Phenol, 4-[(2-benzothiazolylimino)methyl]-2-methoxy- | 114260-39-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: Phenol, 4-[(2-benzothiazolylimino)methyl]-2-methoxy-
• 英文别名: (3-methoxy-4-hydroxy-1-benzaldehydo)-2-aminobenzothiazole
• CAS: 114260-39-8
• 化学式: C₁₅H₁₂N₂O₂S
• 分子量: 284.338
• InChiKey: DBOYNVRNDKFRSU-UHFFFAOYSA-N

物化性质

• 熔点：
  166-168 °C
• 沸点：
  484.3±55.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  54.71
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  巯基乙酸 、 Phenol, 4-[(2-benzothiazolylimino)methyl]-2-methoxy- 反应 0.08h， 生成 3-(benzo[d]thiazol-2-yl)-2-(4-hydroxy-3-methoxyphenyl)thiazolidin-4-one
  参考文献：
  名称：

  Green synthesis of thiazol-2-ylthiazolidin-4-ones as potential antifungals

  摘要：

  MORE (Microwave oriented reaction enhancement) green methodology was utilized to synthesize benzothiazol/thiazol-2-ylthiazolidin-4-ones and relatively assayed for their antifungal activity w.r.t precursors against three agriculturally important phytopathogenic fungi viz. Colletotrichum falcatum, Pyricularia grisea and Ustilago hordei. Thiazol-2-ylthiazolidin-4-ones displayed better inhibition of growth of fungi than their precursor's thiazol-2-amines, with some compounds showing results comparable to their standard fungicides endorsing the effectiveness of chemical hybridization of thiazoles/benzothiazoles with thiazolidin-4-ones in a single molecule. In silico toxicity of all the compounds was found to be equivalent to the standard fungicides. Lipinski parameters were used to rationalize structure activity relation using statistical analysis software.

  DOI：

  10.1134/s10704272150120253
• 作为产物：
  描述：

  苯胺 在 溴 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.08h， 生成 Phenol, 4-[(2-benzothiazolylimino)methyl]-2-methoxy-
  参考文献：
  名称：

  Green synthesis of thiazol-2-ylthiazolidin-4-ones as potential antifungals

  摘要：

  MORE (Microwave oriented reaction enhancement) green methodology was utilized to synthesize benzothiazol/thiazol-2-ylthiazolidin-4-ones and relatively assayed for their antifungal activity w.r.t precursors against three agriculturally important phytopathogenic fungi viz. Colletotrichum falcatum, Pyricularia grisea and Ustilago hordei. Thiazol-2-ylthiazolidin-4-ones displayed better inhibition of growth of fungi than their precursor's thiazol-2-amines, with some compounds showing results comparable to their standard fungicides endorsing the effectiveness of chemical hybridization of thiazoles/benzothiazoles with thiazolidin-4-ones in a single molecule. In silico toxicity of all the compounds was found to be equivalent to the standard fungicides. Lipinski parameters were used to rationalize structure activity relation using statistical analysis software.

  DOI：

  10.1134/s10704272150120253

文献信息

• Khosa, Muhammad Kaleem; Chatha, Shahzad Ali Shahid; Nisar, Madhia, Journal of the Chemical Society of Pakistan, 2011, vol. 33, # 3, p. 421 - 425
  作者：Khosa, Muhammad Kaleem、Chatha, Shahzad Ali Shahid、Nisar, Madhia、Zia, Khalid Mahmood、Khalil-Ur-Rehman、Jamal, Muhammad Asghar、Yousaf, Muhammad

  DOI：——

  日期：——
• Ashraf, Muhammad Aqeel; Wajid, Abdul; Mahmood, Karamat, Oriental Journal of Chemistry, 2011, vol. 27, # 2, p. 363 - 372
  作者：Ashraf, Muhammad Aqeel、Wajid, Abdul、Mahmood, Karamat、Maah, Mohd. Jamil、Yusoff, Ismail

  DOI：——

  日期：——
• Novel thiazolyl, thiazolinyl and benzothiazolyl Schiff bases as possible lipoxygenase's inhibitors and anti-inflammatory agents
  作者：Athina Geronikaki、Dimitra Hadjipavlou-Litina、Maria Amourgianou

  DOI：10.1016/s0014-827x(03)00065-x

  日期：2003.7

  In continuation of our previous research, several new thiazolyl/thiazolinyl/benzothiazolyl Schiff bases have been designed, synthesized and identified. The referred compounds are reported to act as lipoxygenase inhibitors affecting inflammation and/or psoriasis. The compounds were screened for their reducing activity (with the stable free radical 1,1-diphenyl-2-picryl-hydrazyl, DPPH) and for inhibition of soybean lipoxygenase (LOX). Anti-inflammatory activity was examined in vivo using the carrageenin induced mice paw edema (32.6-75%). The results are discussed in terms of structural and physicochemical characteristics of the compounds. Compound 2d possessed the highest inhibition 75%.
• Mishra, V.; Saksena, D. K.; Jain, M. C., Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 1987, vol. 17, p. 987 - 1002
  作者：Mishra, V.、Saksena, D. K.、Jain, M. C.

  DOI：——

  日期：——