7-nitro-1,2-naphthoquinone

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 7-nitro-1,2-naphthoquinone
• 英文别名: 7-Nitro-[1,2]naphthoquinone；7-nitronaphthalene-1,2-dione
• 化学式: C₁₀H₅NO₄
• 分子量: 203.154
• InChiKey: CHGRLGUYJLNMEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  7-硝基-3,4-二氢-2H-1-萘酮 在 selenium(IV) oxide 作用下， 以 溶剂黄146 为溶剂， 反应 7.0h， 生成 7-nitro-1,2-naphthoquinone
  参考文献：
  名称：

  Novel Angular Benzophenazines:  Dual Topoisomerase I and Topoisomerase II Inhibitors as Potential Anticancer Agents

  摘要：

  A series of substituted angular benzophenazines were prepared using a new synthetic route via a novel regiocontrolled condensation of 1,2-naphthoquinones and 2,3-diaminobenzoic acids. The synthesis and biological activity of this new series of substituted 8,9-benzo[a]phenazine carboxamide systems are described. The analogues were evaluated against the H69 parental human small cell lung carcinoma cell line and H69/LX4 resistant cell line which overexpresses P-glycoprotein. Selected analogues were evaluated against the COR-L23-parental human non small cell lung carcinoma cell line and the COR-L23/R resistant cell line which overexpresses multidrug resistance protein. This series of novel angular benzophenazines were potent cytotoxic agents in these cell lines and may be able to circumvent multidrug resistance mechanisms which result in the lack of efficacy of many drugs in cancer chemotherapy. These compounds show dual inhibition of topoisomerase I and topoisomerase II and thus target two key enzymes responsible for the topology of DNA that are active at different points in the cell cycle. The introduction of chirality into the carboxamide side chain of these novel benzophenazine carboxamides has resulted in the discovery of a potent enantiospecific series of cytotoxic agents, exemplified by 4-methoxy-benzo[a]phenazine-11-carboxylic acid (2-(dimethylamino)-1-(R)methyl-ethyl)-amide, XR11576 ((R)-4j"). In vivo activity has been demonstrated for 4-methoxy-benzo[a]phenazine-11-carboxylic acid (2-(dimethylamino)-1-(R)-methyl-ethyl)-amide, XR11576, after intravenous administration to female mice, and this compound has been selected as a development candidate for further evaluation.

  DOI：

  10.1021/jm010329a

文献信息

• Benzo[A] [phenazin-11-carboxamide derivatives and their use as joint inhibitors of topomerase I and II
  申请人：——

  公开号：US20030139409A1

  公开（公告）日：2003-07-24

  A compound which is a benzo[a]phenazine-11-carboxamide derivative of formula (I) wherein each of R 1 to R 4 , which are the same or different, is selected from hydrogen, halogen, hydroxyl, C 1 -C 6 alkoxy which is unsubstituted or substituted, heteroaryloxy, C 1 -C 6 alkyl which is unsubstituted or substituted, nitro, cyano, azido, amidoxime, CO 2 R 10 , CON(R 12 ) 2 , OCON(R 12 ), SR 10 , SOR 11 , SO 2 (R 11 ), SO 2 N(R 12 ) 2 , N(R 12 ) 2 , NR 10 SO 2 R 11 , N(SO 2 R 11 ) 2 NR 10 (CH 2 ) n CN, NR 10 COR 11 , OCOR 11 or COR 10 ; each of R 5 to R 7 , which are the same or different, is selected from hydrogen, halogen, hydroxy, C 1 -C 6 alkoxy, C 1 -C 6 alkyl, SR 10 and N(R 12 ) 2 ; Q is C 1 -C 6 alkylene which is unsubstituted or substituted by (i) C 1 -C 6 alkyl which is unsubstituted or substituted, (ii) hydroxy, provided that the hydroxy group is not, to either of the N atoms adjacent to Q in formula (I), (iii) CO 2 R 10 , or (iv) CON(R 12 ); R 1 and R 9 , which are the same or different, are each hydrogen or C 1 -C 6 alkyl, or R 8 and R 9 together with the nitrogen atom to which they are attached form a saturated 5- or 6-membered N-containing heterocyclic ring which may include one additional heteroatom selected from O, N and S, or one of R 8 and R 9 is an alkylene chain optionally interrupted by O, N or S, which is attached to a carbon atom on the alkylene chain represented by Q to complete a saturated 5- or 6-membered N-containing heterocyclic ring as defined above; or a pharmaceutically acceptable salt thereof; with the proviso that at least one R 1 to R 4 is other than hydrogen. These compounds are inhibitors of topoisomerase I and/or topoisomerase II and can be used to treat tumours, including tumours which express MDR.

