4-nitro-N-(2,2,6,6-tetramethylpiperidin-4-yl)-1,8-naphthalimide | 478309-30-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-nitro-N-(2,2,6,6-tetramethylpiperidin-4-yl)-1,8-naphthalimide
• 英文别名: 2,3-dihydro-2-(2,2,6,6-tetramethylpiperidin-4-yl)-6-nitro-1H-benz[de]isoquinoline-1,3-dione；6-nitro-2-(2,2,6,6-tetramethylpiperidin-4-yl)benzo[de]isoquinoline-1,3-dione
• CAS: 478309-30-7
• 化学式: C₂₁H₂₃N₃O₄
• 分子量: 381.431
• InChiKey: DADZBUCBSFBQSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  95.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-nitro-N-(2,2,6,6-tetramethylpiperidin-4-yl)-1,8-naphthalimide 生成 6-amino-2,3-dihydro-2-(2,2,6,6-tetramethylpiperidin-4-yl)-1H-benz[de]isoquinoline-1,3-dione hydrochloride
  参考文献：
  名称：

  Tricyclic compounds acting at serotonin receptor subtypes

  摘要：

  化合物的化学式I：##STR1## 其中Z为CH.sub.2或C.dbd.O；X和Y分别选自氢、卤素、羟基、低烷氧基、低烷基、硝基、氨基、氨基甲酰、(低烷基)氨基、二(低烷基)氨基和(低脂肪酰)氨基；R.sup.1为从式(a)、(b)、(c)、(d)和(e)中选择的基团：##STR2## 其中p为0或1；n为1、2或3；R.sup.2为氢、低烷基、C.sub.3-8环烷基、C.sub.3-8环烷基-C.sub.12烷基，或R.sup.6-C.sub.1-2烷基，其中R.sup.6为噻吩基、吡咯基或呋喃基，可选择地被一个或两个选自低烷基、低烷氧基、三氟甲基或卤素的取代基取代，或者为苯基，可选择地被一个或两个选自C.sub.1-4烷氧基、三氟甲基、卤素、硝基、羧基、酯化羧基和C.sub.1-4烷基的取代基取代，可选择地进一步被羟基、C.sub.1-4烷氧基、羧基、酯化羧基或体内可水解的酰氧基取代；每个R.sup.3独立地选自氢、羟基、烷基和烷氧基；每个R.sup.4独立地选自氢或烷基；R.sup.5为氢、低烷基、C.sub.3-8环烷基、C.sub.3-8环烷基-C.sub.1-2烷基、烯基、炔基或R.sup.7-C.sub.1-3烷基，其中R.sup.7为苯基或苯氧基，可选择地被一个或两个选自C.sub.1-4烷氧基、三氟甲基、卤素、硝基、羧基、酯化羧基和C.sub.1-4烷基的取代基取代，可选择地进一步被羟基、C.sub.1-4烷氧基、羧基、酯化羧基或体内可水解的酰氧基取代；以及其药学上可接受的盐、单体异构体、异构体混合物、制备方法、组合物和使用方法。

  公开号：

  US05202318A1
• 作为产物：
  描述：

  苊 在 potassium dichromate 、 硝酸 作用下， 以 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 16.5h， 生成 4-nitro-N-(2,2,6,6-tetramethylpiperidin-4-yl)-1,8-naphthalimide
  参考文献：
  名称：

  Design, photochemistry and antibacterial evaluation of novel light-harvesting antenna

  摘要：

  Novel light-harvesting compound6,based on 1,8-naphthalimide donors and perylenediimide acceptor were synthesized. The light-harvesting compound6showed intensive absorption band in range between 390 and 560 nm, that is 50 nm wider in comparison with the absorption of the model perylene dye. The novel antenna6has a higher ability to collect photons from environment in comparison with the single perylene diimide dyes. The chosen fluorophore units are suitable donor-acceptor pair for light-harvesting materials which was in agreement with their good antibacterial activity.

