3-Brom-4-methyl-thiophenol | 19075-64-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚类
• 英文名称: 3-Brom-4-methyl-thiophenol
• 英文别名: 3-Bromo-4-methyl-benzenethiol；3-bromo-4-methylbenzenethiol
• CAS: 19075-64-0
• 化学式: C₇H₇BrS
• 分子量: 203.103
• InChiKey: RGGIMPYCVUNPGX-UHFFFAOYSA-N

物化性质

• 沸点：
  125 °C(Press: 12 Torr)
• 密度：
  1.509±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-Brom-4-methyl-thiophenol 在 sodium periodate 、 sodium hydride 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.25h， 生成 2-溴-1-甲基-4-(丙基亚磺酰基)苯
  参考文献：
  名称：

  Discovery of Potent, Selective, and Orally Bioavailable Alkynylphenoxyacetic Acid CRTH2 (DP2) Receptor Antagonists for the Treatment of Allergic Inflammatory Diseases

  摘要：

  New phenoxyacetic acid antagonists of CRTH2 are described. Following the discovery of a hit compound by a focused screening, high protein binding was identified as its main weakness. Optimization aimed at reducing serum protein binding led to the identification of several compounds that showed not only excellent affinities for the receptor (41 compounds with K-i < 10 nM) but also excellent potencies in a human whole blood assay (IC50 < 100 nM; PGD2-induced eosinophil shape change). Additional optimization of the PK characteristics led to the identification of several compounds suitable for in vivo testing. Of these, 19k and 19s were tested in two different pharmacological models (acute FITC-mediated contact hypersensitivity and ovalbumin-induced eosinophilia models) and found to be active after oral dosing (10 and 30 mg/kg).

  DOI：

  10.1021/jm200866y
• 作为产物：
  描述：

  3-溴-4-甲基苯胺 在 盐酸 、 potassium hydroxide 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 10.75h， 生成 3-Brom-4-methyl-thiophenol
  参考文献：
  名称：

  Discovery of Potent, Selective, and Orally Bioavailable Alkynylphenoxyacetic Acid CRTH2 (DP2) Receptor Antagonists for the Treatment of Allergic Inflammatory Diseases

  摘要：

  New phenoxyacetic acid antagonists of CRTH2 are described. Following the discovery of a hit compound by a focused screening, high protein binding was identified as its main weakness. Optimization aimed at reducing serum protein binding led to the identification of several compounds that showed not only excellent affinities for the receptor (41 compounds with K-i < 10 nM) but also excellent potencies in a human whole blood assay (IC50 < 100 nM; PGD2-induced eosinophil shape change). Additional optimization of the PK characteristics led to the identification of several compounds suitable for in vivo testing. Of these, 19k and 19s were tested in two different pharmacological models (acute FITC-mediated contact hypersensitivity and ovalbumin-induced eosinophilia models) and found to be active after oral dosing (10 and 30 mg/kg).

  DOI：

  10.1021/jm200866y

文献信息

• Design, synthesis and anticancer activity of Michael-type thiol adducts of α-santonin analogue with exocyclic methylene
  作者：Jabeena Khazir、Darren L. Riley、Gousia Chashoo、Bilal Ahmad Mir、David Liles、Md. Ataul Islam、Shashank K. Singh、Ram A. Vishwakarma、Lynne A. Pilcher

  DOI：10.1016/j.ejmech.2015.07.022

  日期：2015.8

  Michael-type analogues were generated on the C-ring of α-santonin (α-methylene-γ-butyrolactone) upon reaction with various thiols. All the thiol adducts synthesized were evaluated for their anticancer activity against four human cancer cell lines (PC-3, HCT-15, A-549 and MCF-7). Bioassay results indicated that even though most of the synthesized compounds exhibited a good anticancer activity against various

  与各种硫醇反应后，在α-桑坦宁（α-亚甲基-γ-丁内酯）的C环上生成了一系列Michael型类似物。评估所有合成的硫醇加合物对四种人类癌细胞系（PC-3，HCT-15，A-549和MCF-7）的抗癌活性。生物测定结果表明，即使大多数合成的化合物在体外对各种癌细胞均表现出良好的抗癌活性，但仍发现某些化合物（如9e，9g和9q）是该系列中最有前途的类似物，其中化合物9e显示出IC 50分别在PC-3，MCF-7，A-549和HCT-116细胞系上的1.5μM，0.6μM，2.4μM和1.2μM值。此外，流式细胞术研究表明，用化合物9e，9g和9q处理的MCF-7细胞以浓度依赖的方式停滞在细胞周期的亚G1期。进一步研究了这些先导分子的NF-κB，p65转录因子抑制活性，证实了其对NF-κB，p65的浓度依赖性抑制作用，其中类似物9e在2μM时显示57％的抑制，9g在3μM时显示62％的抑制，而9q显示54
• [EN] PHENOXY ACETIC ACID DERIVATIVES<br/>[FR] DÉRIVÉS D'ACIDE PHÉNOXYACÉTIQUE
  申请人：MERCK SERONO SA

  公开号：WO2010092043A1

  公开（公告）日：2010-08-19

  The present invention provides phenoxyacetic acid derivatives of Formula (I) for the treatment of CRTH2 related disorders and disease selected from asthma, atopic dermatitis and inflammatory dermatoses.

  本发明提供了用于治疗与CRTH2相关的疾病和疾病（包括哮喘、特应性皮炎和炎症性皮肤病）的Formula（I）的苯氧乙酸衍生物。
• Process for preparing 6H-pyrido[1,2-c][1,3,5]benzothiadiazepines and
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US03946025A1

  公开（公告）日：1976-03-23

  Compounds of the formula ##SPC1## Exhibit central nervous system stimulating properties and act as muscle relaxants.

  化合物的分子式为##SPC1##，具有中枢神经系统刺激作用，并作为肌肉松弛剂。
• Pyridine containing compounds
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US03995042A1

  公开（公告）日：1976-11-30

  Compounds of the formula ##SPC1## And tautomers thereof, wherein R, R', R", Z, m and n are as defined hereinafter, exhibit central nervous system stimulating properties and act as muscle relaxants.

  公式##SPC1##及其互变异构体，其中R、R'、R"、Z、m和n的定义如下，表现出中枢神经系统刺激性质，并作为肌肉松弛剂。
• PHENOXY ACETIC ACID DERIVATIVES
  申请人：Crosignani Stefano

  公开号：US20110288066A1

  公开（公告）日：2011-11-24

  The present invention provides phenoxyacetic acid derivatives of Formula (I) for the treatment of CRTH2 related disorders and disease selected from asthma, atopic dermatitis and inflammatory dermatoses.

  本发明提供了公式(I)的苯氧乙酸衍生物，用于治疗与CRTH2相关的疾病和疾病，包括哮喘，特应性皮炎和炎症性皮肤病。