2-氯-3-硝基-5-(三氟甲基)苯甲酰胺 | 22227-47-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-氯-3-硝基-5-(三氟甲基)苯甲酰胺
• 英文名称: 2-chloro-3-nitro-5-(trifluoromethyl)benzamide
• 英文别名: 2-chloro-5-(trifluoromethyl)-3-nitrobenzamide
• CAS: 22227-47-0
• 化学式: C₈H₄ClF₃N₂O₃
• 分子量: 268.58
• InChiKey: VJMGWMDITIICJK-UHFFFAOYSA-N

物化性质

• 沸点：
  254.4±40.0 °C(Predicted)
• 密度：
  1.623±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  88.9
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  | 室温 |

反应信息

• 作为反应物：
  描述：

  2-氯-3-硝基-5-(三氟甲基)苯甲酰胺 在 三乙胺 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 生成 2-[(3-(methoxyimino)azetidin-1-yl)]-6-trifluoromethyl-8-nitryl-4H-benzo[e][1,3]thiazin-4-one
  参考文献：
  名称：

  Design, synthesis and antitubercular evaluation of benzothiazinones containing an oximido or amino nitrogen heterocycle moiety

  摘要：

  一系列具有氧肟基或氨基氮杂环基团的8-硝基-6-(三氟甲基)-1,3-苯并噻嗪-4-酮（BTZs），通过对BTZ043和BPTZ169的C-2位置进行改造设计和合成，作为新的抗结核药剂。

  DOI：

  10.1039/c6ra25712g
• 作为产物：
  描述：

  2-氯-3-硝基-5-(三氟甲基)苯甲酸 在 ammonium hydroxide 、 氯化亚砜 作用下， 以76%的产率得到2-氯-3-硝基-5-(三氟甲基)苯甲酰胺
  参考文献：
  名称：

  Design, synthesis and antitubercular evaluation of benzothiazinones containing an oximido or amino nitrogen heterocycle moiety

  摘要：

  一系列具有氧肟基或氨基氮杂环基团的8-硝基-6-(三氟甲基)-1,3-苯并噻嗪-4-酮（BTZs），通过对BTZ043和BPTZ169的C-2位置进行改造设计和合成，作为新的抗结核药剂。

  DOI：

  10.1039/c6ra25712g

文献信息

• [EN] BENZOTHIAZINONE DERIVATIVES AS ANTI -TUBERCULOSIS AGENTS<br/>[FR] DÉRIVÉS DE BENZOTHIAZINONE EN TANT QU'AGENTS ANTITUBERCULEUX
  申请人：UNIV QUEENSLAND

  公开号：WO2013038259A1

  公开（公告）日：2013-03-21

  Novel benzothiazinone derivatives of formula (I) or pharmaceutically acceptable salts or solvates thereof have been found to be effective against Mycobacterium tuberculosis strains and may thus be useful in the treatment of tuberculosis: wherein EWG (electron withdrawing group) = NO2, CN, CF3, F, Cl, Br, OCF3, OH, OR, OCHF2, COOR, wherein R is hydrogen or a straight or branched C1-C4 alkyl group, X = a bond or a straight or branched C1-C4 alkylene group which may be substituted with a group selected from F, Cl, Br, I or C1-C4 alkoxy; Y = hydrogen, a straight or branched C1-C4 alkyl group, OH or OR, wherein R is hydrogen or a straight or branched C1-C4 alkyl group; n = 0, 1 or 2; R1, R2 = hydrogen or substituent (s) which may be the same or different from each other and are selected from the group consisting of D, F, Cl, Br, CF3, a straight or branched C1-C4 alkyl group, a phenyl group, OR, SR, NR3R4, wherein R, R3, R4 may be the same or different from each other and are hydrogen or a straight or branched C1-C4 alkyl group or a phenyl group.

