3,4-dichloroaniline hydrochloride | 33240-95-8

• 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: 3,4-dichloroaniline hydrochloride
• 英文别名: 3,4-Dichlor-anilin-hydrochlorid；(3,4-Dichlorophenyl)azanium;chloride；(3,4-dichlorophenyl)azanium;chloride
• CAS: 33240-95-8
• 化学式: C₆H₅Cl₂N*ClH
• 分子量: 198.479
• InChiKey: XANZVOMCLKMKMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26
• 氢给体数：
  2
• 氢受体数：
  1

安全信息

• 海关编码：
  2921420090

反应信息

• 作为反应物：
  描述：

  3,4-dichloroaniline hydrochloride 在 氨 、 溴 、 potassium carbonate 作用下， 以 乙醇 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.25h， 生成 (2-bromoethyl)-(5,6-dichlorobenzothiazol-2-yl)amine
  参考文献：
  名称：

  Synthesis, cytotoxic evaluation, and in silico studies of substituted N-alkylbromo-benzothiazoles

  摘要：

  In efforts to develop a new class of anticancer agents with improved efficacy and selective action, a series of N-alkylbromo-benzothiazoles were synthesized and evaluated for in vitro cytotoxic activity against various human cancer cell lines such as lung (A-549), prostate (PC-3), leukemia (THP-1), and colon (Caco-2). They were found to be highly active against prostate (PC-3) and leukemia (THP-1) cancer cells, moderately active against colon (Caco-2) cancer cells and less active against lung (A-549) cancer cells. Of the 12 compounds, two (11d, 11j) exhibit IC50 values of a parts per thousand currency sign 1 mu M against leukemia (THP-1) cancer cell lines. Compound 11l showed significant cytotoxic activity against the PC-3 (IC50 = 0.6 mu M), THP-1 (IC50 = 3 mu M) and Caco-2 cell lines (IC50 = 9.9 mu M), respectively. Docking study of the synthesized ligand was done on epidermal growth factor receptor using ArgusLab flexible docking, to determine their observed activity. Further QSAR investigations with stepwise multiple linear regression analysis were applied to find correlation between various physicochemical parameters and anticancer activity. The QSAR results showed that anticancer activity could be modeled with descriptors. The predictive ability of models was cross-validated by observation of the low residual activity values and adjusted coefficient of variation () obtained by leave-one-out technique.

  DOI：

  10.1007/s00044-012-0424-0
• 作为产物：
  描述：

  3,4-二氯苯胺 在 氯化亚砜 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 13.5h， 生成 3,4-dichloroaniline hydrochloride
  参考文献：
  名称：

  A facile and efficient method for the selective deacylation of N-arylacetamides and 2-chloro-N-arylacetamides catalyzed by SOCl2

  摘要：

  亚硫酰氯在无水条件下高效且选择性地促进了N-芳基乙酰胺和2-氯-N-芳基乙酰胺的去酰化反应，且不影响酯基、氨基磺酰基或苄氧酰胺基。这种方法已成功应用于多种底物，包括不同的N-芳基乙酰胺和2-氯-N-芳基乙酰胺，具有试剂成本低、选择性好、产率高、反应时间短和操作简便等吸引人的优点。这种新方法可能被用于选择性地在芳香族酰胺和烷基酰胺之间进行去酰化反应。

  DOI：

  10.1007/s11164-011-0327-6
• 作为试剂：
  描述：

  3,4-二氯苯胺 、 (E)-methyl 2-cyano-3-(furan-2-yl)acrylate 在 乙醇 、 3,4-dichloroaniline hydrochloride 作用下， 生成 2-cyano-3-[1-(3,4-dichloro-phenyl)-pyrrol-2-yl]-acrylic acid methyl ester
  参考文献：
  名称：

  Leditschke, Chemische Berichte, 1952, vol. 85, p. 483,486

  摘要：

  DOI：

文献信息

• Synthesis and evaluation of N-substituted cis-N-methyl-2-(1-pyrrolidinyl)cyclohexylamines as high affinity .sigma. receptor ligands. Identification of a new class of highly potent and selective .sigma. receptor probes
  作者：Brian R. De Costa、Wayne D. Bowen、Andrew Thurkauf、Daniel T. Finn、Sondra Vazirani、Richard B. Rothman、Linda Band、Patricia C. Contreras、Nancy M. Gray

  DOI：10.1021/jm00173a030

  日期：1990.11

  2R-(+)-, and 1R,2S-(-)-cis-2-(1-pyrrolidinyl)-N-methylcyclohexylamines. Analysis of sigma ([3H](+)-3-PPP), kappa ([3H]bremazocine and [3H]U69,593), dopamine-d2 ([3H](-)-sulpiride), and phencyclidine (PCP) ([3H]TCP) receptor binding in guinea pig brain revealed a number of highly potent and selective sigma receptor ligands. Notably, 1S,2R-cis-(-)-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]-(2-naphthyl) acetamide

