2-aminobenzothiazole-6-carboxylic acid hydrochloride

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-aminobenzothiazole-6-carboxylic acid hydrochloride
• 英文别名: 6-Carboxy-1,3-benzothiazol-2-aminium chloride；2-amino-1,3-benzothiazol-3-ium-6-carboxylic acid;chloride
• 化学式: C₈H₆N₂O₂S*ClH
• mdl: MFCD01333078
• 分子量: 230.675
• InChiKey: UTKWPETXSJOITB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.83
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-aminobenzothiazole-6-carboxylic acid hydrochloride 在 sodium dithionite 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 36.0h， 生成 2-(2-hydroxyphenyl)benzo[d]thiazole-6-carboxylic acid
  参考文献：
  名称：

  设计，合成和评估作为多功能试剂的苯并噻唑衍生物。

  摘要：

  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。

  DOI：

  10.1016/j.bioorg.2020.103960
• 作为产物：
  描述：

  2-氨基苯并噻唑-6-羧酸乙酯 在 盐酸 作用下， 反应 5.0h， 以545 mg的产率得到2-aminobenzothiazole-6-carboxylic acid hydrochloride
  参考文献：
  名称：

  Optimization of a coagulation factor VIIa inhibitor found in factor Xa inhibitor library☆

  摘要：

  An inhibitor of the complex of factor Vila and tissue factor (fVIIa/TF), 2-substituted-4-amidinophenylpyruvic acid la, was structurally modified with the aim of increasing its potency and selectivity. The lead compound la was originally found in our factor Xa (fXa) inhibitor library on the basis of structural similarity of the primary binding sites of tVIIa and fXa. The design was based on computational docking studies using the extracted active site of tVIIa. Compound 1j was found to inhibit factor VIIa/TF at nanomolar concentration with improved selectivity versus fXa and thrombin and it preferentially prolonged the clotting time in the TF-dependent extrinsic pathway. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.12.033

文献信息

• WATER-SOLUBLE POLYMER-BASED CANTHARIMIDES AS POTENTIALLY SELECTIVE ANTI-TUMOR AGENTS
  申请人：Tang Johnny Cheuk-on

  公开号：US20100273840A1

  公开（公告）日：2010-10-28

  A cantharimide compound may include the backbone of formula (1). R 1 , R 2 , R 3 , and R 4 may be independently selected from the group consisting of H, C(O)OR 5 , C(O)R 6 , C(O)NR 7 R 8 , NR 9 C(O)R 10 , N—R 11 R 12 , O—R 13 , S—R 14 , P(O)(OR 15 )(OR 16 ), As(O)(OR 17 )(OR 18 ), SO 2 R 19 , SO 3 R 20 , and B(OR 21 ). X 1 to X 4 may be independently selected from the group consisting of nitrogen and carbon, such that X 1 to X 4 are not all hydrogen. Y 1 , Y 2 and R 5 to R 21 may be independently selected from the group consisting of hydrogen, C 1-12 -alkyl, -aryl, heteroaryl, and a bioactive polymer.

  一种鞣酰亚胺化合物可能包括式（1）的骨架。R1、R2、R3和R4可以独立地从H、C（O）OR5、C（O）R6、C（O）NR7R8、NR9C（O）R10、N—R11R12、O—R13、S—R14、P（O）（OR15）（OR16）、As（O）（OR17）（OR18）、SO2R19、SO3R20和B（OR21）的组中选择。X1到X4可以独立地从氮和碳的组中选择，使得X1到X4不全为氢。Y1、Y2和R5到R21可以独立地从氢、C1-12-烷基、芳基、杂芳基和生物活性聚合物的组中选择。
• Amidinophenylpyruvic acid derivatives
  申请人：AJINOMOTO CO. INC

  公开号：US20030109547A1

  公开（公告）日：2003-06-12

  An amidinophenylpyruvic acid derivative of the following formula, analogs thereof and pharmaceutically acceptable salts thereof have an excellent antagonistic effect against activated blood coagulation factor VII. 1

  以下是该公式的一种氨基苯丙酸衍生物，其类似物和药学上可接受的盐具有出色的对激活的凝血因子VII的拮抗作用。
• 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
• AMIDINOPHENYLPYRUVIC ACID DERIVATIVE
  申请人：Ajinomoto Co., Inc.

  公开号：EP1236712A1

  公开（公告）日：2002-09-04

  An amidinophenylpyruvic acid derivative of the following formula, analogs thereof and pharmaceutically acceptable salts thereof have an excellent antagonistic effect against activated blood coagulation factor VII.

  下式中的脒苯基丙酮酸衍生物、其类似物和药学上可接受的盐类对活化的凝血因子 VII 有极好的拮抗作用。
• Antirheumatic Agents:  Novel Methotrexate Derivatives Bearing a Benzoxazine or Benzothiazine Moiety
  作者：Hiroharu Matsuoka、Nobuhiro Ohi、Masahiko Mihara、Hiroshi Suzuki、Katsuhito Miyamoto、Noriaki Maruyama、Keiichiro Tsuji、Nobuaki Kato、Toshio Akimoto、Yasuhisa Takeda、Keiichi Yano、Toshio Kuroki

  DOI：10.1021/jm9605288

  日期：1997.1.1

  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.