3027-38-1

Usage

Uses

Used in Diagnostics:
3-Nitro-1,8-naphthalic anhydride is used as a reagent for the synthesis of monoboronic acid fluorescent sensors. These sensors exhibit emission suitable for ratiometric testing and display sensitivity for glucose relative to fructose and galactose, making them valuable tools in the detection and monitoring of blood sugar levels in medical diagnostics.
Used in Pharmaceutical Industry:
3-Nitro-1,8-naphthalic anhydride is used as a starting reagent in the synthesis of 5-substituted naphthalimide derivatives. These derivatives have been found to exhibit high anti-cancer activity, making them promising candidates for the development of new cancer treatments. The use of 3-Nitro-1,8-naphthalic anhydride in this context contributes to the advancement of cancer research and the development of more effective therapies for patients.

InChI:InChI=1/C12H5NO5/c14-11-8-3-1-2-6-4-7(13(16)17)5-9(10(6)8)12(15)18-11/h1-5H

Upstream product

• 81-84-5 1,8-Naphthalic anhydride 
• 83-32-9 acenaphthene 

Downstream Products

• 26491-50-9 5-nitro-2-phenyl-1H-benzo[de]isoquinoline-1,3(2H)-dione 
• 66266-36-2 5-nitro-1H-benz[de]isoquinoline-1,3(2H)-dione 
• 54824-20-3 pinafide 
• 54824-19-0 5-Nitro-2-(2-piperidin-1-yl-ethyl)-benzo[de]isoquinoline-1,3-dione 
• 96807-70-4 5-Nitro-2-(2-piperazin-1-yl-ethyl)-benzo[de]isoquinoline-1,3-dione 
• 4507-84-0 3-nitro-1-naphthoic acid 
• 91901-44-9 ethyl 6-nitro-1-naphthoate 
• 79070-65-8 2-(2-hydroxyethyl)-5-nitro-1H-benzo[de]isoquinoline-1,3(2H)-dione 
• 54824-17-8 mitonafide 
• 69408-73-7 2-(3-Dimethylamino-propyl)-5-nitro-benzo[de]isoquinoline-1,3-dione 
• 54824-18-9 5-nitro-2-(2-diethylaminoethyl)-1H-benzisoquinoline-1,3(2H)-dione 
• 79070-62-5 2-(2-methylaminoethyl)-5-nitrobenzisoquinoline-1,3-dione 
• 95092-65-2 phenyl 3-nitro-1-naphthoate 
• 95092-67-4 phenyl 6-nitro-1-naphthoate 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of 3-nitro-1,8-naphthalimides as potential antitumor agents

A series of 3-nitro-naphthalimides 1(1a–1h) were designed and synthesized as antitumor agents. MTT assay results showed that all these compounds exhibited obvious antiproliferative activity against SKOV3, HepG2, A549, T-24 and SMMC-7721 cancer cell lines, while compound 1a displayed the best antiproliferative activity against HepG2 and T-24 cell lines in comparison with mitonafide, with IC50 of 9.2 ± 1.8 and 4.133 ± 0.9 μM, respectively. In vivo antiproliferative activity assay results showed that compound 1a exhibited good antiproliferative activity in the HepG2 and T-24 models, compared with mitonafide. Action mechanism results showed that compound 1a could induced the damage of DNA and the inhibition topo I, accompanying by inducing the G2-stage arresting and the apoptosis of T-24 cancer cells through up-regulating expression levels of cyclin B1, cdc 2-pTy, Wee1, γH2AX, p21, Bax and cytochrome c and down-regulating expression of Bcl-2.