  DOI：

  10.1080/00397911.2020.1788601

文献信息

• Design, Synthesis and Photostability of Novel 1,8-naphthalimide PAMAM Light-harvesting Dendrons
  作者：Nikolai I. Georgiev、Vladimir B. Bojinov

  DOI：10.1007/s10895-010-0689-y

  日期：2011.1

  This paper reports on the divergent synthesis, photophysical properties and photodegradation of novel PAMAM dendrons, core and peripherally functionalized with 1,8-naphthalimide fluorophores. The novel compounds were configured as light-harvesting antennae where the system surface is labeled with blue emitting 4-allyloxy-1,8-naphthalimide “donor” fluorophores capable of absorbing light and efficiently transferring the energy to a single yellow-green emitting 4-alkylamino-1,8-naphthalimide “acceptor” dye. The focal 1,8-naphthalimide fluorophores in the antennae were modified with a HALS fragment (2,2,6,6-tetramethylpiperidine or 1,2,2,6,6-pentamethylpiperidine) with a view to improve their photostability. Novel light-harvesting systems showed highly efficient energy transfer, depending on the volume of the core substituent. Due to the HALS fragments the chromophoric system of the novel antennae showed higher photostability, while the photostability of the PAMAM scaffold was found to be lower.

  本文报告了新型 PAMAM 树枝状化合物的不同合成、光物理性质和光降解情况，这些树枝状化合物的核心和外围均由 1,8-萘二甲酰亚胺荧光团功能化。这些新型化合物被配置为光收集天线，系统表面标记有蓝色发光的 4-烯丙氧基-1,8-萘二甲酰亚胺 "供体 "荧光团，它们能够吸收光并将能量有效地传递给单个黄绿色发光的 4-烷基氨基-1,8-萘二甲酰亚胺 "受体 "染料。用 HALS 片段（2,2,6,6-四甲基哌啶或 1,2,2,6,6-五甲基哌啶）修饰了触角中的焦点 1,8-萘二甲酰亚胺荧光团，以提高它们的光稳定性。新颖的光收集系统显示出高效的能量转移，这取决于核心取代基的体积。由于 HALS 片段的存在，新型天线的色度系统具有更高的光稳定性，而 PAMAM 支架的光稳定性较低。
• US5202318A
  申请人：——

  公开号：US5202318A

  公开（公告）日：1993-04-13
• [EN] NOVEL AZABICYCLOBENZISOQUINOLINES
  申请人：SYNTEX (U.S.A.) INC.

  公开号：WO1992021673A1

  公开（公告）日：1992-12-10

  (EN) Compounds of formula (I) in which p is 0 or 1; Z is C=O; X and Y are independently selected from hydrogen, halogen, hydroxy, lower alkoxy, benzyloxy, lower alkyl, nitro, amino, aminocarbonyl, (lower alkyl)amino, di(lower alkyl)amino; each R1 is independently selected from hydrogen, hydroxy, alkyl and alkoxy; each R2 is independently hydrogen or alkyl; and R3 is hydrogen, lower alkyl, lower alkenyl or a group R4-C1-3 alkyl in which R4 is phenyl or phenoxy optionally substituted by one halogen substituent; and the pharmaceutically acceptable salts, individual isomers, mixtures of isomers, are 5HT interactors. Processes for preparation, compositions, and methods of use thereof are disclosed.(FR) Composés de la formule (I), dans laquelle p représente 0 ou 1; Z représente C=O; X et Y sont sélectionnés indépendamment parmi hydrogène, halogène, hydroxy, alcoxy inférieur, benzyloxy, alkyle inférieur, nitro, amino, aminocarbonyle, amino(alkyle inférieur), diamino(alkyle inférieur); chaque R1 est sélectionné indépendamment parmi hydrogène, hydroxy, alkyle et alcoxy; chaque R2 représente indépendamment hydrogène ou alkyle; et R3 représente hydrogène, alkyle inférieur, alcényle inférieur ou un groupe R4-alkyle C1-3 dans lequel R4 représente phéhyle ou phénoxy facultativement substitué par un substituant halogène; et les sels pharmaceutiquement utilisables, des isomères individuels ainsi que des mélanges d'isomères constituent des agents d'interaction 5HT. L'invention concerne également des procédés de préparation, des compositions et leurs procédés d'utilisation.
• Tricyclic compounds acting at serotonin receptor subtypes
  申请人：Syntex (U.S.A.) Inc.

