N-(3,5-dinitrobenzyl)phthalimide | 444343-45-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-(3,5-dinitrobenzyl)phthalimide
• 英文别名: 2-[(3,5-dinitrophenyl)methyl]isoindoline-1,3-dione；N-(3,5-dinitrophenyl)methylphthalimide；(1H)Isoindole-1,3(2H)-dione, 2-[(3,5-dinitrophenyl)methyl]-；2-[(3,5-dinitrophenyl)methyl]isoindole-1,3-dione
• CAS: 444343-45-7
• 化学式: C₁₅H₉N₃O₆
• 分子量: 327.253
• InChiKey: MYJQBBXXBLLTHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  129
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(3,5-dinitrobenzyl)phthalimide 在 对甲苯磺酸 、 肼 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 3,5-dinitrobenzylamine
  参考文献：
  名称：

  “无间隔的”二马来酰亚胺氟中的猝灭效率显着提高†

  摘要：

  在这个后基因组时代，需要新技术来应对将功能角色分配给大量已确定的推定基因产物的任务。我们基于合成的荧光探针试剂的使用，开发了一种极简主义的标记策略，该试剂仅在与目标肽序列反应后才发出荧光。探针试剂具有荧光核心并带有两个马来酰亚胺基团，因此它们的潜伏荧光通过光致电子转移（PET）到悬挂的马来酰亚胺基团而猝灭，直到这两个基团都进行了特定的硫醇加成反应。荧光猝灭的效率对于该标记方法的实用性至关重要，并且已被预测与荧光团和马来酰亚胺基团之间的分子内距离有关。我们已经通过制备一系列新颖的氟进行了该假设的首次直接检验，这些氟的区别仅在于将香豆素荧光团和二马来酰亚胺片段分开的间隔基部分。在与两个当量的硫醇反应后，观察到分子内距离与荧光增强（FE）之间存在惊人的相关性。在此观察结果的指导下，我们设计了“无间隔”的氟气，其中的丹磺酰基衍生物的FE比率> 300，这是二马来酰亚胺氟气的最大记录。本文观察到的趋

  DOI：

  10.1039/c0ob00455c
• 作为产物：
  描述：

  3,5-二硝基苯甲酸 在 sodium tetrahydroborate 、 偶氮二甲酸二异丙酯 、 三氟化硼乙醚 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 49.0h， 生成 N-(3,5-dinitrobenzyl)phthalimide
  参考文献：
  名称：

  “无间隔的”二马来酰亚胺氟中的猝灭效率显着提高†

  摘要：

  在这个后基因组时代，需要新技术来应对将功能角色分配给大量已确定的推定基因产物的任务。我们基于合成的荧光探针试剂的使用，开发了一种极简主义的标记策略，该试剂仅在与目标肽序列反应后才发出荧光。探针试剂具有荧光核心并带有两个马来酰亚胺基团，因此它们的潜伏荧光通过光致电子转移（PET）到悬挂的马来酰亚胺基团而猝灭，直到这两个基团都进行了特定的硫醇加成反应。荧光猝灭的效率对于该标记方法的实用性至关重要，并且已被预测与荧光团和马来酰亚胺基团之间的分子内距离有关。我们已经通过制备一系列新颖的氟进行了该假设的首次直接检验，这些氟的区别仅在于将香豆素荧光团和二马来酰亚胺片段分开的间隔基部分。在与两个当量的硫醇反应后，观察到分子内距离与荧光增强（FE）之间存在惊人的相关性。在此观察结果的指导下，我们设计了“无间隔”的氟气，其中的丹磺酰基衍生物的FE比率> 300，这是二马来酰亚胺氟气的最大记录。本文观察到的趋

  DOI：

  10.1039/c0ob00455c

文献信息

• Trisubstituted carbocyclic cyclophilin binding compounds and their use
  申请人：——

  公开号：US20020165275A1

  公开（公告）日：2002-11-07

  The present invention relates to novel, non-peptidic small organic compounds having an affinity for cyclophilin (CyP)-type immunophilin proteins, and to pharmaceutical compositions comprising one or more of the said compounds. The invention further relates to the uses of these compounds and compositions for binding CyP-type proteins, inhibiting their peptidyl-prolyl isomerase activity, and for research, development, and therapeutic applications in a variety of medical disorders.

