5-氟萘-1,2-二酮 | 62784-47-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 5-氟萘-1,2-二酮
• 英文名称: 5-fluoro-1,2-naphthoquinone
• 英文别名: 5-Fluoronaphthalene-1,2-dione
• CAS: 62784-47-8
• 化学式: C₁₀H₅FO₂
• mdl: MFCD18448417
• 分子量: 176.147
• InChiKey: SUISEZMMBHAFIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 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：
  34.1
• 氢给体数：
  0
• 氢受体数：
  3

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  5-氟-1-四氢萘酮	5-fluoro-3,4-dihydronaphthalen-1(2H)-one	93742-85-9	C10H9FO	164.179

反应信息

• 作为反应物：
  描述：

  5-氟萘-1,2-二酮 在 盐酸 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 6.0h， 生成 4-methylsulfanyl-benzo[a]phenazine-11-carboxylic acid
  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
• 作为产物：
  描述：

  5-氟-1-四氢萘酮 在 selenium(IV) oxide 作用下， 以 溶剂黄146 为溶剂， 反应 7.0h， 生成 5-氟萘-1,2-二酮
  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

• Oxidation with Fremy's salt—VIII
  作者：H. Ishii、T. Hanaoka、T. Asaka、Y. Harada、N. Ikeda

  DOI：10.1016/0040-4020(76)80108-1

  日期：1976.1

  It has been shown by a series of experiments on 5-alkyl, 5-halo-, and other 5-substituted 1-naphthol derivatives that the product ratio of the ortho- and para-naphthoquinones formed on oxidation with Fremy's salt is controlled by the bulkiness of the C5-substituent.

  在5-烷基，5-卤代和其他5-取代的1-萘酚衍生物上进行的一系列实验表明，用Fremy's盐氧化形成的邻萘和对萘萘醌的产物比率受C 5-取代基的体积大。
• Synthesis and biological activity of some known and putative duloxetine metabolites
  作者：F. Kuo、T.A. Gillespie、P. Kulanthaivel、R.J. Lantz、T.W. Ma、D.L. Nelson、P.G. Threlkeld、W.J. Wheeler、P. Yi、M. Zmijewski

  DOI：10.1016/j.bmcl.2004.04.066

  日期：2004.7

  Several putative phase I duloxetine metabolites, 4-hydroxy-, 5-hydroxy-, 6-hydroxy-, 5-hydroxy-6-methoxy-, 6-hydroxy5-methoxy-, 5,6-dihydroxy-, and 4,6-dihydroxyduloxetine were synthesized, and their phase II metabolite as glucuronide or sulfate conjugates were also synthesized. Their in vitro binding activities were compared to that of parent compound duloxetine. (C) 2004 Elsevier Ltd. All rights reserved.
• ISHII H.; HANAOKA T.; ASAKA T.; HARADA Y.; IKEDA N., TETRAHEDRON, 1976, NO 32, 2693-2698
  作者：ISHII H.、 HANAOKA T.、 ASAKA T.、 HARADA Y.、 IKEDA N.

  DOI：——

  日期：——
• UTILISATION DE DERIVES DE TETRACYCLES MONO OU DICETONIQUES, NOUVEAUX COMPOSES OBTENUS ET LEUR APPLICATION EN THERAPEUTIQUE
  申请人：LABORATOIRE INNOTHERA Société Anonyme

  公开号：EP0876368A1

  公开（公告）日：1998-11-11
• [EN] USE OF MONO- OR DIKETONE TETRACYCLIC DERIVATIVES, RESULTING NOVEL COMPOUNDS AND THERAPEUTICAL USE THEREOF<br/>[FR] UTILISATION DE DERIVES DE TETRACYCLES MONO OU DICETONIQUES, NOUVEAUX COMPOSES OBTENUS ET LEUR APPLICATION EN THERAPEUTIQUE
  申请人：LABORATOIRE INNOTHERA

  公开号：WO1997021709A1

  公开（公告）日：1997-06-19

  (EN) The therapeutical use of tetracyclic derivatives and pharmaceutically acceptable salts thereof having general formula (I), for treating diseases related to venous function deficiency and/or inflammatory oedema, is disclosed. In general formula (I), X is a carbon atom or a nitrogen atom; T is a carbon atom or a nitrogen atom; L is an oxygen atom or a ketone function protecting grouping; R1 is a hydrogen atom, a halogen atom or a C1-5 alkyl radical; R2 is a hydrogen atom, a halogen atom, a nitro radical or a C1-5 alkyl radical; and n and m are 0 or 1 but not independently so, whereby when n is 1 then m is 0, and vice versa.(FR) L'invention concerne l'utilisation en thérapeutique pour le traitement de maladies liées à une altération de la fonction veineuse et/ou à l'oedème inflammatoire de dérivés tétracycliques et de leurs sels acceptables du point de vue pharmaceutique répondant à la formule générale (I) dans laquelle indépendamment les uns des autres: X est un atome de carbone ou un atome d'azote, T est un atome de carbone ou un atome d'azote, L est un atome d'oxygène ou un groupement protecteur des fonctions cétoniques, R1 est un a tome d'hydrogène, un atome d'halogène, un radical alkyle en C1 à C5, R2 est un atome d'hydrogène, un atome d'halogène, un radical nitro, un radical alkyle en C1 à C5, n et m sont soit égaux à 0 soit à 1, mais non indépendamment l'un de l'autre de telle sorte que si n est égal à 1 alors m est égal à 0, et si n est égal à 0 alors m est égal à 1.