2-chloro-3,5-dinitrobenzamide | 6266-51-9

• 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-chloro-3,5-dinitrobenzamide
• 英文别名: 2-Chlor-3,5-dinitrobenzamid
• CAS: 6266-51-9
• 化学式: C₇H₄ClN₃O₅
• mdl: MFCD00458647
• 分子量: 245.579
• InChiKey: GUDFEGXIJXTNJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  135
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-chloro-3,5-dinitrobenzamide 在 三氯氧磷 作用下， 以 (2S)-N-methyl-1-phenylpropan-2-amine hydrate 为溶剂， 生成 2-氯-3,5-二硝基苯甲腈
  参考文献：
  名称：

  Cyano phenylene dioxamic molecules

  摘要：

  下面代表的化合物##SPC1##及其制药组合物，其中包括非取代苯二酰氧胺，在对过敏反应和变态反应进行预防性治疗的敏感哺乳动物中是有用的，无论是由抗原或非抗原介导的自然。

  公开号：

  US03993679A1
• 作为产物：
  描述：

  2-氯-3,5-二硝基苯甲酸 在 ammonium hydroxide 、 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 丙酮 为溶剂， 反应 5.0h， 生成 2-chloro-3,5-dinitrobenzamide
  参考文献：
  名称：

  Hypoxia-Selective Antitumor Agents. 14. Synthesis and Hypoxic Cell Cytotoxicity of Regioisomers of the Hypoxia-Selective Cytotoxin 5-[N,N-Bis(2-chloroethyl)amino]-2,4-dinitrobenzamide

  摘要：

  A series of regioisomers of the novel hypoxia-selective cytotoxin (HSC) 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrabepzamide (2a) have been prepared by displacement of the chloro group from methyl chlorodinitrobenzoates or the corresponding carboxamides with diethanolamine, followed by dimesylation and mesylate displacement with LiCl. The compounds fall into two classes, where the two nitro groups have either a meta or an ortho (or para) disposition to each other. The four meta derivatives had one-electron reduction potentials in the range -340 to -375 mV, similar to that of the known isomer 2a, while the other isomers had much higher values (-262 to -285 mV). The meta derivatives were much less cytotoxic to AA8 cells under aerobic conditions (IC(50)s from 75 to 470 mu M) than were the other compounds (IC(50)s from 1.6 to 20 mu M). However, the ratios of IC(50)s Of the compounds in repair-proficient (AA8) and repair-deficient (UV4) cell lines varied, indicating differing contributions of DNA alkylation to aerobic toxicity between the isomers, with no clear relationship between this and nitro group disposition. The hypoxic selectivities of the (dimethylamino)ethylcarboxamide analogues for each isomer were determined by clonogenic assay against both AA8 and UV4 cells. With one exception, the meta derivatives showed excellent hypoxic selectivities (ca. 45-115-fold) against UV4 cells, while the ortho or para isomers had little selectivity (ca. 2-7-fold). A possible reason may be that the latter compounds, with higher reduction potentials, undergo rapid bioreduction even under aerobic conditions. None showed hypoxic selectivities greater than 2-3-fold against AA8 cells. The 3-[N,N-bis(2-chloroethyl)amino]-2,6-dinitrobenzamide isomer (5b), which showed the highest hypoxic selectivity for UV4 cells in this series, was active against both hypoxic and aerobic cells in KHT tumors in mice at well-tolerated doses, and showed superior in vivo activity to the previously studied 2,4-dinitro isomer 2b.

  DOI：

  10.1021/jm960057p

文献信息

• Mustard Prodrugs for Activation by<i> Escherichia coli</i> Nitroreductase in Gene-Directed Enzyme Prodrug Therapy
  作者：Frank Friedlos、William A. Denny、Brian D. Palmer、Caroline J. Springer

  DOI：10.1021/jm960794l

  日期：1997.4.1

  Twenty nitrogen mustard analogues derived from 5-(aziridin-1-yl)-2,4-dinitrobenzamide (CB 1954, 1) were evaluated as candidate prodrugs for gene-directed enzyme prodrug therapy (GDEPT) in Chinese hamster V79 cell lines engineered to express Escherichia coli nitroreductase (NR). Structural variations within the series included the use of N-dihydroxypropyl and (N-dimethylamino)ethyl carboxamide side

  在中国仓鼠V79细胞株中，将20种衍生自5-（叠氮基-1-基）-2,4-二硝基苯甲酰胺的氮芥类类似物（CB 1954，1）评估为基因定向酶前药治疗（GDEPT）的候选前药。表达大肠杆菌硝基还原酶（NR）。该系列中的结构变化包括使用N-二羟丙基和（N-二甲基氨基）乙基羧酰胺侧链，使用芥末上的氯，溴，甲磺酰基和碘代离去基团，以及区域异构变化。用表达NR的细胞和不表达NR的细胞系作为对照，测定化合物的细胞毒性（IC50）。混合物中非表达细胞经历其50％的细胞毒性（称为TE50）所需的NR表达细胞的比例用于评估化合物诱导旁观者效应的能力。
• Nitrophenylaziridine compounds and their use as prodrugs
  申请人：Auckland Uniservices Limited

  公开号：US06517836B1

  公开（公告）日：2003-02-11

  A range of aziridin-1-yl nitrobenzamides are provided for use as prodrugs in conjunction with nitroreductase (NR) enzymes. The amides may have 1 or 2-substituents which may be bulky and polar. For example, 5-(aziridin-1-yl)-N-[2-(4-morpholino)ethyl]-2,4-dinitrobenzamide of Formula (A) was found to be highly active against all NR+ cell lines tested.

