4-(N-(1,8-萘酰亚胺))-N-丁酸 | 88909-96-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 中文名称: 4-(N-(1,8-萘酰亚胺))-N-丁酸
• 英文名称: virstatin
• 英文别名: 4-(1,3-dioxo-1H-benzo [de]isoquinolin-2(3H)-yl)butanoic acid；4-(1,3-dioxobenzo[de]isoquinolin-2-yl)butanoic acid
• CAS: 88909-96-0
• 化学式: C₁₆H₁₃NO₄
• mdl: MFCD00181400
• 分子量: 283.284
• InChiKey: ZHXRDXTYPCPBTI-UHFFFAOYSA-N

物化性质

• 熔点：
  186-188 °C(Solv: ethanol (64-17-5))
• 沸点：
  536.5±33.0 °C(Predicted)
• 密度：
  1.403±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：33mg/mL； DMSO：33mg/mL； DMSO:PBS(pH 7.2) (1:3): 0.25 mg/mL
• 碰撞截面：
  156.5 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.187
• 拓扑面积：
  74.7
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090
• 储存条件：
  -20°C，密闭保存，干燥环境

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-(1,3-Dioxo-1h,3h-benzo[de]isoquinolin-2-yl)-butyric acid
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 4-(1,3-Dioxo-1h,3h-benzo[de]isoquinolin-2-yl)-butyric acid
CAS number: 88909-96-0

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C16H13NO4
Molecular weight: 283.3

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

Virstatin 抑制菌毛系统的合成，并阻止铜绿假单胞菌(A. baumannii)生物膜的形成。此外，它还抑制转录激活剂ToxT的二聚化。

反应信息

• 作为反应物：
  描述：

  4-(N-(1,8-萘酰亚胺))-N-丁酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 4-(1,3-dioxobenzo[de]isoquinolin-2-yl)butanoyl chloride
  参考文献：
  名称：

  多发色羰基桥联三芳基胺的合成及其光物理性质

  摘要：

  介绍了两种新型多发色化合物的合成和光物理性质。他们的分子设计包括羰基桥联的三芳基胺核和萘二甲酰亚胺或4-（5-己基-2,2'-联噻吩）萘二甲酰亚胺作为周边的第二个生色团。侧生色团通过酰胺键和短烷基间隔基连接到核上。合成方法证明了羰基桥联的三芳基胺的直接官能化策略。这些化合物与三种参考化合物的稳态和时间分辨光谱研究为两种多发色化合物的能量转移提供了清晰的证据。能量转移的方向取决于所用的侧向生色团。此外，

  DOI：

  10.1002/chem.201403667
• 作为产物：
  描述：

  萘亚胺 在 盐酸 、 四丁基碘化铵 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 4-(N-(1,8-萘酰亚胺))-N-丁酸
  参考文献：
  名称：

  设计，合成和生物学评估与三环DNA嵌入剂连接的新的寡吡咯羧酰胺作为潜在的DNA配体或拓扑异构酶抑制剂。

  摘要：

  在小沟结合和嵌入DNA配体的设计和合成过程中，合成了一些新的寡吡咯羧酰胺。这些杂合分子（combilexins）在N末端具有可变的和构象柔性的间隔基。作为插入的三环系统，cri啶酮，a啶，蒽醌以及在特殊情况下的亚氨基二苯乙烯终止了吡咯链的N末端。通过NCI抗肿瘤筛选检查了细胞毒性，此外，还进行了生物物理和生化研究，以便获得有关该新系列分子的DNA结合特性和拓扑异构酶抑制作用的一些信息。

  DOI：

  10.1016/j.ejmech.2006.12.039

文献信息

• Naphthalimide Platinum(IV) Compounds as Antitumor Agents with Dual DNA Damage Mechanism to Overcome Cisplatin Resistance
  作者：Qingpeng Wang、Guoshuai Li、Zhifang Liu、Xiaoxiao Tan、Zhuang Ding、Jing Ma、Lanjie Li、Dacheng Li、Jun Han、Bingquan Wang

  DOI：10.1002/ejic.201800799

  日期：2018.11

  potential in overcoming the drug resistance of cisplatin. Furthermore, naphthalimide platinum(IV) complexes could effectively combine with HSA by electrostatic force, which would influence the drug distribution and bioactivities in vivo. Moreover, the accumulation of the tested platinum(IV) compounds in whole cells and DNA is remarkably enhanced in comparison with cisplatin and oxaliplatin.

