ethyl 4-amino-3-nitrobenzenecarboximidate hydrochloride | 54998-39-9

• 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: ethyl 4-amino-3-nitrobenzenecarboximidate hydrochloride
• 英文别名: 4-amino-3-nitrophenylimidic acid ethyl ester hydrochloride；4-amino-3-nitrobenzimidic acid ethyl ester hydrochloride；ethyl 4-amino-3-nitrobenzene-1-carboximidate hydrochloride；ethyl 3-nitro-4-benzenamineimidate hydrochloride；ethyl-4-amino-3-nitrobenzenecarboxamidate hydrochloride；Ethyl 4-amino-3-nitrobenzimidate hydrochloride；ethyl 4-amino-3-nitrobenzenecarboximidate;hydrochloride
• CAS: 54998-39-9
• 化学式: C₉H₁₁N₃O₃*ClH
• 分子量: 245.666
• InChiKey: BCTMWQJDHMKVQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.96
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 4-amino-3-nitrobenzenecarboximidate hydrochloride 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 72.0h， 生成 4-[N-(N-morpholinyl)]amidino-1,2-phenylenediamine
  参考文献：
  名称：

  New Amidino-benzimidazolyl Derivatives of Tylosin and Desmycosin.

  摘要：

  新型胍基苯并咪唑衍生物的抗生素酮霉素和去甲霉素是通过相应的胍基取代的邻苯二胺与酮霉素或去甲霉素在20-C醛基的反应制备的。该反应在无水乙醇中，在对苯醌的存在下进行。通过这种方法制备了：20-[5-(N-异丙胍基)-2-苯并咪唑基]酮霉素盐酸盐 9，20-[5-(2-咪唑啉基)-2-苯并咪唑基]酮霉素盐酸盐 10，20-[5-(N-吗啉基胍基)-2-苯并咪唑基]酮霉素盐酸盐 11，20-[5-(N-异丙胍基)-2-苯并咪唑基]去甲霉素盐酸盐 12，20-[5-(2-咪唑啉基)-2-苯并咪唑基]去甲霉素盐酸盐 13，20-[5-(N-吗啉基胍基)-2-苯并咪唑基]去甲霉素盐酸盐 14。对其抗微生物活性进行了测试，测试了一系列微生物。

  DOI：

  10.7164/antibiotics.55.308
• 作为产物：
  描述：

  4-乙酰氨苯甲腈 在 盐酸 、 硫酸 、 potassium nitrate 作用下， 反应 2.75h， 生成 ethyl 4-amino-3-nitrobenzenecarboximidate hydrochloride
  参考文献：
  名称：

  Kelly, David P.; Bateman, Stuart A.; Martin, Roger F., Australian Journal of Chemistry, 1994, vol. 47, # 2, p. 247 - 262

  摘要：

  DOI：

文献信息

• [EN] RADIOPROTECTOR COMPOUNDS AND METHODS<br/>[FR] COMPOSÉS RADIOPROTECTEURS ET PROCÉDÉS CORRESPONDANTS
  申请人：PETER MACCALLUM CANCER INST