  本发明涉及一种新型的非肽类小有机化合物，其具有与环肽亚精蛋白（CyP）型免疫蛋白亲和力，并且涉及包含所述化合物中的一个或多个的药物组合物。该发明还涉及这些化合物和组合物用于结合CyP型蛋白，抑制其肽基脯氨酸异构酶活性，并在各种医学疾病的研究、开发和治疗应用中的用途。
• Fluorescent markers and use thereof for labeling specific protein targets
  申请人：Keillor Jeffrey

  公开号：US08835641B2

  公开（公告）日：2014-09-16

  Novel fluorescent markers of Formula I: are disclosed herein, wherein X and Y are independently or together absent or are independently selected from R and R1 are independently selected from H and alkyl; Ar is phenyl or heteroaryl; L is absent or a spacer selected from the group consisting of —NH—; —(CH2)nNH—; —NHSO2—; —(CH2)nNHCO—; -(cycloalkyl)NHCO—; —(CH2)nNHSO2—; -(cycloalkyl)NHSO2—; —CONH(CH2)nNHCO—; —CONH(cycloalkyl)NHCO—; —NHCO(CH2)nNHCO—; —NHCO(cycloalkyl)NHCO—; —(CH2)nSO2NH—; -(cycloalkyl)SO2NH—; —(CH2)nNHCSNH—; -(cycloalkyl)NHCSNH—; —CR═CR1—; —C≡C—; —(CH2)nN═CH—; -(cycloalkyl)N═CH—; —N═CH(CH2)—; —N═CH(cycloalkyl)-; n is an integer ranging from 1 to 5; F is a fluorophore selected from the group consisting of fluorescein, rhodamine, eosin, thionine, safranin, coumarin, methoxycoumarin, dansyl, BODIPY and BODIPY derivatives; and wherein X, Y and L may be positioned in a 1,3,5; 1,2,3; 1,3,4 or in a 3,4,5 configuration respectively.

  本文披露了一种新颖的荧光标记物，其中X和Y可以独立或一起缺失，也可以分别选择自R和R1，R和R1可以分别选择自H和烷基；Ar为苯基或杂环芳基；L可以是缺失或从以下组中选择的间隔物，该组包括—NH—；—（CH2）nNH—；—NHSO2—；—（CH2）nNHCO—；-（环烷基）NHCO—；—（CH2）nNHSO2—；-（环烷基）NHSO2—；—CONH（CH2）nNHCO—；—CONH（环烷基）NHCO—；—NHCO（CH2）nNHCO—；—NHCO（环烷基）NHCO—；—（CH2）nSO2NH—；-（环烷基）SO2NH—；—（CH2）nNHCSNH—；-（环烷基）NHCSNH—；—CR═CR1—；—C≡C—；—（CH2）nN═CH—；-（环烷基）N═CH—；—N═CH（CH2）—；—N═CH（环烷基）-；n为1到5的整数；F为从荧光素、罗丹明、苏丹、亚甲基蓝、藏红、香豆素、甲氧基香豆素、丹磺酰基、BODIPY和BODIPY衍生物组中选择的荧光团；其中X、Y和L可以分别位于1,3,5；1,2,3；1,3,4或3,4,5配置中。
• FLUORESCENT MARKERS AND USE THEREOF FOR LABELING SPECIFIC PROTEIN TARGETS
  申请人：Keillor Jeffrey

  公开号：US20120171665A1

  公开（公告）日：2012-07-05

  Novel fluorescent markers of Formula I: are disclosed herein, wherein X and Y are independently or together absent or are independently selected from R and R 1 are independently selected from H and alkyl; Ar is phenyl or heteroaryl; L is absent or a spacer selected from the group consisting of —NH—; —(CH 2 ) n NH—; —NHSO 2 —; —(CH 2 ) n NHCO—; -(cycloalkyl)NHCO—; —(CH 2 ) n NHSO 2 —; -(cycloalkyl)NHSO 2 —; —CONH(CH 2 ) n NHCO—; —CONH(cycloalkyl)NHCO—; —NHCO(CH 2 ) n NHCO—; —NHCO(cycloalkyl)NHCO—; —(CH 2 ) n SO 2 NH—; -(cycloalkyl)SO 2 NH—; —(CH 2 ) n NHCSNH—; -(cycloalkyl)NHCSNH—; —CR═CR 1 —; —C≡C—; —(CH 2 ) n N═CH—; -(cycloalkyl)N═CH—; —N═CH(CH 2 )—; —N═CH(cycloalkyl)-; n is an integer ranging from 1 to 5; F is a fluorophore selected from the group consisting of fluorescein, rhodamine, eosin, thionine, safranin, coumarin, methoxycoumarin, dansyl, BODIPY and BODIPY derivatives; and wherein X, Y and L may be positioned in a 1,3,5; 1,2,3; 1,3,4 or in a 3,4,5 configuration respectively.

