyl]-3,4-dihydro-2H-1,4-benzothiazin-7-yl]-carbonyl]-L-homoglutamic acid
  参考文献：
  名称：

  Antirheumatic Agents:  Novel Methotrexate Derivatives Bearing a Benzoxazine or Benzothiazine Moiety

  摘要：

  Novel methotrexate (MTX) derivatives bearing dihydro-2H-1,4-benzothiazine or dihydro-2H,1,4-benzoxazine were synthesized and tested for in vitro antiproliferative activities against human synovial cells (hSC) and human peripheral blood mononuclear cells (hPBMC) obtained from patients with rheumatoid arthritis and healthy volunteers, respectively. In vivo antiarthritic activities of these derivatives were also evaluated in a rat adjuvant arthritis model. N-[[4-[(2,4-Diaminopteridin-6-yl)methyl]-3,4-dihydro-2H-1,4-benzothiazin-7-yl]carbonyl]-L-glutamic acid (3c) exhibited more potent antiproliferative activities in hSC and hPBMC than MTX in vitro, Antiproliferative activities of N-[[4-[(2,4-diaminopteridin-6-yl)methyl]-3,4-dihydro-2H-1,4-benzoxazin-7-yl]carbonyl]-L-homoglutamic acid (3b) and N-[[4-[(2,4-diaminopteridin-6-yl)methyl]-3,4-dihydro-2H-1,4-benzothiazin-7-yl]carbonyl]-L-homoglutamic acid (3d) (MX-68) were comparable to that of MTX in these in vitro assays. Compounds 3b,d (MX-68) significantly suppressed progression of the adjuvant arthritis in a dose-dependent manner ranging from 0.5 to 2.5 mg/kg (po). In addition, 3d (MX-68) completely suppressed this progression at the dose of 2.5 mg/kg (po). Importantly, 3d (MX-68) having benzothiazine and homoglutamate, as expected, did not undergo polyglutamation, a process which may be responsible for the associated side effects of MTX. These results suggest that 3d (MX-68) is a potent and safe candidate antirheumatic agent, absent of the side effects of MTX.

  DOI：

  10.1021/jm9605288
• 作为产物：
  描述：

  2-氨基苯并噻唑-6-甲酸 在 potassium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 4.25h， 以Ca. 1.75 g的产率得到4-氨基-3-巯基苯甲酸盐酸盐
  参考文献：
  名称：

  可调杂芳族砜增强细胞内半胱氨酸分析

  摘要：

  杂芳族砜通过亲核芳香取代与半胱氨酸反应，为半胱氨酸缀合提供机械选择性和不可逆支架。在这里，我们评估了具有不同氧化态、杂原子取代和一系列给电子和吸电子取代基的杂芳族硫化物库。与传统的半胱氨酸偶联试剂相比，选择取代对反应性和稳定性产生了深远的影响，将反应速率提高了 > 3 个数量级。研究结果建立了一系列可合成的可跨多个可调中心可调的亲电支架。新的亲电子试剂及其相应的炔烃偶联物直接在培养的细胞中进行分析，在几分钟内以亚毫摩尔浓度实现硫醇饱和。将脱硫生物素功能化探针直接添加到培养细胞中简化了富集和洗脱，从而能够在标准分析时间的一小部分内通过质谱发现在其天然细胞环境中标记的 >3000 个反应性和/或可接近的硫醇。令人惊讶的是，在重复实验中，只有 1/2 的注释半胱氨酸被碘乙酰胺-脱硫生物素和甲基磺酰基苯并噻唑-脱硫生物素鉴定，证明了质谱分析的互补检测。与现有的半胱氨酸烷基化试剂相比，这些探针具有优

  DOI：

  10.1021/jacs.9b08831

文献信息

• Design, synthesis and evaluation of benzothiazole derivatives as multifunctional agents
  作者：Ernestine Nicaise Djuidje、Sabrina Sciabica、Raissa Buzzi、Valeria Dissette、Jan Balzarini、Sandra Liekens、Elena Serra、Elisa Andreotti、Stefano Manfredini、Silvia Vertuani、Anna Baldisserotto

  DOI：10.1016/j.bioorg.2020.103960

  日期：2020.8

  aetiology of various multifactorial diseases; on the other hand, the development of multifunctional compounds is a recognized strategy for the control of complex diseases. To this end, a series of benzothiazole derivatives was synthesized and evaluated for their multifunctional effectiveness as antioxidant, sunscreen (filter), antifungal and antiproliferative agents. Compounds were easily synthesized