  公开号：WO2011123890A1

  公开（公告）日：2011-10-13

  The invention relates to novel compounds, processes for their preparation and their use in protecting biological materials from radiation damage (radioprotection). Preferred compounds of the invention are those of Formula (II), as follows: wherein W represents -N(R1R2) where R1 and R2 are not both hydrogen and where they may together form a 5, 6 or 7 membered ring structure, -NHN(R1R2), NHR3N(R1R2), -NHR3OR2, -N(R3)R3OR2, -N(R1)R3OR3OR3, OR3NR1R2, -OR3 or W represents piperidyl, piperazinyl, morpholinyl, thiomorpholinyl or diazepanyl each of which may be optionally substituted by C1 to C4 alkyl, C2 to C4 alkenyl, -N(CO)N(R1R2), -N(CO)OR1, -N(CO)OR3OH, -(CO)NR1R2, -R3(CO)NR1R2, -R3OR1, -OR1, -N(R1R2) OR -NH-; R1 and R2 are the or different and are selected from hydrogen, C1 to C4 alkyl or C2 to C4 alkenyl; group or chain; Z is the same or different and represents N or CH; Z' is the same or different and represents N or C; X represents CH, N or NH, where ⃜⃜ is a double bond when X is CH or N and a single bond when X is NH; X' represents N or NH, wherein when X is CH or N X' is NH and wherein X and X' are different and further where ≃≃≃is a double bond when X' is N and a single bond when X' is NH; Q represents H, alkoxyl, -NR1R2, F or Cl; Q1 is absent when Z' is N and when Z' is C it represents H, alkoxyl, -NR1R2, F or Cl; A represents a five to ten membered single or multiple ring structure with heterocyclic N or O located at the ortho position, said ring including optional double bonds, substitutions and/or other heteroatoms and pharmaceutically acceptable derivatives thereof.

  该发明涉及新化合物、其制备方法以及它们在保护生物材料免受辐射损伤（辐射防护）方面的用途。该发明的优选化合物为以下式（II）的化合物：其中W代表-N（R1R2），其中R1和R2不同时为氢，它们可以共同形成一个5、6或7元环结构，-NHN（R1R2）、NHR3N（R1R2）、-NHR3OR2、-N（R3）R3OR2、-N（R1）R3OR3OR3、OR3NR1R2、-OR3或W代表哌啶基、哌嗪基、吗啉基、硫代吗啉基或二氮杂环庚烷基，每种基可能被C1至C4烷基、C2至C4烯基、-N（CO）N（R1R2）、-N（CO）OR1、-N（CO）OR3OH、-（CO）NR1R2、-R3（CO）NR1R2、-R3OR1、-OR1、-N（R1R2）或-NH-取代；R1和R2相同或不同，选自氢、C1至C4烷基或C2至C4烯基；Z相同或不同，代表N或CH；Z'相同或不同，代表N或C；X代表CH、N或NH，其中当X为CH或N时为双键，当X为NH时为单键；X'代表N或NH，其中当X为CH或N时X'为NH，且X和X'不同，进一步当X'为N时为双键，当X'为NH时为单键；Q代表H、烷氧基、-NR1R2、F或Cl；当Z'为N时Q1不存在，当Z'为C时，Q1代表H、烷氧基、-NR1R2、F或Cl；A代表一个含有杂环N或O的五至十元单环或多环结构，位于邻位，该环包括可选的双键、取代基和/或其他杂原子及其药用可接受的衍生物。
• [EN] INHIBITORS OF HISTONE DEACETYLASE<br/>[FR] INHIBITEURS D'HISTONE DEACETYLASE
  申请人：METHYLGENE INC

  公开号：WO2005030704A1

  公开（公告）日：2005-04-07

  The invention relates to the inhibition of histone deacetylase. The invention provides compounds and methods for inhibiting histone deacetylase enzymatic activity. The invention also provides compositions and methods for treating cell proliferative diseases and conditions.

  这项发明涉及抑制组蛋白去乙酰化酶。该发明提供了抑制组蛋白去乙酰化酶酶活性的化合物和方法。该发明还提供了治疗细胞增殖性疾病和症状的组合物和方法。
• Synthesis and antiparasitic and antifungal evaluation of 2′-arylsubstituted-1H,1′H-[2,5′]bisbenzimidazolyl-5-carboxamidines
  作者：Mehmet Alp、Hakan Göker、Reto Brun、Sulhiye Yıldız

  DOI：10.1016/j.ejmech.2008.10.003

  日期：2009.5

  A series of 2′-arylsubstituted-1H,1′H-[2,5′]-bisbenzimidazolyl-5-carboxamidines were prepared in a six-step process starting from 4-amino-3-nitrobenzonitrile. The antiparasitic activity against Trypanosoma brucei rhodesiense (T.b.r.), Plasmodium falciparum (P.f.), Leishmania donovani (L.d.) and Trypanosoma cruzi (T.c.) and antifungal activity against Candida albicans and Candida krusei were evaluated