  一种化合物，是一种公式（I）的苯并[a]菲啉-11-甲酰胺衍生物，其中R1至R4中的每一个，它们相同或不同，被选择为氢、卤素、羟基、未取代或取代的C1-C6烷氧基、杂环氧基、未取代或取代的C1-C6烷基、硝基、氰基、叠氮基、酰肼基、CO2R10、CON(R12)2、OCON(R12)、SR10、SOR11、SO2(R11)、SO2N(R12)2、N(R12)2、NR10SO2R11、N(SO2R11)2NR10(CH2)nCN、NR10COR11、OCOR11或COR10；R5至R7中的每一个，它们相同或不同，被选择为氢、卤素、羟基、C1-C6烷氧基、C1-C6烷基、SR10和N(R12)2；Q是未取代或取代的C1-C6烷基，其被（i）未取代或取代的C1-C6烷基，（ii）羟基、前提是羟基不是在公式（I）中与Q相邻的任一N原子，（iii）CO2R10，或（iv）CON(R12)所取代；R1和R9，它们相同或不同，分别是氢或C1-C6烷基，或R8和R9连同它们连接到的氮原子形成饱和的5-或6-成员N-含杂环戊或六元环，可能包括一个额外的由O、N和S中选择的杂原子，或R8和R9中的一个是由O、N或S随机中断的烷基链，它连接到由Q表示的烷基链上的碳原子，以完成上述定义的饱和的5-或6-成员N-含杂环戊或六元环；或其药学上可接受的盐；但至少一个R1到R4不是氢。这些化合物是拓扑异构酶I和/或拓扑异构酶II的抑制剂，可用于治疗肿瘤，包括表达MDR的肿瘤。
• 1,2-Dihydro-1,2-dihydroxynaphthalene dehydrogenase containing recombinant strains: Preparation, isolation and characterisation of 1,2-dihydroxynaphthalenes and 1,2-naphthoquinones
  作者：Camilla Cavallotti、Fulvia Orsini、Guido Sello、Patrizia Di Gennaro、Enrica Galli、Giuseppina Bestetti

  DOI：10.1016/s0040-4020(99)00135-0

  日期：1999.4

  toxicity problem. Products are isolated and characterised as t-butyldimethylsilyl derivatives that are stable compounds. The transformation of the 1,2-dihydroxynaphthalenes into the corresponding 1,2-naphthoquinones is also reported.

  通过使用含有从荧光假单胞菌N3中克隆的二氢二醇萘脱氢酶基因的大肠杆菌重组菌株，通过将相应的1，2-二氢-1,2-二羟基萘脱氢来生产1,2-二羟基萘。在精心控制的条件下进行转化，以最大程度地减少产品聚合。使用弱碱性树脂的多步骤程序可以分离出大量的产品，从而解决了毒性问题。分离出产物并将其表征为稳定化合物的叔丁基二甲基甲硅烷基衍生物。还报道了1，2-二羟基萘向相应的1，2-萘醌的转化。
• Pharmaceutical compounds
  申请人：Milton John