3-Nitro-naphthalimide and nitrogen mustard conjugate NNM-25 induces hepatocellular carcinoma apoptosis via PARP-1/p53 pathway

Hepatocellular carcinoma (HCC) is one of the main causes of death in cancer. Some naphthalimide derivatives exert high anti-proliferative effects on HCC. In this study, it is confirmed that 3-nitro-naphthalimide and nitrogen mustard conjugate (NNM-25), a novel compound conjugated by NNM-25, displayed more potent therapeutic action on HCC, both in vivo and in vitro, than amonafide, a naphthalimide drug in clinical trials. More importantly, preliminary toxicological evaluation also supported that NNM-25 exhibited less systemic toxicity than amonafide at the therapeutic dose. The antitumor mechanism of conjugates of naphthalimides with nitrogen mustard remains poorly understood up to now. Here, we first reported that apoptosis might be the terminal fate of cancer cells treated with NNM-25. Inhibition of p53 by siRNA resulted in a significant decrease of NNM-25-induced apoptosis, which corroborated that p53 played a vital role in the cell apoptosis triggered by NNM-25. NNM-25 inhibited the PARP-1 activity, AKT phosphorylation, up-regulated the protein expression of p53, Bad, and mTOR as well as down-regulating the protein expression of Bcl-2 and decreasing mitochondrial membrane potential. It also facilitated cytochrome c release from mitochondria to cytoplasm, activated caspase 8, caspase 9, and caspase 3 in HepG2 cells in vitro, as also authenticated in H22 tumor-bearing mice in vivo. Collectively, the conjugation of naphthalimides with nitrogen mustard provides favorable biological activity and thus is a valuable strategy for future drug design in HCC therapy.

An endoplasmic reticulum targetable turn-on fluorescence probe for imaging application of carbon monoxide in living cells

Carbon monoxide (CO) is a significant mediator in regulating endoplasmic reticulum (ER) stress, and its level may play a potential role in the treatment of vascular diseases combined with ER stress. In-situ visualization of CO in the ER helps to elucidate

Naphthalimide-polyamine conjugate as well as preparation method and application thereof

The invention discloses a naphthalimide-polyamine conjugate, which has a structural general formula as shown in I, a novel skeleton, high efficiency, low toxicity and good inhibitory activity for tumor cells. The invention also discloses a preparation method of the conjugate. Firstly, 3-amino groups with toxic and side effects of amonafide are removed, a phenylpyrazole structure fragment is introduced to the naphthalimide parent naphthalene ring, and a naphthalimide side chain with a polyamine chain is modified, acetyltransferase in vivo is prevented from acetylating the amino groups on the naphthalene ring of amonafideand, and toxic and side effects are reduced; and further by introducing a low-toxicity phenyl pyrazole active structure fragment, the naphthalimide polyamine conjugate witha novel skeleton, high efficiency and low toxicity is synthesized; and secondly, quinazoline with low toxicity is introduced to replace hydrogen atoms of amonafide 3-amino, so that the naphthalimide polyamine conjugate with anti-tumor activity and low toxicity is obtained. The invention also discloses an application of the conjugate in preparation of antitumor drugs, and good development potentialis realized.

A naphthalimide-polyamine conjugate preferentially accumulates in hepatic carcinoma metastases as a lysosome-targeted antimetastatic agent

Disseminated tumors lead to approximately 90% of cancer-associated deaths especially for hepatocellular carcinoma (HCC), indicating the imperative need of antimetastatic drugs and the ineffectiveness of current therapies. Recently polyamine derivatives have been identified as a promising prospect in dealing with metastatic tumors. Herein, a novel class of naphthalimide-polyamine conjugates 8a-8d, 13a-13c, 17 and 21 were synthesized and the mechanism was further determined. The polyamine conjugate 13b displayed remarkably elevated anti-tumor and anti-metastatic effects (76.01% and 75.02%) than the positive control amonafide (46.91% and 55.77%) at 5 mg/kg in vivo. The underlying molecular mechanism indicated that in addition to induce DNA damage by up-regulating p53 and γH2AX, 13b also targeted lysosome to modulate polyamine metabolism and function in a totally different way from that of amonafide. Furthermore, the HMGB1/p62/LC3II/LC3I and p53/SSAT/β-catenin pathways were mainly involved in the inhibition of 13b-induced HCC metastasis by targeting polyamine transporters (PTs) overexpressed in HCC. At last, 13b down-regulated the concentrations of Put, Spd and Spm by modulating polyamine metabolism key enzymes SSAT and PAO, which favored the suppression of fast growing tumor cells. Taken together, our study implies a promising strategy for naphthalimide conjugates to treat terminal cancer of HCC by targeting autophagy and tumor microenvironment with reduced toxicities and notable activities.