  最近报道某些苯乙酰胺[（-）-和（+）-顺-3,4-二氯-N-甲基-N- [2-（1-吡咯烷基）环己基]苯乙酰胺]是有效的σ受体配体。为了确定是否可以提高对sigma受体的功效，合成了一系列与苯乙酰胺有关的化合物N-取代的顺式-2-（1-吡咯烷基）-N-甲基环己胺，并确定了其结构活性的要求。通过从先前报道的（+/-）-，1S，2R-（+）-和1R，2S-（-）-顺-2-（1-吡咯烷基）-N-甲基环己胺开始合成化合物。σ（[3H]（+）-3-PPP），kappa（[3H] bremazocine和[3H] U69,593），多巴胺-d2（[3H]（-）-舒必利）和苯环利定（PCP）的分析（[3H] TCP）受体在豚鼠脑中的结合揭示了许多高效和选择性的sigma受体配体。值得注意的是，1S，2R-顺-（-）-N-甲基-N- [2-（1-吡咯烷基）环己基]-（2-萘基）乙酰胺[（-）-29]（Ki
• INHIBITION OF OLIG2 ACTIVITY
  申请人：Curtana Pharmaceuticals, Inc.

  公开号：US20160237069A1

  公开（公告）日：2016-08-18

  Described herein are compounds and pharmaceutical compositions containing such compounds, which inhibit the activity of Olig2. Also described herein are methods of using such Olig2 inhibitors, alone and in combination with other compounds, for treating cancer and other diseases. In particular the Olig2 inhibitors may be used to treat glioblastoma.

  本文描述了含有这些化合物的化合物和药物组合物，这些化合物抑制Olig2的活性。本文还描述了使用这种Olig2抑制剂的方法，单独或与其他化合物结合，用于治疗癌症和其他疾病。特别是Olig2抑制剂可以用于治疗胶质母细胞瘤。
• BACTERIOSTATS: V. THE PREPARATION AND BACTERIOSTATIC PROPERTIES OF AMIDINE DERIVATIVES
  作者：D. L. Garmaise、R. W. Kay、R. Gaudry、H. A. Baker、A. F. McKay

  DOI：10.1139/v61-189

  日期：1961.7.1

  A number of polyamidines, N-substituted amidines, and diamidines were prepared for evaluation as bacteriostats. N,N′-Bis-(3,4-dichlorobenzyl)-sebacamidine dihydrochloride was the most active compou...

  制备了许多聚脒、N-取代脒和二脒，用于评价作为抑菌剂。N,N'-双-(3,4-二氯苄基)-癸二脒二盐酸盐是活性最强的化合物...
• Haloanilino Derivatives of Pyrimidines, Purines, and Purine Nucleoside Analogs: Synthesis and Activity against Human Cytomegalovirus
  作者：Maria Medveczky、Te-Fang Yang、Joseph Gambino、Peter Medveczky、George E. Wright

  DOI：10.1021/jm00010a026

  日期：1995.5

  DNA synthesis by human cytomegalovirus (HCMV)-infected human embryonic lung (HEL) cells in culture. In general, active compounds had moderate to low selectivity for viral vs host cell DNA synthesis. Nucleoside and acyclonucleoside analogs of 2-(3,5-dichloroanilino)purines inhibited both HCMV and cellular DNA synthesis at similar concentrations. 2-Amino-4-chloro-6-(3,5-dichloroanilino)pyrimidine and

  在苯胺环上带有3,4-或3,5-二氯取代基的2-苯胺嘌呤和6-苯胺基嘧啶可抑制人巨细胞病毒（HCMV）感染的人胚肺（HEL）细胞培养的病毒特异性DNA合成。通常，活性化合物对病毒与宿主细胞DNA的合成具有中等至低的选择性。2-（3,5-二氯苯胺基）嘌呤的核苷和无环核苷类似物以相似的浓度抑制HCMV和细胞DNA的合成。2-Amino-4-chloro-6-（3,5-dichloroanilino）pyrimidine和几种相关化合物在产量降低试验中以对HEL细胞无毒的浓度抑制了HCMV生长。
• Phosphorus pentoxide in organic synthesis. XX. Synthesis of<i>N</i>-aryl-7<i>H</i>-pyrrolo[2,3-d]pyrimidin-4-amines
  作者：Anker Jørgensen、Khairy A. M. El-Bayouki、Erik B. Pedersen

  DOI：10.1002/jhet.5570220351

  日期：1985.5

  N-Aryl-7H-pyrrolo[2,3-d]pyrimidine-4-amines 7 were prepared in 30-67% yields by treating N7-(1-phenyl-ethyl)pyrrolo[2,3-d]pyrimidin-4(3H)-ones 2 with a mixture of phosphorus pentoxide, triethylamine hydrochloride, and an appropriate arylamine hydrochloride at 240° for 3-7 hours.

  ñ -芳基- 7 ħ吡咯并[2,3- d ]嘧啶-4-胺7在30-67％的收率通过处理N7-（1-苯基-乙基）吡咯并[2,3制备d ]嘧啶4（3 H）-ones 2与五氧化二磷，三乙胺盐酸盐和适当的芳基胺盐酸盐的混合物在240°C搅拌3-7小时。