  公开号：US20050143383A1

  公开（公告）日：2005-06-30

  A compound which is a benzo[a]phenazine-11-carboxamide derivative of formula (I) wherein each of R 1 to R 4 , which are the same or different, is selected from hydrogen, halogen, hydroxyl, C 1 -C 6 alkoxy which is unsubstituted or substituted, heteroaryloxy, C 1 -C 6 alkyl which is unsubstituted or substituted, nitro, cyano, azido, amidoxime, CO 2 R 10 , CON(R 12 ) 2 , OCON(R 12 ), SR 10 , SOR 11 , SO 2 R 11 , SO 2 N(R 12 ) 2 , N(R 2 ) 2 , NR 10 SO 2 R 11 , N(SO 2 R 11 ) 2 NR 10 (CH 2 ) n CN, NR 10 COR 11 , OCOR 11 or COR 10 ; each of R 5 to R 7 , which are the same or different, is selected from hydrogen, halogen, hydroxy, C 1 -C 6 alkoxy, C 1 -C 6 alkyl, SR 10 and N(R 12 ) 2 ; Q is C 1 -C 6 alkylene which is unsubstituted or substituted by (i) C 1 -C 6 alkyl which is unsubstituted or substituted, (II) hydroxy, provided that the hydroxy group is not α to either of the N atoms adjacent to Q in formula (I), (iii) CO 2 R 10 , or (iv) CON(R 12 ); R 8 and R 9 , which are the same or different, are each hydrogen or C 1 -C 6 alkyl, or R 8 and R 9 together with the nitrogen atom to which they are attached form a saturated 5- or 6-membered N-containing heterocyclic ring which may include one additional heteroatom selected from O, N and S, or one of R 8 and R 9 is an alkylene chain optionally interrupted by O, N or S, which is attached to a carbon atom on the alkylene chain represented by Q to complete a saturated 5- or 6-membered N-containing heterocyclic ring as defined above; R 10 is hydrogen, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, benzyl or phenyl; R 11 is C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, benzyl or phenyl; each R 12 , which are the same or different, is hydrogen, C 1 -C 6 alkyl cycloalkyl, benzyl or phenyl, or the two R 12 groups form, together with the nitrogen atom to which they are attached a 5- or 6-membered saturated N-containing heterocyclic ring which may include 1 or 2 additional heteroatoms selected from O, N and S; and n is 1, 2 or 3; or a pharmaceutically acceptable salt thereof; with the proviso that at least one of R 1 to R 4 is other than hydrogen. These compounds are inhibitors of topoisomerase I and/or topoisomerase II and can be used to treat tumours, including tumours which express MDR.

  化合物为公式（I）的苯并[a]菲噻嗪-11-羧酰胺衍生物，其中R1至R4中的每个基团，相同或不同，选自氢、卤素、羟基、未取代或取代的C1-C6烷氧基、杂环氧基、未取代或取代的C1-C6烷基、硝基、氰基、叠氮基、酰肟基、CO2R10、CON(R12)2、OCON(R12)、SR10、SOR11、SO2R11、SO2N(R12)2、N(R2)2、NR10SO2R11、N(SO2R11)2NR10(CH2)nCN、NR10COR11、OCOR11或COR10；R5至R7中的每个基团，相同或不同，选自氢、卤素、羟基、C1-C6烷氧基、C1-C6烷基、SR10和N(R12)2；Q为未取代或取代的C1-C6烷基，可以由(i)未取代或取代的C1-C6烷基，(ii)羟基，但羟基不在公式（I）中与相邻的N原子之一相邻，(iii)CO2R10，或(iv)CON(R12)取代；R8和R9，相同或不同，均为氢或C1-C6烷基，或者R8和R9与它们附着的氮原子一起形成饱和的5-或6-成员N-含杂环，其中可以包括来自O、N和S的一个额外的杂原子，或者R8和R9是由O、N或S随意中断的烷基链，它附着在由Q表示的烷基链上的碳原子上，以完成上述定义的饱和的5-或6-成员N-含杂环；R10为氢、C1-C6烷基、C3-C6环烷基、苄基或苯基；R11为C1-C6烷基、C3-C6环烷基、苄基或苯基；每个R12，相同或不同，为氢、C1-C6烷基环烷基、苄基或苯基，或两个R12基团与它们附着的氮原子一起形成一个5-或6-成员饱和N-含杂环，其中可以包括1或2个来自O、N和S的额外杂原子；n为1、2或3；或其药学上可接受的盐；但至少有一个R1至R4不是氢。这些化合物是拓扑异构酶I和/或拓扑异构酶II的抑制剂，可用于治疗肿瘤，包括表达MDR的肿瘤。
• Process for preparing modified diene polymer rubbers
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0270071A2

  公开（公告）日：1988-06-08

  A process for preparing modified diene polymer rubbers having an increased impact resilience and a reduced hardness at low temperatures and useful as rubber materials for automobile tires and other industries which comprises producing an alkali metal-containing conjugated diene polymer, and reacting the alkali metal-containing polymer with a modifier selected from the group consisting of a nitro compound, a phosphoryl chloride compound of the formula: wherein R¹ to R⁴ are independently an alkyl group, and an aminosilane compound of the formula: wherein R⁵ to R⁷ are independently an alkyl group or an alkoxyl group, R⁸ and R⁹ are independently an alkyl group, and n is an integer, said alkali metal-containing diene polymer being prepared by a living anionic polymerization using an alkali metal-­based catalyst or by an addition reaction of a diene polymer having conjugated diene units and an alkali metal-based catalyst in a hydrocarbon solvent. The modified diene polymers can be incorporated with usual rubber additives to provide rubber compositions for various purposes, and the cured products show an increased impact resilience and a reduced hardness at low temperatures.