  化合物(I)的新型苯硫唑酮衍生物或其药学上可接受的盐或溶剂已被发现对结核分枝杆菌菌株具有有效性，因此可能在结核病的治疗中有用：其中EWG（电子提取基团）=NO2、CN、CF3、F、Cl、Br、OCF3、OH、OR、OCHF2、COOR，其中R为氢或直链或支链的C1-C4烷基基团，X=键或直链或支链的C1-C4烷基烃基团，可被来自F、Cl、Br、I或C1-C4烷氧基的基团取代；Y=氢、直链或支链的C1-C4烷基基团、OH或OR，其中R为氢或直链或支链的C1-C4烷基基团；n=0、1或2；R1、R2=氢或取代基（s），可以相同也可以不同，选自D、F、Cl、Br、CF3、直链或支链的C1-C4烷基基团、苯基、OR、SR、NR3R4，其中R、R3、R4可以相同也可以不同，为氢或直链或支链的C1-C4烷基基团或苯基。
• Benzothiazinone compounds and their use as anti-tuberculosis agents
  申请人：The University of Queensland

  公开号：EP2468746A1

  公开（公告）日：2012-06-27

  Novel benzothiazinone derivatives of formula (I) or a pharmaceutically acceptable salt or solvate thereof have been found to be effective against Mycobacterium tuberculosis strains and may thus be useful in the treatment of tuberculosis: wherein EWG (electron withdrawing group) = NO2, CN, CF3, F, Cl, Br, OCF3, OH, OR, OCHF2, COOR, wherein R is hydrogen, or a straight or branched C1-C4 alkyl group, X a bond, or a straight or branched C1-C4 alkylene group; Y = a bond, or a straight or branched C1-C4 alkylene group; wherein either one of X or Y is a bond and the other is a C1-C4- alkylene group, Z = N or C, n = 1 or 2; R1 = hydrogen, a straight or branched C1-C6 alkyl group, or a C3-C6 cycloalkyl group, which may be substituted with a group selected from F, Cl, Br, I or a C1-C4 alkoxy ; R2 = a phenyl group, a naphthyl group or a thienyl group, each of which may be unsubstituted or substituted with one or more substituent(s) which may be the same or different from each other, selected from the group consisting of F, Cl, Br, I, CN, NO2, or a straight or branched C1-C6 alkyl or phenyl group, which may be substituted with a group selected from F, Cl, Br, I, or C1-C4 alkoxy.

  化合物（I）的新型苯并噻唑酮衍生物或其药学上可接受的盐或溶剂已被发现对结核分枝杆菌菌株有效，并因此可能在结核病治疗中有用：其中EWG（电子提取基团）= NO2、CN、CF3、F、Cl、Br、OCF3、OH、OR、OCHF2、COOR，其中R为氢，或直链或支链C1-C4烷基；X为键，或直链或支链C1-C4亚烷基；Y = 键，或直链或支链C1-C4亚烷基；其中X或Y中的一个为键，另一个为C1-C4亚烷基，Z = N或C，n = 1或2；R1 = 氢，直链或支链C1-C6烷基，或C3-C6环烷基，可用F、Cl、Br、I或C1-C4烷氧基中选择的基团取代；R2 = 苯基，萘基或噻吩基，每个基团可以未取代或取代一个或多个取代基（s），其可相同或不同于来自F、Cl、Br、I、CN、NO2或直链或支链C1-C6烷基或苯基的基团，可用F、Cl、Br、I或C1-C4烷氧基中选择的基团取代。
• [EN] NOVEL ANTI-TUBERCULOSIS AGENTS<br/>[FR] NOUVEAUX AGENTS ANTI-TUBERCULOSE
  申请人：UNIV QUEENSLAND