  本申请公开了Formula I的新型荧光标记物，其中X和Y可以独立地或共同缺席，也可以分别选自R和R1，R和R1分别选自H和烷基；Ar为苯基或杂环芳基；L可以是缺席或从—NH—；—(CH2)nNH—；—NHSO2—；—(CH2)nNHCO—；-(环烷基)NHCO—；—(CH2)nNHSO2—；-(环烷基)NHSO2—；—CONH(CH2)nNHCO—；—CONH(环烷基)NHCO—；—NHCO(CH2)nNHCO—；—NHCO(环烷基)NHCO—；—(CH2)nSO2NH—；-(环烷基)SO2NH—；—(CH2)nNHCSNH—；-(环烷基)NHCSNH—；—CR═CR1—；—C≡C—；—(CH2)nN═CH—；-(环烷基)N═CH—；—N═CH(CH2)—；—N═CH(环烷基)-；n为1到5的整数；F为从荧光素、罗丹明、苏丹、亚甲蓝、藏红花、香豆素、甲氧基香豆素、丹磺酰胺、BODIPY和BODIPY衍生物中选择的荧光团；X、Y和L可以分别位于1,3,5；1,2,3；1,3,4或3,4,5构型中。
• Development of 3,5-Dinitrophenyl-Containing 1,2,4-Triazoles and Their Trifluoromethyl Analogues as Highly Efficient Antitubercular Agents Inhibiting Decaprenylphosphoryl-β-<scp>d</scp>-ribofuranose 2′-Oxidase
  作者：Galina Karabanovich、Jan Dušek、Karin Savková、Oto Pavliš、Ivona Pávková、Jan Korábečný、Tomáš Kučera、Hana Kočová Vlčková、Stanislav Huszár、Zuzana Konyariková、Klára Konečná、Ondřej Jand’ourek、Jiřina Stolaříková、Jana Korduláková、Kateřina Vávrová、Petr Pávek、Věra Klimešová、Alexandr Hrabálek、Katarína Mikušová、Jaroslav Roh

  DOI：10.1021/acs.jmedchem.9b00912

  日期：2019.9.12

  We report herein the discovery of 3,5-dinitrophenyl 1,2,4-triazoles with excellent and selective antimycobacterial activities against Mycobacterium tuberculosis strains, including clinically isolated multidrug-resistant strains. Thorough structure activity relationship studies of 3,5-dinitrophenyl-containing 1,2,4-triazoles and their trifluoromethyl analogues revealed the key role of the position of the 3,5-dinitrophenyl fragment in the antitubercular efficiency. Among the prepared compounds, the highest in vitro antimycobacterial activities against M. tuberculosis H(37)Rv and against seven clinically isolated multidrug-resistant strains of M. tuberculosis were found with S-substituted 4-alkyl-5-(3,5-dinitrophenyl)-4H-1,2,4-triazole-3-thiols and their 3-nitro-5-(trifluoromethyl)phenyl analogues. The minimum inhibitory concentrations of these compounds reached 0.03 mu M, which is superior to all the current first-line anti-tuberculosis drugs. Furthermore, almost all compounds with excellent antimycobacterial activities exhibited very low in vitro cytotoxicities against two proliferating mammalian cell lines. The docking study indicated that these compounds acted as the inhibitors of decaprenylphosphoryl-beta-D-ribofuranose 2'-oxidase enzyme, which was experimentally confirmed by two independent radiolabeling experiments.
• TRISUBSTITUTED CARBOCYCLIC CYCLOPHILIN BINDING COMPOUNDS AND THEIR USE
  申请人：GUILFORD PHARMACEUTICALS INC.

  公开号：EP1360173A2

  公开（公告）日：2003-11-12