2-氨基-7-甲基-4-苯并噻唑醇 | 7471-04-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 2-氨基-7-甲基-4-苯并噻唑醇
• 英文名称: 2-amino-7-methyl-1,3-benzothiazol-4-ol
• 英文别名: 2-Amino-4-hydroxy-7-methyl-benzthiazol；2-amino-7-methyl-benzothiazol-4-ol
• CAS: 7471-04-7
• 化学式: C₈H₈N₂OS
• 分子量: 180.23
• InChiKey: IOQRRTGEBXOWRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  87.4
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  依达拉奉 、 2-氨基-7-甲基-4-苯并噻唑醇 在 盐酸 、 sodium nitrite 作用下， 以 硫酸 、 溶剂黄146 为溶剂， 反应 4.0h， 生成 4-[(7-hydroxy-4-methyl-1,3-benzothiazol-2-yl)diazenyl]-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one
  参考文献：
  名称：

  Synthesis, characterization, and biological evaluation of 4-[(4-hydroxy-7-methyl-1,3-benzothiazol-2-yl) diazenyl]-5-methyl-2-phenyl-2,4-dihydro-3-pyrazol-3-one and its metal complexes

  摘要：

  New mononuclear Cu(II), Co(II) and Ni(II) complexes of novel azo-dye ligand 4-[(4-hydroxy-7-methyl-1,3-benzothiazol-2-yl)diazenyl]-5-methyl-2-phenyl-2,4-dihydro-3-pyrazol-3-one (L) with O,N-donor site were synthesized and are characterized by various spectroscopic techniques. The quantum chemical parameters were evaluated for all the compounds by ZINDO/1 semi-empirical method and are compared with the experimental data. Spectral investigations suggested the octahedral geometry for Co(II) and Ni(II) complexes and distorted tetrahedral geometry for Cu(II) complex. The antibacterial activity of the compounds was screened against different microbial strains and the results indicated that all the metal complexes exhibited higher activity than the free ligand. The interaction of pUC18 DNA with the synthesized compounds was explored by gel electrophoresis technique. All metal complexes exhibited significant cleavage activity against supercoiled pUC18 DNA. The anticancer activity of the compounds was studied against K562, A549, and MDA-MB-231 by MTT assay and all the metal chelates exhibited good anticancer properties.

  DOI：

  10.1080/00958972.2020.1787393
• 作为产物：
  描述：

  4-甲氧基-7-甲基苯并噻唑-2-胺 在 氢溴酸 作用下， 生成 2-氨基-7-甲基-4-苯并噻唑醇
  参考文献：
  名称：

  某些 Oxine 型化合物的螯合稳定性。二、4-羟基苯并噻唑1

  摘要：

  4-羟基苯并噻唑、2-氨基-4-羟基苯并噻唑、2-甲氨基-4-羟基苯并噻唑和 2-氨基-4-羟基-7-甲基苯并噻唑的酸解离常数在 50% v/v 对二恶烷中于 25 和通过 Calvin-Bjerrum 电位滴定技术获得配体与 Cu(II)、Pb(II)、Ni(H)、Co(II)、Zn(II) 和 Cd(II) 的螯合稳定性常数。将结果与先前报道的 8-羟基喹啉、4-羟基苯并咪唑和 4-羟基苯并恶唑的结果进行比较。4-羟基苯并噻唑螯合物的稳定性常数低于相应的8-羟基喹啉的稳定性常数。这是由较大的氮氧距离和供体氮原子上不利的电子取向来解释的。稳定性值高于 4-羟基苯并咪唑和 4-羟基苯并恶唑，这归因于 1-位较大硫原子的影响。（授权）

  DOI：

  10.1021/ja01471a002

文献信息

• NSD FAMILY INHIBITORS AND METHODS OF TREATMENT THEREWITH
  申请人：The Regents of the University of Michigan

  公开号：US20190183865A1

  公开（公告）日：2019-06-20

  Provided herein are small molecule inhibitors of NSD1, NSD2 and/or NSD3 activity, and methods of use thereof for the treatment of disease, including leukemia, breast cancer, osteosarcoma, lung and prostate cancers and other solid tumors as well as other diseases dependent on the activity of NSD1, NSD2 and/or NSD3.

  本文提供了NSD1、NSD2和/或NSD3活性的小分子抑制剂，以及利用这些抑制剂治疗疾病的方法，包括白血病、乳腺癌、骨肉瘤、肺癌、前列腺癌和其他实体肿瘤，以及其他依赖于NSD1、NSD2和/或NSD3活性的疾病。
• NSD family inhibitors and methods of treatment therewith
  申请人：The Regents of the University of Michigan

  公开号：US11324729B2

  公开（公告）日：2022-05-10

  Provided herein are small molecule inhibitors of NSD1, NSD2 and/or NSD3 activity, and methods of use thereof for the treatment of disease, including leukemia, breast cancer, osteosarcoma, lung and prostate cancers and other solid tumors as well as other diseases dependent on the activity of NSD1, NSD2 and/or NSD3.