  公开号：WO2012085654A1

  公开（公告）日：2012-06-28

  Novel benzothiazinone derivatives of formula (I) or a pharmaceutically acceptable salt or solvate thereof have been found to be effective against Mycobacterium tuberculosis strains and may thus be useful in the treatment of tuberculosis (I) wherein, EWG (electron withdrawing group) = N02, CN, CF3, F, CI, Br, OCF3, OH, OR, OCHF2, COOR, wherein R is hydrogen, or a straight or branched C1-C4 alkyl group, X = a bond, or a straight or branched C1-C4 alkylene group; Y = a bond, or a straight or branched C1-C4 alkylene group; wherein either one of X or Y is a bond and the other is a Ci-C4-alkylene group, Z = N or C, n = 1 or 2; R1 = hydrogen, a straight or branched C1-C6 alkyl group, or a C3-C6 cycloalkyl group, which may be substituted with a group selected from F, CI, Br, I or a C1-C4 alkoxy; R2 = a phenyl group, a naphthyl group or a thienyl group, each of which may be unsubstituted or substituted with one or more substituent(s) which may be the same or different from each other, selected from the group consisting of F, CI, Br, I, CN, NO2, or a straight or branched C1-C6 alkyl or phenyl group, which may be substituted with a group selected from F, CI, Br, I, or C1-C4 alkoxy.

  化合物的新型苯并噻唑酮衍生物（I）或其药学上可接受的盐或溶剂已被发现对结核分枝杆菌株具有有效作用，因此可能在结核病的治疗中有用（I）其中，EWG（电子吸引基团）= N02、CN、CF3、F、CI、Br、OCF3、OH、OR、OCHF2、COOR，其中R为氢，或直链或支链的C1-C4烷基基团，X = 一个键，或者是一个直链或支链的C1-C4烷基烃基团；Y = 一个键，或者是一个直链或支链的C1-C4烷基烃基团；其中X或Y中的任一者是一个键，另一个是一个Ci-C4-烷基烃基团，Z = N或C，n = 1或2；R1 = 氢，一个直链或支链的C1-C6烷基基团，或一个C3-C6环烷基团，它可以被来自F、CI、Br、I或C1-C4烷氧的基团取代；R2 = 苯基、萘基或噻吩基，每个基团可以未取代或取代一个或多个取代基，这些基团可以相同或不同于彼此，选自F、CI、Br、I、CN、NO2或直链或支链的C1-C6烷基或苯基基团，它可以被来自F、CI、Br、I或C1-C4烷氧的基团取代。
• 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。
• Macozinone: revised synthesis and crystal structure of a promising new drug for treating drug-sensitive and drug-resistant tuberculosis
  作者：Gang Zhang、Courtney C. Aldrich

  DOI：10.1107/s2053229619009185

  日期：2019.8.1

  Mycobacterium tuberculosis (Mtb), the principal etiological agent of tuberculosis (TB), infects over one-quarter of humanity and is now the leading cause of infectious disease mortality by a single pathogen. Macozinone 2-[4-(cyclohexylmethyl)piperazin-1-yl]-8-nitro-6-(trifluoromethyl)-4H-1,3-benzothiazin-4-one, C₂₀H₂₃F₃N₄O₃S} is a promising new drug for treating drug-sensitive and drug-resistant TB that has successfully completed phase I clinical trials. We report the complete spectroscopic and structural characterization by ¹H NMR, ¹³C NMR, HRMS, IR, and X-ray crystallography. The cyclohexyl moiety is observed to be nearly perpendicular to the core formed by the 1,3-benzothiazin-4-one and piperazine groups. The central piperazine ring adopts a slightly distorted chair conformation caused by sp ²-hybridization of the nitro N atom, which donates into the electron-deficient 1,3-benzothiazin-4-one group.

  结核分枝杆菌（Mtb）是结核病（TB）的主要病原体，感染了超过四分之一的人口，目前是单一病原体导致传染病死亡的主要原因。麦考嗪酮2-[4-(环己基甲基)哌嗪-1-基]-8-硝基-6-(三氟甲基)-4H-1,3-苯并噻嗪-4-酮，C20H23F3N4O3S}是一种治疗对药物敏感和耐药结核病的有前途的新药，已成功完成了 I 期临床试验。我们报告了通过 1H NMR、13C NMR、HRMS、IR 和 X 射线晶体学进行的完整光谱和结构表征。据观察，环己基与 1,3-苯并噻嗪-4-酮和哌嗪基团形成的核心几乎垂直。中央的哌嗪环由于硝基的 sp 硝基 N 原子的 sp2 杂化作用，使其捐献给缺电子的 1,3-苯并噻嗪-4-酮基团，从而使哌嗪环的中心呈现出略微扭曲的椅状构象。