4,5-dimethyl-o-phenylenediamine dihydrochloride

• 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: 4,5-dimethyl-o-phenylenediamine dihydrochloride
• 英文别名: 4,5-Dimethyl-o-phenylendiamin; Dihydrochlorid；(2-Amino-4,5-dimethylphenyl)azanium;chloride；(2-amino-4,5-dimethylphenyl)azanium;chloride
• 化学式: C₈H₁₂N₂*2ClH
• 分子量: 209.119
• InChiKey: MNFJOYIWZHDEKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.89
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  52
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,5-dimethyl-o-phenylenediamine dihydrochloride 在 sodium hydroxide 、 苄基三乙基氯化铵 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 2,3-Dimethyl-5,6,8,9-tetrahydro-7-thia-4b,10-diaza-benzo[a]azulene
  参考文献：
  名称：

  Synthesis and Structural Features of New Cyclofunctionalized Benzimidazoles

  摘要：

  The synthesis of new tricyclic derivatives having sulfur-containing six or seven-membered rings fused to the <> edge of benzimidazole system, is reported. The stereochemical characteristics of thiazino- and thiazepinobenzimidazoles (4-7) are described and comparative NMR data are discussed. The synthetic approach to new benzo- or pyridothiazinobenzimidazole tetracyclic systems (8) is also reported.

  DOI：

  10.3987/com-99-8784

文献信息

• Studies on saccharide benzimidazoles: 2-(β-D-gulofuranosyl)benzimidazole and 2-(β-D-glucofuranosyl)benzimidazole C-nucleoside analogs; synthesis, anomeric configuration and antifouling potency
  作者：Mohammed A.E. Sallam、Dalia M.S.A. Salem、Gorgina M.H. Labib、Trevena N.M.A. Youssef、Koichi Matsuo

  DOI：10.1016/j.carres.2020.108073

  日期：2020.10

  2-(D-gulo-) and 2-(D-gluco-)benzimidazole C-nucloside analogs have been prepared by condensation of o-phenylenediamine dihydrochloride derivatives with D-gulonic acid-γ-lactone and D-gluconic acid-γ-lactone, separately. Acid catalyzed dehydrative cyclization of the acyclic benzimidazole C-nucleoside afforded the corresponding 2-(β-D-gulo-) and 2-(β-D-gluco-)furanosyl benzimidazole C-nucleoside analogs. The

  通过邻苯二胺二盐酸盐衍生物与 D-古洛糖酸-γ-内酯和 D-葡萄糖酸缩合制备了一系列无环 2-(D-gulo-) 和 2-(D-gluco-) 苯并咪唑 C-核苷类似物酸-γ-内酯，分开。无环苯并咪唑C-核苷的酸催化脱水环化得到相应的2-(β-D-gulo-)和2-(β-D-葡糖-)呋喃糖基苯并咪唑C-核苷类似物。获得的C-核苷类似物的结构和异头构型通过高碘酸盐氧化、1H NMR、UV和圆二色性(CD)光谱确定。已使用抗菌生物膜试验研究了 C-核苷类似物的防污性能。2-(D-gulo-) 和 2-(D-gluco-) 苯并咪唑类似物可用于抑制海洋细菌的生长，并且不会对周围的海水造成任何不良影响。
• Discovery of novel benzimidazole acyclic <i>C</i>‐nucleoside DNA intercalators halting breast cancer growth
  作者：Mohamed N. Abd Al Moaty、Yeldez El Kilany、Laila Fathy Awad、Nihal Ahmed Ibrahim、Marwa M. Abu‐Serie、Amira El‐Yazbi、Mohamed Teleb

  DOI：10.1002/ardp.202300454

  日期：2024.1

  selective derivatives against MCF-7 (half-maximal inhibitory concentration [IC50] = 0.060 and 0.080 µM, selectivity index [SI] = 9.68 and 8.27, respectively) and MDA-MB-231 cells (IC50 = 0.299 and 0.166 µM, SI = 1.94 and 3.98, respectively). Thus, they were identified as the study hits for mechanistic studies. Both derivatives induced DNA damage at 0.24 and 0.29 μM, respectively. The DNA damage kinetics

  乳腺癌仍然是全世界最常见的癌症。在实践中，成功的临床结果是通过靶向 DNA 实现的。随着新型 DNA 靶向剂的引入取得进展，本文采用“糖方法”设计来开发带有与碳水化合物附属物相连的药效基序的新型嵌入剂。据此，合理设计、合成了新的苯并咪唑无环C核苷，并通过MTT（3-[4,5-二甲基噻唑-2-基]-2,5二苯基四唑溴化物）测定法评价其对MCF-7和MDA的细胞毒性。 -MB-231乳腺癌细胞与正常成纤维细胞（Wi-38）相比，与阿霉素相比。 ( 1S , 2R , 3S , 4R )-2-(1,2,3,4,5-五羟基)戊基-1H- 5,6-二氯苯并咪唑7和( 1S , 2R , 3S ,4 R )-2-(1,2,3,4,5-五羟基)戊基-1 H -萘噻咪唑13是针对 MCF-7 的最有效和选择性衍生物（半最大抑制浓度 [IC 50 ] = 0.060和 0.080 µM，选择性指数 [SI]
• Kaupp, Gerd; Pogodda, Uwe; Schmeyers, Jens, Chemische Berichte, 1994, vol. 127, # 11, p. 2249 - 2262
  作者：Kaupp, Gerd、Pogodda, Uwe、Schmeyers, Jens

  DOI：——

  日期：——
• MAOS of<scp>D</scp>‐Gluconic Acid,<scp>D</scp>‐Glucono‐1,4‐ and 1,5‐Lactones, Esters, Hydrazides, and Benzimidazoles Thereof
  作者：E. S. H. El Ashry、L. F. Awad、H. Abdel Hamid、A. I. Atta

  DOI：10.1080/07328300701540258

  日期：2007.9

  Microwave-assisted organic synthesis (MAOS) of D-gluconic acid can be efficiently done by oxidation of D- glucose with bromine water, upon irradiation with microwave ( MW). It was also used for the conversion of D-gluconic acid to ethyl D-gluconate, D-glucono-1,4- and 1,5-lactones, gluconyl hydrazide, and gluconyl phenylhydrazide in yields comparable to those obtained by conventional methods, but in much shorter times. A convenient microwave- mediated condensation of D- gluconic acid with o-phenylenediamines provided the respective acyclonucleoside benzimidazole in short time and good yield.[GRAPHICS]
• US7125883B1
  申请人：——

  公开号：US7125883B1

  公开（公告）日：2006-10-24