2-hydroxy-α,α-dichloroacetanilide | 14676-36-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-hydroxy-α,α-dichloroacetanilide
• 英文别名: 2,2-dichloro-N-(2-hydroxyphenyl)acetamide；N-dichloroacetyl-2-aminophenol；o-(dichloroacetamide)phenol；2-(2,2-dichloro-acetylamino)-phenol；2-(α,α-Dichloracetamido)-phenol；N-Dichloracetyl-o-aminophenol
• CAS: 14676-36-9
• 化学式: C₈H₇Cl₂NO₂
• mdl: MFCD15113367
• 分子量: 220.055
• InChiKey: ATATZRXAQVYVMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-hydroxy-α,α-dichloroacetanilide 反应 2.0h， 生成 2,4-二羟基-2H-1,4-苯并噁嗪-3(4h)-酮
  参考文献：
  名称：

  Matlin,S.A. et al., Journal of the Chemical Society. Perkin transactions I, 1979, p. 2481 - 2487

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基苯酚 以0%的产率得到
  参考文献：
  名称：

  Nagarajan K., Goud A. Nagana, Rao V. Ranga, Shah R. K., Shenoy S. J., Proc. Indian Acad. Sci. Chem. Sci., 104 (1992) N 5, S 549-568

  摘要：

  DOI：

文献信息

• Design, synthesis, molecular docking, biological evaluations and QSAR studies of novel dichloroacetate analogues as anticancer agent
  作者：Masood Fereidoonnezhad、S. Mohammad Hossein Tabaei、Amirhossein Sakhteman、Hassan Seradj、Zeinab Faghih、Zahra Faghih、Ayyub Mojaddami、Batool Sadeghian、Zahra Rezaei

  DOI：10.1016/j.molstruc.2020.128689

  日期：2020.12

  its proliferation. In this study, a series of novel N-aryl-2,2-dichloroacetamide and aryl-2,2-dichloroacetate derivatives were designed and synthesized. Their cytotoxic activities against various human cancer cell lines including A549, HCA-7, MCF-7, MDA-MB-231, KB and SKOV3 were evaluated. These compounds showed satisfactory potencies with much higher anticancer activity than the parent compound DCA

  摘要 二氯乙酸 (DCA) 作为线粒体靶向小分子，通过抑制丙酮酸脱氢酶激酶 (PDK1-4)，促进线粒体调节的细胞凋亡，从而抑制肿瘤生长并减少其增殖。在本研究中，设计并合成了一系列新型 N-芳基-2,2-二氯乙酰胺和芳基-2,2-二氯乙酸衍生物。评估了它们对各种人类癌细胞系（包括 A549、HCA-7、MCF-7、MDA-MB-231、KB 和 SKOV3）的细胞毒活性。与母体化合物 DCA 相比，这些化合物显示出令人满意的抗癌活性，对研究的癌细胞系具有更高的抗癌活性。还进行了分子对接研究以发现它们的结合位点以及它们与 PDK 同工酶的相互作用类型。在合成的化合物中，2,2-二氯-N-(9,10-dioxo-9, 10-dihydroanthracen-1-yl)acetamide (f1) 也可以诱导 A549 细胞凋亡。因此，化合物 f1 可能具有进一步研究药物开发的潜在价值。还使用一系列化学计量学方法探索了此类化合物的
• Yalcin, Ismail; Tekiner, Betul P.; Oren, Ilkay Yildiz, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 4, p. 905 - 909
  作者：Yalcin, Ismail、Tekiner, Betul P.、Oren, Ilkay Yildiz、Arpaci, Ozlem Temiz、Aki-Saner, Esin、Altanlar, Nurten

  DOI：——

  日期：——
• Gauss,W.; Heitzer,H., Justus Liebigs Annalen der Chemie, 1970, vol. 733, p. 59 - 69
  作者：Gauss,W.、Heitzer,H.

  DOI：——

  日期：——
• Chatterjee; Sharma; Banerji, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1990, vol. 29, # 2, p. 132 - 134
  作者：Chatterjee、Sharma、Banerji、Basa

  DOI：——

  日期：——
• Fate of Benzoxazinone Allelochemicals in Soil after Incorporation of Wheat and Rye Sprouts
  作者：Stine S. Krogh、Susanne J. M. Mensz、Susan T. Nielsen、Anne G. Mortensen、Carsten Christophersen、Inge S. Fomsgaard

  DOI：10.1021/jf051147i

  日期：2006.2.1

  Growing cereals (especially rye), which are incorporated into the soil to increase soil fertility or organic matter content, is a common practice in crop rotation. The additional sanitizing effect of this incorporation has often been appreciated and is said to be due to leaching of benzoxazinones and subsequent formation of benzoxazolinones. In this study wheat (Stakado) and rye (Hacada) sprouts were incorporated into soil in amounts that simulated agricultural practice. By extraction and subsequent LC-MS analysis the disappearance and appearance of benzoxazinones, benzoxazolinones, and phenoxazinones in soil were followed. In the wheat experiments 6-methoxybenzoxazolin-2-one (MBOA) was detected as the main compound. 2-Hydroxy-7-methoxy-1,4-benzoxazin-3-one (HMBOA) and 2-hydroxy-1,4-benzoxazin-3-one (HBOA) were detected as well. No phenoxazinones were detected. For the rye experiment the picture was more complex. In the first 2 days of incubation MBOA and 2,4-dihydroxy-1,4-benzoxazin-3-one (DIBOA) were detected as the main allelochemicals along with HBOA, HMBOA, and benzoxazolin-2-one (BOA), in decreasing order. Later in the incubation period some 2-amino-3H-phenoxazin-3-one (APO) was detected and the amount of HBOA increased considerably and decreased again. The profiling of the benzoxazinone metabolites and their derivates in soil was dynamic and time-dependent. The highest concentrations of most of the compounds were seen at day 1 after incorporation. A maximum concentration was reached at day 4 for a few of the compounds. This study is the first of its kind that shows the dynamic pattern of biologically active benzoxazinone derivates in soil after incorporation of wheat and rye sprouts. Methods for organic synthesis of HBOA and HMBOA were developed as part of the study.