  提供了一系列的环氧乙烷-1-基硝基苯酰胺作为前药，与硝基还原酶（NR）酶一起使用。这些酰胺可能具有1个或2个取代基，这些取代基可能是庞大且极性的。例如，发现Formula（A）的5-(环氧乙烷-1-基)-N-[2-(4-吗啉基)乙基]-2,4-二硝基苯酰胺对所有经过测试的NR+细胞系具有很高的活性。
• Dithiocarbamate derivatives and their use as antibacterial agents
  申请人：MEDAC GmbH

  公开号：EP1312607A1

  公开（公告）日：2003-05-21

  Compounds of the formula I wherein X is a bivalent residue selected from the group consisting of have excellent antibacterial activities and are useful agents for the therapeutic or prophylactic treatment of infectious diseases in mammals (humans and animals) caused by bacteria, especially diseases like tuberculosis (TB) and lepra caused by mycobacteria and infectious diseases caused by staphylococci.

  式I的化合物，其中X是从所述群组中选择的二价残基，具有出色的抗菌活性，并且是治疗或预防哺乳动物（人类和动物）由细菌引起的传染病的有用药剂，特别是由分枝杆菌引起的肺结核（TB）和麻风病以及由葡萄球菌引起的传染病。
• Transformations of ortho-methoxyaryl(hetaryl)carboxamides into quinazolin-4-one and pyrido[2,3-d]pyrimidin-4-one derivatives
  作者：O. B. Ryabova、V. A. Makarov、L. M. Alekseeva、A. S. Shashkov、V. V. Chernyshev、V. G. Granik

  DOI：10.1007/s11172-006-0057-x

  日期：2005.8

  undergo condensation accompanied by the pyrimidine ring closure on refluxing in an excess of sodium methoxide to form bicyclic products, viz., quinazolin-4-one, pyrido[2,3-d]pyrimidin-4-one, and pyrido[4,3-d]pyrimidin-4-one derivatives. The scheme of cyclization processes was proposed. The structures of the reaction products were confirmed by a number of physicochemical data, including X-ray diffraction

  摘要在环的 3 位和/或 5 位含有一个或两个硝基的邻氯芳基（杂芳基）甲酰胺在过量甲醇钠回流时缩合伴随嘧啶环闭合形成双环产物，即喹唑啉-4 -one、pyrido[2,3-d]pyrimidin-4-one 和pyrido[4,3-d]pyrimidin-4-one 衍生物。提出了环化工艺方案。反应产物的结构由许多物理化学数据证实，包括 X 射线衍射分析。
• New antimicrobial compounds, their synthesis and their use for treatment of mammalian infection
  申请人：Leibniz-Institut für Naturstoff-Forschung und Infektionsbiologie e.V. Hans-Knöll-Institut

  公开号：EP2020406A1

  公开（公告）日：2009-02-04

  The present invention relates to new antimicrobial compounds, their synthesis and their use for treatment of mammalian infections The present invention aims at the generation of new compounds with activity against mycobacteria as potential new tuberculosis drugs to overcome problems concerning resistance and drug intolerance. This aim has been solved by providing compounds of the formula I wherein R1 and R2 are, independently of each other, NO2, NR7R8, NHOR9, COOR9, CN, CONR10R11, CHO, F, Cl, Br, SO2NR12R13, lower alkoxy, OCF3, mono-, di or trifluoromethyl; R3 and R4 are, independently of each other, H, a saturated or unsaturated, linear or branched aliphatic radical having 1-3 chain members, F, Cl, Br, lower alkoxy; R5 is H, a saturated or unsaturated, halogenated or unhalogenated, linear or branched aliphatic radical having 1-7 chain members; R6 is a radical: wherein X is saturated or unsaturated, halogenated or unhalogenated, linear or branched aliphatic radical having 1-5 chain members, or R5 and R6 together represent bivalent radicals wherein n is 1-4: R7 - R13 are, independently of each other H or a saturated or unsaturated, halogenated or unhalogenated, linear or branched aliphatic radical having 1-5 chain members, phenyl, benzyl or R7 and R8 together, R10 and R11 together, R12 and R13 together represent a linear or branched aliphatic bivalent radical having 1-7 chain members; R14 and R15 are, independently of each other, H, linear or branched aliphatic radical having 1-5 chain members, F, Cl, Br, NO2, NH2, CF3.

  本发明涉及新的抗菌化合物，它们的合成以及它们用于治疗哺乳动物感染的用途。本发明旨在生成具有对抗结核分枝杆菌活性的新化合物，作为潜在的新结核病药物，以克服有关耐药性和药物不耐受性的问题。这一目标已通过提供具有以下结构的化合物来实现：其中R1和R2独立于彼此，为NO2、NR7R8、NHOR9、COOR9、CN、CONR10R11、CHO、F、Cl、Br、SO2NR12R13、低碳醇基、OCF3、单氟、二氟或三氟甲基；R3和R4独立于彼此，为H、具有1-3个链成员的饱和或不饱和、线性或支链脂肪基、F、Cl、Br、低碳醇基；R5为H、具有1-7个链成员的饱和或不饱和、卤代或非卤代、线性或支链脂肪基；R6为一个基团：其中X为具有1-5个链成员的饱和或不饱和、卤代或非卤代、线性或支链脂肪基，或R5和R6一起代表n为1-4的二价基团；R7-R13独立于彼此，为H或具有1-5个链成员的饱和或不饱和、卤代或非卤代、线性或支链脂肪基、苯基、苄基或R7和R8一起、R10和R11一起、R12和R13一起代表具有1-7个链成员的线性或支链脂肪双价基团；R14和R15独立于彼此，为H、具有1-5个链成员的线性或支链脂肪基、F、Cl、Br、NO2、NH2、CF3。