  设计，合成并评估了具有双重DNA损伤机理的新系列萘二甲酰亚胺铂（IV）化合物的抗肿瘤活性。铂（IV）化合物可与DNA结合并通过萘二甲酰亚胺片段造成DNA损伤。然后，在还原性微环境中释放的铂（II）配合物将引起显着的继发性DNA损伤。一些标题化合物表现出良好的抗肿瘤活性，并且在克服顺铂的耐药性方面具有巨大潜力。此外，萘二甲酰亚胺铂（IV）配合物可以通过静电力与HSA有效结合，从而影响体内的药物分布和生物活性。此外，与顺铂和奥沙利铂相比，受试铂（IV）化合物在整个细胞和DNA中的积累显着增强。
• 萘酰亚胺四价铂类化合物、制备方法及其在制 备抗肿瘤药物中的应用
  申请人：聊城大学

  公开号：CN108358973B

  公开（公告）日：2020-08-21

  本发明将萘酰亚胺分子引入四价铂母核，设计合成了一系列新型萘酰亚胺修饰四价铂类化合物，考察了其抗癌、抗肿瘤能力；这一系列原始创新性研究，有望获得多种对肿瘤有效的先导分子，为解决传统二价铂类药物存在的缺陷提供新候选药物分子，也为四价铂类化合物的修饰开辟新的途径；此类源头上创新药物研究，对国民经济和社会发展及人民健康等都将具有重要的理论价值和实际意义。
• Cystine-derived bis-naphthalimides as stimuli-responsive fluorescent gelators
  作者：Rupam J. Sarma、Kakali Devi

  DOI：10.1039/c4nj01755b

  日期：——

  Stimuli-responsive fluorescence modulation of two cystine-derived bis-naphthalimide gelators was demonstrated using fluoride/tetrafluoroborate anions as the chemical inputs.

  使用氟化物/四氟硼酸盐作为化学输入，展示了两种半胱氨酸衍生的双萘亚胺凝胶剂的刺激响应荧光调制。
• Target Enzyme‐Activated Two‐Photon Fluorescent Probes: A Case Study of CYP3A4 Using a Two‐Dimensional Design Strategy
  作者：Jing Ning、Wei Wang、Guangbo Ge、Peng Chu、Feida Long、Yongliang Yang、Yulin Peng、Lei Feng、Xiaochi Ma、Tony D. James

  DOI：10.1002/anie.201903683

  日期：2019.7.15

  development of fluorescent probes for monitoring target enzymes is still a great challenge owing to the lack of efficient ways to optimize a specific fluorophore. Herein, a practical two‐dimensional strategy was designed for the development of an isoform‐specific probe for CYP3A4, a key cytochrome P450 isoform responsible for the oxidation of most clinical drugs. In first dimension of the design strategy

  由于缺乏优化特定荧光团的有效方法，用于监测目标酶的荧光探针的快速开发仍然是一个巨大的挑战。本文设计了一种实用的二维策略，用于开发针对CYP3A4的同工型特异性探针，CYP3A4是负责大多数临床药物氧化的关键细胞色素P450同工型。在设计策略的第一个维度中，使用基于集合的虚拟筛选有效地选择了CYP3A4的潜在双光子荧光底物（NN）。在第二维中，将各种取代基引入到NN中，以优化异构体的选择性和反应性。最后，具有理想的选择性和灵敏度，NEN已成功应用于活细胞和斑马鱼中CYP3A4的实时检测。这些发现表明我们的策略对于开发针对靶酶的同工型特异性探针是可行的。
• Design and synthesis of a new series of low toxic naphthalimide platinum(IV) antitumor complexes with dual DNA damage mechanism
  作者：Qingpeng Wang、Xiaoxiao Tan、Zhifang Liu、Guoshuai Li、Ruiyan Zhang、Jinjian Wei、Shiben Wang、Dacheng Li、Bingquan Wang、Jun Han

  DOI：10.1016/j.ejps.2018.08.032

  日期：2018.11

  Naphthalimide platinum(IV) antitumor complexes with potential dual DNA damage mechanism were designed, synthesized and evaluated for antitumor activities. The incorporation of DNA targeted naphthalimide group to the platinum(IV) system exerts much positive impacts on their antitumor efficacy. The mechanism research reveals that the title compounds could interact with dsDNA in platinum(IV) form via the

  设计，合成和评估了具有潜在双重DNA损伤机制的萘二甲酰亚胺铂（IV）抗肿瘤复合物。DNA靶向的萘二甲酰亚胺基团结合到铂（IV）系统中对其抗肿瘤功效产生了很多积极的影响。机理研究表明，标题化合物可通过萘二甲酰亚胺基团与铂（IV）形式的dsDNA相互作用，并引起DNA损伤。进一步还原将释放出铂（II）配合物和萘二甲酰亚胺酸，这将对DNA造成明显的二次破坏。此外，萘二甲酰亚胺铂（IV）化合物可通过静电力与人血清白蛋白结合，有利于它们在血液中的储存和运输。此外，标题化合物在肿瘤细胞中表现出更高的积累，