  本文提供了NSD1、NSD2和/或NSD3活性的小分子抑制剂及其用于治疗疾病的方法，包括白血病、乳腺癌、骨肉瘤、肺癌和前列腺癌、其他实体瘤以及依赖于NSD1、NSD2和/或NSD3活性的其他疾病。
• Practical Synthesis of a Vanilloid Receptor-1 Antagonist
  作者：Oliver R. Thiel、Charles Bernard、Tony King、Mina Dilmeghani-Seran、Tracy Bostick、Robert D. Larsen、Margaret M. Faul

  DOI：10.1021/jo8002216

  日期：2008.5.1

  Small molecule TRPV1 antagonists have been a recent focus in the search for pain treatment agents. We herein describe a practical and scalable synthesis of AMG 628 (1), a bis-substituted pyrimidine derivative that was identified as a highly efficacious agent, suitable for clinical development. Highlights of our approach include a practical route to a substituted benzothiazole, a scalable synthesis of an enantiopure piperazine fragment, and identification of conditions for selective coupling reactions on 2,6-dichloropyrimidine, to access the active pharmaceutical ingredient in high purity and overall yield.
• Synthesis, characterization, and biological evaluation of 4-[(4-hydroxy-7-methyl-1,3-benzothiazol-2-yl) diazenyl]-5-methyl-2-phenyl-2,4-dihydro-3-pyrazol-3-one and its metal complexes
  作者：Mallikarjuna Niluvanji Matada、Keshavayya Jathi、Kiptoo Geoffry、Ravi Berenkere Nagarajappa、Harmesh Chander Tandon

  DOI：10.1080/00958972.2020.1787393

  日期：2020.5.18

  New mononuclear Cu(II), Co(II) and Ni(II) complexes of novel azo-dye ligand 4-[(4-hydroxy-7-methyl-1,3-benzothiazol-2-yl)diazenyl]-5-methyl-2-phenyl-2,4-dihydro-3-pyrazol-3-one (L) with O,N-donor site were synthesized and are characterized by various spectroscopic techniques. The quantum chemical parameters were evaluated for all the compounds by ZINDO/1 semi-empirical method and are compared with the experimental data. Spectral investigations suggested the octahedral geometry for Co(II) and Ni(II) complexes and distorted tetrahedral geometry for Cu(II) complex. The antibacterial activity of the compounds was screened against different microbial strains and the results indicated that all the metal complexes exhibited higher activity than the free ligand. The interaction of pUC18 DNA with the synthesized compounds was explored by gel electrophoresis technique. All metal complexes exhibited significant cleavage activity against supercoiled pUC18 DNA. The anticancer activity of the compounds was studied against K562, A549, and MDA-MB-231 by MTT assay and all the metal chelates exhibited good anticancer properties.
• Chelate Stabilities of Certain Oxine-type Compounds. II. 4-Hydroxybenzothiazoles¹
  作者：T. J. Lane、C. S. C. Lane、A. Sam

  DOI：10.1021/ja01471a002

  日期：1961.5

  The acid dissociation constants of 4-hydroxybenzothiazole, 2- amino-4- hydroxybenzothiazole, 2-methylamino-4hydroxybenzothiazole, and 2-amino-4-hydroxy- 7-methylbenzothiazole were determined in 50% v/v p-dioxane at 25 and the chelate stability constants of the ligands with Cu(II), Pb(II), Ni(H), Co(II), Zn(II), and Cd(II) were obtained by Calvin-Bjerrum potentiometric titration technique. The results

  4-羟基苯并噻唑、2-氨基-4-羟基苯并噻唑、2-甲氨基-4-羟基苯并噻唑和 2-氨基-4-羟基-7-甲基苯并噻唑的酸解离常数在 50% v/v 对二恶烷中于 25 和通过 Calvin-Bjerrum 电位滴定技术获得配体与 Cu(II)、Pb(II)、Ni(H)、Co(II)、Zn(II) 和 Cd(II) 的螯合稳定性常数。将结果与先前报道的 8-羟基喹啉、4-羟基苯并咪唑和 4-羟基苯并恶唑的结果进行比较。4-羟基苯并噻唑螯合物的稳定性常数低于相应的8-羟基喹啉的稳定性常数。这是由较大的氮氧距离和供体氮原子上不利的电子取向来解释的。稳定性值高于 4-羟基苯并咪唑和 4-羟基苯并恶唑，这归因于 1-位较大硫原子的影响。（授权）