  一种用于制备改性二烯聚合物橡胶的工艺，该橡胶在低温下具有更高的冲击回弹 性和更低的硬度，可用作汽车轮胎和其他工业的橡胶材料，该工艺包括制备含碱金属 的共轭二烯聚合物，并将该含碱金属聚合物与选自以下组别的改性剂反应：硝基化合物、 式中的磷酰氯化合物、式中的氨基硅烷化合物、式中的氨基硅烷化合物、式中的氨基硅烷 化合物： 式中 R¹ 至 R⁴ 独立地为烷基，以及式中氨基硅烷化合物： 其中 R⁵ 至 R⁷ 独立地为烷基或烷氧基，R⁸ 和 R𠞙 独立地为烷基，且 n 为整数、 所述含碱金属的二烯聚合物是通过使用碱金属基催化剂的活阴离子聚合反应或通过具有共轭二烯单元的二烯聚合物与碱金属基催化剂在烃溶剂中的加成反应制备的。改性二烯聚合物可与通常的橡胶添加剂结合，提供各种用途的橡胶组合物，固化产品在低温下显示出更高的冲击回弹性和更低的硬度。
• Modified diene polymer rubbers
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0341496A2

  公开（公告）日：1989-11-15

  A process for preparing modified diene polymer rubbers having an increased impact resilience, a reduced hardness at low temperatures and an improved processability, and useful as rubber materials for automobile tires and other industries which comprises producing a conjugated diene polymer having alkali metal end or ends, and reacting the alkali metal-containing polymer with (a) a silicon or tin compound of the formula: RaMXb wherein R is an alkyl group, an alkenyl group, a cycloalkenyl group or an aromatic hydrocarbon group, M is silicon atom or tin atom, X is a halogen atom, a is 0, 1 or 2 and b is 2, 3 or 4, and (b) at least one member selected from the group consisting of a nitro compound; a phosphoryl chloride compound of the formula (1): wherein R¹, R², R³ and R⁴ are an alkyl group; an aminosilane compound of the formula (2): wherein R⁵, R⁶ and R⁷ are an alkyl group or an alkoxyl group, R⁸ and R⁹ are an alkyl group, and n is an integer; an acrylamide compound of the formula (3): wherein R¹⁰ is hydrogen atom or methyl group, R¹¹ and R¹² are an alkyl group, and m is an integer; and an aminovinylsilane compound of the formula (4): where R¹³, R¹⁴, R¹⁵, R¹⁶ and R¹⁷ are an alkyl group.

  一种制备改性二烯聚合物橡胶的工艺，该橡胶具有更高的冲击回弹性、更低的低温硬度和更好的可加工性，可用作汽车轮胎和其他工业的橡胶材料，该工艺包括生产具有碱金属末端的共轭二烯聚合物，并使含碱金属的聚合物与(a)式中的硅或锡化合物反应：其中 R 为烷基、烯基、环烯基或芳香烃基，M 为硅原子或锡原子，X 为卤素原子，a 为 0、1 或 2，b 为 2、3 或 4，以及 (b) 至少一种选自以下组成的成员：硝基化合物；式 (1) 的磷酰氯化合物： 其中 R¹、R²、R³ 和 R⁴ 是烷基；式 (2) 的氨基硅烷化合物： 其中 R⁵、R⁶ 和 R⁷ 是烷基或烷氧基，R⁸ 和 R𠞙 是烷基，且 n 是整数；式（3）的丙烯酰胺化合物： 其中 R¹⁰ 是氢原子或甲基，R¹¹ 和 R¹² 是烷基，m 是整数；以及式（4）的氨基乙烯基硅烷化合物： 其中 R¹³、R¹⁴、R¹⁵、R¹⁶ 和 R¹⁷ 是烷基。