  公开号：US05202318A1

  公开（公告）日：1993-04-13

  Compounds of Formula I: ##STR1## in which Z is CH.sub.2 or C.dbd.O; X and Y are independently selected from hydrogen, halogen, hydroxy, lower alkoxy, lower alkyl, nitro, amino, aminocarbonyl, (lower alkyl)amino, di(lower alkyl)amino and (lower alkanoyl)amino; and R.sup.1 is a group selected from Formulae (a), (b), (c) (d) and (e): ##STR2## in which p is 0 or 1; n is 1, 2 or 3; R.sup.2 is hydrogen, lower alkyl, C.sub.3-8 cycloalkyl, C.sub.3-8 cycloalkyl-C.sub.12 alkyl, or a group R.sup.6 -C.sub.1-2 alkyl in which R.sup.6 is thienyl, pyrrolyl or furyl optionally substituted by one or two substituents selected from lower alkyl, lower alkoxy, trifluoromethyl or halogen, or is phenyl optionally substituted by one or two substituents selected from C.sub.1-4 alkoxy, trifluoromethyl, halogen, nitro, carboxy, esterified carboxy, and C.sub.1-4 alkyl optionally further substituted by hydroxy, C.sub.1-4 alkoxy, carboxy, esterified carboxy or in vivo hydrolyzable acyloxy; each R.sup.3 is independently selected from hydrogen, hydroxy, alkyl and alkoxy; each R.sup.4 is independently hydrogen or alkyl; and R.sup.5 is hydrogen, lower alkyl, C.sub.3-8 cycloalkyl, C.sub.3-8 cycloalkyl-C.sub.1-2 alkyl, alkenyl, alkynyl or a group R.sup.7 -C.sub.1-3 alkyl in which R.sup.7 is phenyl or phenoxy optionally substituted by one or two substituents selected from C.sub.1-4 alkoxy, trifluoromethyl, halogen, nitro, carboxy, esterified carboxy, and C.sub.1-4 alkyl optionally further substituted by hydroxy, C.sub.1-4 alkoxy, carboxy, esterified carboxy or in vivo hydrolyzable acyloxy; and the pharmaceutically acceptable salts, individual isomers, mixtures of isomers, processes for preparation, compositions, and methods of use thereof.

  化合物的化学式I：##STR1## 其中Z为CH.sub.2或C.dbd.O；X和Y分别选自氢、卤素、羟基、低烷氧基、低烷基、硝基、氨基、氨基甲酰、(低烷基)氨基、二(低烷基)氨基和(低脂肪酰)氨基；R.sup.1为从式(a)、(b)、(c)、(d)和(e)中选择的基团：##STR2## 其中p为0或1；n为1、2或3；R.sup.2为氢、低烷基、C.sub.3-8环烷基、C.sub.3-8环烷基-C.sub.12烷基，或R.sup.6-C.sub.1-2烷基，其中R.sup.6为噻吩基、吡咯基或呋喃基，可选择地被一个或两个选自低烷基、低烷氧基、三氟甲基或卤素的取代基取代，或者为苯基，可选择地被一个或两个选自C.sub.1-4烷氧基、三氟甲基、卤素、硝基、羧基、酯化羧基和C.sub.1-4烷基的取代基取代，可选择地进一步被羟基、C.sub.1-4烷氧基、羧基、酯化羧基或体内可水解的酰氧基取代；每个R.sup.3独立地选自氢、羟基、烷基和烷氧基；每个R.sup.4独立地选自氢或烷基；R.sup.5为氢、低烷基、C.sub.3-8环烷基、C.sub.3-8环烷基-C.sub.1-2烷基、烯基、炔基或R.sup.7-C.sub.1-3烷基，其中R.sup.7为苯基或苯氧基，可选择地被一个或两个选自C.sub.1-4烷氧基、三氟甲基、卤素、硝基、羧基、酯化羧基和C.sub.1-4烷基的取代基取代，可选择地进一步被羟基、C.sub.1-4烷氧基、羧基、酯化羧基或体内可水解的酰氧基取代；以及其药学上可接受的盐、单体异构体、异构体混合物、制备方法、组合物和使用方法。
• Design, photochemistry and antibacterial evaluation of novel light-harvesting antenna
  作者：Alaa R. Sakr、Nikolai I. Georgiev、Vladimir B. Bojinov

  DOI：10.1080/00397911.2020.1788601

  日期：2020.10.1

  Novel light-harvesting compound6,based on 1,8-naphthalimide donors and perylenediimide acceptor were synthesized. The light-harvesting compound6showed intensive absorption band in range between 390 and 560 nm, that is 50 nm wider in comparison with the absorption of the model perylene dye. The novel antenna6has a higher ability to collect photons from environment in comparison with the single perylene diimide dyes. The chosen fluorophore units are suitable donor-acceptor pair for light-harvesting materials which was in agreement with their good antibacterial activity.