  氧化应激是多种多因素疾病的产物或病因。另一方面，开发多功能化合物是控制复杂疾病的公认策略。为此，合成了一系列苯并噻唑衍生物并评估了其作为抗氧化剂，防晒霜（过滤剂），抗真菌剂和抗增殖剂的多功能功效。通过2-氨基硫酚与不同的苯甲醛之间的缩合反应可轻松合成化合物。SAR研究，特别是在苯并噻唑的2位和6位上，对4g和4k的鉴定为多功能药物设计中非常有趣的潜在化合物。特别是化合物4g是在HEK 293细胞中表达的hERG钾通道的最佳阻滞剂，具有60.32％的抑制作用，IC 50  = 4.79μM。
• AN IMPROVED PREPARATION OF 4-AMINO-3-MERCAPTOBENZOIC ACID
  作者：Robert C. Lang、Craig M. Williams、Mary J. Garson

  DOI：10.1080/00304940309355864

  日期：2003.10

  10. K. Undheim and B. P. Nilsen, Acta Chem. Scand. B, 29,503 (1975). 11. S. K. Ghorai, Ph.D Thesis, Z.Z.T. Kharagpur, (2001). 12. B. M. Choudary, M. L. Kantam, B. Bharathi and C. V. Reddy, Synlett, 1203 (1998). 13 N. K. Hamer, J. Chem. SOC. Perkin I, 1285 (1979). 14. G. B. Payne, J. Org. Chem., 25,275 (1960). 15. K. L. Reed, J. T. Gupton and T. L. Solarz, Synth. Commun., 19,3579 (1989). 16. J. Katsuhara

  10. K. Undheim 和 BP Nilsen，Acta Chem。扫描。B, 29,503 (1975)。11. SK Ghorai，博士论文，ZZT Kharagpur，（2001 年）。12. BM Choudary, ML Kantam, B. Bharathi 和 CV Reddy, Synlett, 1203 (1998)。13 NK Hamer, J. Chem. SOC。珀金一世，1285 (1979)。14. GB Payne, J. Org. 化学，25,275 (1960)。15. KL Reed、JT Gupton 和 TL Solarz、Synth。公社，19,3579 (1989)。16. J. Katsuhara, J. Org. 化学，32,797 (1967)。17. TS Straub, Tetrahedron Lett., 36,663 (1995)。18
• Preparation of aromatic heterocyclic polymers
  申请人：THE DOW CHEMICAL COMPANY

  公开号：EP0247856A2

  公开（公告）日：1987-12-02

  Heterocyclic aromatic polymers are rapidly formed by contacting one or more appropriate multifunctional aromatic monomers, such as a diaminobenzenediol, a terephthaloyl halide and/or an aminohydroxybenzoic acid, with a sulfonic acid, as the solvent, and a dehydrating agent.

  将一种或多种适当的多功能芳香族单体（如二氨基苯二酚、对苯二甲酰卤和/或氨基羟基苯甲酸）与磺酸（作为溶剂）和脱水剂接触，可快速形成杂环芳香族聚合物。
• Chuiguk,V.A., Soviet progress in chemistry, 1973, vol. 39, # 4, p. 70 - 74
  作者：Chuiguk,V.A.

  DOI：——

  日期：——
• Synthesis and Evaluation of ¹⁸F-Labeled 2-Phenylbenzothiazoles as Positron Emission Tomography Imaging Agents for Amyloid Plaques in Alzheimer’s Disease
  作者：Kim Serdons、Christelle Terwinghe、Peter Vermaelen、Koen Van Laere、Hank Kung、Luc Mortelmans、Guy Bormans、Alfons Verbruggen

  DOI：10.1021/jm8013376

  日期：2009.3.12

  Imaging agents targeting amyloid beta(A beta) may be useful for early diagnosis and follow-up of treatment of patients with Alzheimer's disease (AD). Three of five tested 2-(4'-fluorophenyl)-1,3-benzothiazoles displayed high binding affinities for A beta plaques in AD human brain homogenates (K-i between 2.2 and 22.5 nM). They all contained the F-18-label directly attached to the aromatic ring and were synthesized starting from the nitro precursor. Determination of the partition coefficient, biodistribution studies in normal mice, and in vivo mu PET studies in normal rats showed that their initial brain uptake was high and brain washout was fast. The most promising compound [F-18]5, or 6- methyl-2-(4'-[F-18]fluorophenyl)-1,3-benzothiazole, seemed to be metabolically stable in the brain, and its plasma radiometabolites, which do not cross the blood-brain barrier, were determined. The preliminary results strongly suggest that this new fluorinated compound is a promising candidate as an A beta plaque imaging agent for the study of patients with AD.

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