307299-14-5

Basic information

• Product Name: 3-(6-nitro-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)propanoic acid
• Synonyms: 3-(6-nitro-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)propanoic acid
• CAS NO: 307299-14-5
• Molecular Formula: C₁₅H₁₀N₂O₆
• Molecular Weight: 314.2497
• Mol File: 307299-14-5.mol

Chemical Properties

• Melting Point: 198-200 °C(Solv: ethanol (64-17-5))
• Boiling Point: 607.2±45.0 °C(Predicted)
• Appearance: /
• Density: 1.593±0.06 g/cm3(Predicted)
• PKA: 4.22±0.10(Predicted)
• CAS DataBase Reference: 3-(6-nitro-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)propanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(6-nitro-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)propanoic acid(307299-14-5)
• EPA Substance Registry System: 3-(6-nitro-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)propanoic acid(307299-14-5)

Safety Data

• Hazardous Substances Data: 307299-14-5(Hazardous Substances Data)

Upstream product

• 34087-02-0 2-nitro-1,8-naphthalic anhydride 
• 107-95-9 3-amino propanoic acid 
• 83-32-9 acenaphthene 
• 81-84-5 1,8-Naphthalic anhydride 
• 6642-29-1 4-nitronaphthalic-1,8-anhydride 

Downstream Products

• 1401539-55-6 C₄₅H₄₈N₄O₇PS₂⁽¹⁺⁾ 
• 1401539-54-5 C₃₅H₃₁N₃O₃P⁽¹⁺⁾ 
• 1401539-53-4 C₄₀H₃₉N₃O₆PS₂⁽¹⁺⁾ 

Relevant articles and documents

The synthesis and fluorescence of novel N-substituted-1,8-naphthylimides

(Chemical Equation Presented) The synthesis and characterisation of a series of novel 4-acylamino and 4-alkylamino-N-1,8-naphthalimides is described. The UV-visible absorption and emission properties of the compounds are reported. Significant solvent effects are noted for 4-n-butyl-9-n-butyl-1,8- naphthylimide. The incorporation of acetyl and chloroacetyl groups into the 4-substituent markedly increases the fluorescence quantum yield compared with 4-alkylamino substituemnts.

Synthesis, photophysical characterisation and antimicrobial activity of a new anionic PAMAM dendrimer

A new anionic dendrimer (D1) has been synthesized and characterized by modification of a poly(amidoamine) (PAMAM) dendrimer with 3-(6-nitro-1,3-dioxo-1H-benzo[de]isoquinolin-2(3 H)-yl)propanoic acid (NI1). Its photophysical characteristics have been investigated in organic solvents of different polarity and a positive solvatochromism has been observed. The effect of the pH medium on the fluorescence intensity has been investigated and it has been shown that in the highly alkaline medium the dendrimer emits intense fluorescence. The dendrimer and its monomeric structural analogue have been loaded on a cotton fabric and the release of substances from the surface of the cotton fabric has been investigated. The compounds have been screened for antimicrobial and cytotoxic activities. They have been found more active against Gram-positive bacteria. The dendrimer exhibits slightly lower activity than the monomeric analogue, but is found to be significantly less cytotoxic. The deposited on cotton fabric D1 prevents the formation of bacterial biofilm on the fabric surface.

Tetravalent platinum naphthalimide complex, preparation method and application thereof

The invention belongs to the technical field of medicinal chemistry, and particularly relates to a tetravalent platinum naphthalimide complex, a preparation method and application thereof. The tetravalent platinum naphthalimide complex has good anti-tumor activity, which is better than that of cis-platinum and oxaliplatin, and the tetravalent platinum naphthalimide complex has better stability than bivalent platinum like cis-platinum, carboplatin and oxaliplatin. According to the invention, the naphthalimide modified tetravalent platinum has good targeting performance on tumor cells, high selectivity on tumor cells is improved, and different from a classic divalent platinum drug, the complex provided by the invention regulates and controls subcellular organelles and cell nucleus functionsto reverse drug resistance by targeting a tumor high polyamine microenvironment, and relieves immunosuppression of T cells around tumors at the same time. The complex provided by the invention also solves the problems of poor solubility, tedious clinical compatibility, poor patient immunity in clinical application of chemotherapeutic drugs and the like of previous bivalent platinum antitumor drugs, and has good fat solubility and water solubility.