  一系列2'-芳基取代-1 ħ，1' ħ - [2,5'] - bisbenzimidazolyl -5-甲脒在由4-氨基-3-硝基苄腈开始的6步骤的过程中制备。在体外评价了对布鲁氏锥虫（Tbr），恶性疟原虫（Pf），利什曼原虫多诺尼（Ld）和克鲁氏锥虫（Tc）的抗寄生虫活性以及对白色念珠菌和库氏假丝酵母的抗真菌活性。几种化合物显示出对Tbr和Pf的体外活性与白色念珠菌相比，其对Pf的活性优于氯喹。
• [EN] A PROCESS FOR THE SYNTHESIS OF BISBENZIMIDAZOLES AND ITS DERIVATIONS<br/>[FR] PROCESSUS DE SYNTHÈSE DE BISBENZIMIDAZOLES ET DE SES DÉRIVÉS
  申请人：UNIV DELHI

  公开号：WO2004063170A1

  公开（公告）日：2004-07-29

  A process for the synthesis of bisbenzimidazoles and its derivations comprising; (i) reacting 5 chloroaniline with zinc dust and acetic anhydride to produce 5 chloroacetanilide; (ii) reacting 5 chloroacetanilide with HN03 to produce 2-nitro-5-chloroacetanilide; (ix) adding sodium methoxide to 2-nitro-5-ch1oroaniline; (x) heating 2-nitro-5-chloroaniline, methyl piperazine, anhydrous K2CO3 and Dimethyl formamide at 100-120°C produce a mixture which is cooled by pouring ice and is filtered to obtain 5-(4'-methylpiperazin-1'-yl)-2-nitroaniline; (xi) treating 5-(4'-methylpiperazin-l'yl)-2-nitroaniline with Pd/C to produce 2-amino-4-(4'-methylpiperazin-1'-yl) aniline; (xii) refluxing a mixture of 2-amino-4-(4'-methylpiperazin-1'yl) aniline and ethyl-4-amino-3-nitrobenzenecarboximidate hydrochloride in presence of ethanol/glacial acetic acid to produce 4-[5'-(4'-methylpiperazin-1'-yl) 15 benzimidazol-2'-yl)-2-nitroaniline; (xiii) treating a solution of 4-[5'-(4'-methylpiperazin-1'-yi) benzimidazol-2'-yl)-2-nitroaniline with palladium on carbon to yield 2-amino-4-[5'-(4'-Methylpiperazin-1'-yl)benzimidazol-2'-yl]aniline; (xiv) heating 2-amino-4-[5'-(4'-Methylpiperazin-1'-yl)benzimidazol-2'-yl]aniline and 3-4-dimethoxy benzaldehyde using nitrobenzene as a solvent at 110-150°C to produce (DMA) i.e 5-(4-methylpiperazin-1-yl)-2-[2'-(3,4-dimethoxyphenyl)-5'-benzimidazolyl] benzimidazole; (ix) heating 2-amino-4-[5'-(4'-Methylpiperazin-1'-yl) benzimidazol-2'-YI] aniline and 5-Formyl-[3-methoxy-4-hydroxy benzimidazole] using nitrobenzene at 110°C to 150°C in presence of argon to produce (TBZ) i.e 5-(4-methylpiperazine-1-yl)-2-[2' (2'-(4-hydroxy-3methoxyphenyl)5'benzimidazolyl) -5'- benzimidazolyl] benzimidazole.

