2-(4-chlorophenyl)-6-methoxybenzo[d]thiazole | 92161-47-2

• 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-(4-chlorophenyl)-6-methoxybenzo[d]thiazole
• 英文别名: 2-(4-chlorophenyl)-6-methoxy-1,3-benzothiazole
• CAS: 92161-47-2
• 化学式: C₁₄H₁₀ClNOS
• 分子量: 275.759
• InChiKey: IAOQAZIOISGMFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  50.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  8-Chloro-4-methoxy-7,8lambda4-dithia-9-azabicyclo[4.3.0]nona-1(6),2,4,8-tetraene 在 水 、 sodium acetate 、 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 反应 0.83h， 生成 2-(4-chlorophenyl)-6-methoxybenzo[d]thiazole
  参考文献：
  名称：

  Sawhney, S N; Sharma, P. K.; Bajaj, K, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1994, vol. 33, p. 280 - 284

  摘要：

  DOI：

文献信息

• Efficient 2-Aryl Benzothiazole Formation from Aryl Ketones and 2-Aminobenzenethiols under Metal-Free Conditions
  作者：Yunfeng Liao、Hongrui Qi、Shanping Chen、Pengcheng Jiang、Wang Zhou、Guo-Jun Deng

  DOI：10.1021/ol302902e

  日期：2012.12.7

  2-Aryl benzothiazole formation from aryl ketones and 2-aminobenzenethiols under metal- and I2-free conditions was described. Various 2-aryl benzothiazoles were selectively obtained in good yields using molecular oxygen as oxidant. DMSO played an important role in this transformation. Functional groups such as methyl, methoxy, fluoro, chloro, bromo and nitro groups were tolerated under the optimized reaction

  描述了在无金属和无I 2的条件下由芳基酮和2-氨基苯硫醇形成的2-芳基苯并噻唑。使用分子氧作为氧化剂，可以高收率选择性地获得各种2-芳基苯并噻唑。DMSO在此转型中发挥了重要作用。在优化的反应条件下，可以容忍甲基，甲氧基，氟，氯，溴和硝基等官能团。
• An efficient desulfitative C–C cross coupling of fused thiazolidine-2-thione with boronic acids and boronic acid pinacol esters: formation of fused thiazoles
  作者：Kandasamy Rajaguru、Arumugam Mariappan、Ramachandran Manjusri、Shanmugam Muthusubramanian、Nattamai Bhuvanesh

  DOI：10.1039/c5ra17827d

  日期：——

  An efficient Pd(0)-catalyzed Cu(I)-mediated desulfitative C–C cross-coupling of benzo-fused thiazolidine-2-thione with boronic acids under neutral Liebeskind–Srogl conditions is described. The desulfitative cross coupling of boronic acid pinacol esters has also been demonstrated with fused thiazolidine-2-thione under basic conditions to afford fused thiazoles with good to excellent yields.

  描述了在中性Liebeskind-Srogl条件下有效的Pd（0）催化的Cu（I）介导的苯并稠合的噻唑烷-2-硫酮与硼酸的铜（I）介导的脱硫C-C交叉偶联。还已经证明在碱性条件下用稠合的噻唑烷-2-硫酮与硼酸频哪醇酯进行脱硫交叉偶联，从而以良好或极好的收率得到稠合的噻唑。
• Synthesis of 2-Aryl Benzothiazoles via K2S2O8-Mediated Oxidative Condensation of Benzothiazoles with Benzylamines
  作者：Ze Tan、Ji-Cheng Shi、Zhiyong Yang、Anwei Wang、Xiang Chen、Qingwen Gui、Jidan Liu、Hua Wang

  DOI：10.1055/s-0033-1339193

  日期：——

  A novel way to synthesize 2-arylbenzothiazoles is described. Reactions of benzothiazoles with diverse benzylamines in the presence of K2S2O8 and KOt-Bu in DMSO-H2O afforded the desired 2-arylbenzothiazoles in good yields. It is notable that no transition-metal catalyst is needed in this reaction. Compared with other known methods, this method of synthesizing 2-arylbenzothiazoles can be advantageous in cases where substituted benzothiazoles and benzylamines are readily available.
• 827. Some anti-microbial compounds in the heterocyclic series. Part III. Basic ethers of the benzothiazole and benzoxazole series
  作者：H. D. Cossey、C. J. Sharpe、F. F. Stephens

  DOI：10.1039/jr9630004322

  日期：——
• A Basis for Reduced Chemical Library Inhibition of Firefly Luciferase Obtained from Directed Evolution
  作者：Douglas S. Auld、Ya-Qin Zhang、Noel T. Southall、Ganesha Rai、Marc Landsman、Jennifer MacLure、Daniel Langevin、Craig J. Thomas、Christopher P. Austin、James Inglese

  DOI：10.1021/jm8014525

  日期：2009.3.12

  We measured the "druggability" of the ATP-dependent luciferase derived from the firefly Photuris pennsylvanica that was optimized using directed evolution (Ultra-Glo, Promega). Quantitative high-throughput screening (qHTS) was used to determine IC(50)S of 198899 samples against a formulation of Ultra-Glo luciferase (Kinase-Glo). We found that only 0.1 % of the Kinase-Glo inhibitors showed an IC(50) < 10 mu M compared to 0.9% found from a previous qHTS against the firefly luciferase from Photinus pyralis (lucPpy). Further, the maximum affinity identified in the lucPpy qHTS was 50 nM, while for Kinase-Glo this value increased to 600 nM. Compounds with interactions stretching outside the luciferin binding pocket were largely lost with Ultra-Glo luciferase. Therefore, Ultra-Glo luciferase will show less compound interference when used as an ATP sensor compared to lucPpy. This study demonstrates the power of large-scale quantitative analysis of structure-activity relationships (> 100K compounds) in addressing important questions such as a target's druggability.