Naphthalimide indole heterocyclic compound as well as preparation method and application thereof

The invention belongs to the technical field of medicinal chemistry, and particularly relates to a naphthalimide indole heterocyclic compound as well as a preparation method and application thereof. The naphthalimide indole heterocyclic compound has good anti-tumor activity, the in-vivo and in-vitro anti-tumor activity of the naphthalimide indole heterocyclic compound is better than that of dinafide, and the anti-tumor spectrum of the naphthalimide indole heterocyclic compound is wide. Different from classical dinafide, the compound regulates and controls subcellular organelle and cell nucleus functions to reverse drug resistance by targeting the contents of key enzyme PAO (polyamine oxidase) and three endogenous small molecules Put (putrescine), Spd (spermidine) and Spm (spermine) in a tumor polyamine microenvironment, and enhances anti-tumor immune response at the same time; and the compound has good treatment potential on advanced metastatic tumors. The complex provided by the invention also solves the problems of poor solubility, complicated clinical compatibility, poor patient immunity in clinical application of chemotherapeutic drugs and the like of naphthalimide analogues represented by dinafide in the prior art, and has good water solubility.

Fluorescent probe for detecting tiredness level Preparation method and application thereof

The invention discloses a fluorescence probe for detecting the level of hypoxia, a preparation method and application thereof, and can realize specific response Na. 2 S2 O4 The fluorescence probe is used for detecting the tiredness level, and the structure is as follows. The probe comprises a nitrogen-nitrogen double bond, which can be broken down in a hypoxic environment to cause fluorescence recovery of the compound. The naphthalimide is introduced as a fluorophore, and has the characteristics of stable fluorescence and high fluorescence quantum efficiency. The fluorescent probe is simple and convenient to prepare, obvious in spectral change, good in specificity effect, small in cytotoxicity, good in imaging effect and good in specificity detection Na. 2 S2 O4 , The fluorophore precursor and the anti-tumor drug nitrogen mustard compound can be released under the hypoxic condition, the tumor cell growth can be inhibited while the hypoxia imaging is carried out, the diagnosis and treatment integrated function is achieved, and the application prospect is good.

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.

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.

Preparation method of 1,8-disubstituted naphthalene series polycyclic aromatic hydrocarbon mononitration derivative

The invention provides a preparation method of 1,8-disubstituted naphthalene series polycyclic aromatic hydrocarbon mononitration derivative. The preparation method is characterized by comprising thefollowing steps: S1, dissolving 1,8-disubstituted naphthalene series polycyclic aromatic hydrocarbon and subgroup metal nitrate in an organic solvent, performing a nitration reaction under 10-60 DEG Cfor 4-10 h, and then monitoring by TLC (Thin layer chromatography) till a raw material point disappears to finish the reaction; S2, cooling a product obtained in S1 to room temperature, performing suction filtration, washing filter cake with 5-10 mL of H2O and anhydrous C2H5OH separately, and performing vacuum drying to obtain the 1,8-disubstituted naphthalene series polycyclic aromatic hydrocarbon mononitration derivative. According to the preparation method of the 1,8-disubstituted naphthalene series polycyclic aromatic hydrocarbon mononitration derivative, the product yield is 93%-96%; theproduct purity is 98%-99.5%; compared with the prior art, the preparation method has the characteristics of high product yield, high purity, low cost and simple process, and is easy to industrialize.