A Pt(IV)-based mononitro-naphthalimide conjugate with minimized side-effects targeting DNA damage response via a dual-DNA-damage approach to overcome cisplatin resistance

Platinum(Pt)(II) drugs and new Pt(IV) agents behave the dysregulation of apoptosis as the result of DNA damage repair and thus, are less effective in the treatment of resistant tumors. Herein, mononitro-naphthalimide Pt(IV) complex 10b with minimized side-effects was reported targeting DNA damage response via a dual-DNA-damage approach to overcome cisplatin resistance. 10b displayed remarkably evaluated antitumor (70.10percent) activities in vivo compared to that of cisplatin (52.88percent). The highest fold increase (FI) (5.08) for A549cisR cells and the lowest (0.72) for A549 indicated 10b preferentially accumulated in resistant cell lines. The possible molecular mechanism indicates that 10b targets resistant cells in a totally different way from the existing Pt drugs. The cell accumulation and the Pt levels in genomic DNA from 10b is almost 5 folds higher than that of cisplatin and oxaliplatin, indicating the naphthalimide moiety in 10b exhibits preferentially DNA damage. Using 5′-dGMP as a DNA model, the DNA-binding properties of 10b (1 mM) with 5′-dGMP (3 mM) in the presence of ascorbic acid (5 mM) deduced that 10b was generated by the combination of cisplatin with 5′-dGMP after reduction by ascorbic acid. Moreover, 10b promoted the expression of p53 gene and protein more effectively than cisplatin, leading to the increased anticancer activity. The up-regulated γH2A.X and down-regulated RAD51 indicates that 10b not only induced severe DNA damage but also inhibited the DNA damage repair, thus resulting in its higher cytotoxicity in comparison to that of cisplatin. Their preferential accumulation in cancer cells (SMMC-7721) compared to the matched normal cells (HL-7702 cells) demonstrated that they were potentially safe for clinical therapeutic use. In addition, the higher therapeutic indices of 10b for 4T1 cells in vivo indicated that naphthalimide-Pt(IV) conjugates behaved a vital function in the treatment of breast cancer. For the first time, our study implies a significant strategy for Pt drugs to treat resistance cancer targeting DNA damage repair via dual DNA damage mechanism in a totally new field.

NITROGEN-BASED HOMO-CAMPTOTHECIN DERIVATIVES

(20) esters of camptothecin analogs are provided. The compounds are (20) esters of an aminoalkanoic acid or an imidoalkanoic acid and homocamptothecin, which is optionally substituted at the 7, 9, 10, 11, and 12 positions of the homocamptothecin ring. The

Method of inhibiting neurotrophin-receptor binding

The present invention relates to compositions which inhibit the binding of nerve growth factor to the p75NTRcommon neurotrophin receptor and methods of use thereof. In one embodiment, the compound which inhibits binding of nerve growth factor to p75NTRcomprises, particularly when bound to nerve growth factor, at least two of the following: (1) a first electronegative atom or functional group positioned to interact with Lys34of nerve growth factor; (2) a second electronegative atom or functional group positioned to interact with Lys95of nerve growth factor; (3) a third electronegative atom or functional group positioned to interact with Lys88of nerve growth factor; (4) a fourth electronegative atom or functional group positioned to interact with Lys32of nerve growth factor; and (5) a hydrophobic moiety which interacts with the hydrophobic region formed by Ile31, Phe101and Phe86of nerve growth factor.