  一种合成双苯并咪唑及其衍生物的方法，包括：(i)将5-氯苯胺与锌粉和乙酸酐反应，生成5-氯乙酰苯胺；(ii)将5-氯乙酰苯胺与硝酸反应，生成2-硝基-5-氯乙酰苯胺；(ix)将甲醇钠加入2-硝基-5-氯苯胺；(x)将2-硝基-5-氯苯胺、甲基哌嗪、无水K2CO3和二甲基甲酰胺加热至100-120°C，冷却后加入冰并过滤，得到5-(4'-甲基哌嗪基)-2-硝基苯胺；(xi)用Pd/C处理5-(4'-甲基哌嗪基)-2-硝基苯胺，得到2-氨基-4-(4'-甲基哌嗪基)苯胺；(xii)在乙醇/冰乙酸存在下，回流2-氨基-4-(4'-甲基哌嗪基)苯胺和乙酰基-4-氨基-3-硝基苯甲酰胺混合物，生成4-[5'-(4'-甲基哌嗪基)-2-硝基苯胺；(xiii)用碳载钯处理4-[5'-(4'-甲基哌嗪基)-2-硝基苯胺的溶液，得到2-氨基-4-[5'-(4'-甲基哌嗪基)苯并咪唑-2-基]苯胺；(xiv)将2-氨基-4-[5'-(4'-甲基哌嗪基)苯并咪唑-2-基]苯胺和3-4-二甲氧基苯甲醛在110-150°C下用硝基苯作溶剂加热，生成(DMA)即5-(4-甲基哌嗪基)-2-[2'-(3,4-二甲氧基苯基)-5'-苯并咪唑基]苯并咪唑；(ix)将2-氨基-4-[5'-(4'-甲基哌嗪基)苯并咪唑-2-基]苯胺和5-甲酰基-[3-甲氧基-4-羟基苯并咪唑]在110°C至150°C下用硝基苯在氩气存在下加热，生成(TBZ)即5-(4-甲基哌嗪基)-2-[2'-(2'-(4-羟基-3-甲氧基苯基)-5'-苯并咪唑基)-5'-苯并咪唑基]苯并咪唑。
• Structure-In Vitro Activity Relationships of Pentamidine Analogues and Dication-Substituted Bis-Benzimidazoles as New Antifungal Agents
  作者：Maurizio Del Poeta、Wiley A. Schell、Christine C. Dykstra、Susan Jones、Richard R. Tidwell、Agnieszka Czarny、Miroslav Bajic、Marina Bajic、Arvind Kumar、David Boykin、John R. Perfect

  DOI：10.1128/aac.42.10.2495

  日期：1998.10

  Twenty analogues of pentamidine, 7 primary metabolites of pentamidine, and 30 dicationic substituted bis-benzimidazoles were screened for their inhibitory and fungicidal activities against Candida albicans and Cryptococcus neoformans . A majority of the compounds had MICs at which 80% of the strains were inhibited (MIC ₈₀ s) comparable to those of amphotericin B and fluconazole. Unlike fluconazole, many of these compounds were found to have potent fungicidal activity. The most potent compound against C. albicans had an MIC ₈₀ of ≤0.09 μg/ml, and the most potent compound against C. neoformans had an MIC ₈₀ of 0.19 μg/ml. Selected compounds were also found to be active against Aspergillus fumigatus , Fusarium solani , Candida species other than C. albicans , and fluconazole-resistant strains of C. albicans and C. neoformans . It is clear from the data presented here that further studies on the structure-activity relationships, mechanisms of action and toxicities, and in vivo efficacies of these compounds are warranted to determine their clinical potential.

  摘要：对于20种戊二胺类似物、7种戊二胺的主要代谢产物以及30种二阳离子取代的双苯并咪唑类化合物进行了筛选，评估它们对念珠菌和隐球菌的抑制和杀真菌活性。大多数化合物的MIC（80%菌株被抑制的最小抑菌浓度）与两性霉素B和氟康唑相当。与氟康唑不同，许多这些化合物表现出强效的杀真菌活性。对于念珠菌而言，最有效的化合物的MIC80为≤0.09μg/ml，对于隐球菌而言，最有效的化合物的MIC80为0.19μg/ml。选择的化合物也对曲霉、索兰镰孢霉、除念珠菌外的其他种类的念珠菌，以及氟康唑耐药菌株的活性。从这里呈现的数据清楚地表明，有必要进行进一步的研究，以确定这些化合物的结构活性关系、作用机制和毒性，以及它们在体内的疗效，以确定它们的临床潜力。