4497-69-2

Usage

Molecular weight

303.74 g/mol

Chemical group

Naphthalene derivatives

Organic compound

Yes

Benzylamino group attached

Yes

Chlorine atom position

3-position of the naphthalene ring

Used in organic synthesis

Yes

Applications

Pharmaceutical and chemical industries

Value for research and development

High

Upstream product

• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 
• 100-46-9 benzylamine 

Downstream Products

• 4613-08-5 N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-N-benzylacetamide 
• 24055-56-9 3-diazonaphthalene-1,2,4(3H)-trione 
• 100-52-7 benzaldehyde 

Relevant academic research and scientific papers

A simple synthesis of 3,4-dihydrobenzo[f]quinoxalin-6(2H)-one derivatives substituted in the ring B

[Figure not available: see fulltext.] We followed a simple, inexpensive, and efficient route to synthesize a series of 3,4-dihydrobenzo[f]quinoxalin-6(2H)-one derivatives substituted in the ring B, with the expectation that this scaffold might exhibit antineoplastic activity. 5-Chlorobenzo[f]quinoxalin-6-ylacetate and 4-benzylbenzo[f]quinoxalin-6(4H)-one were obtained for the first time.

Composition for Distructing Microalgae

The present invention relates to a composition for destroying microalgae, more specifically, to a composition for destroying microalgae containing naphthoquinone compounds having a specific exchange group. The composition for destroying microalgae, according to the present invention, can prevent green tide and red tide by being processed in areas such as cultivation facilities for microalgae, areas in which the green tide or the red tide occur, or areas expected to occur the green tide or the red tide.

Dichloro-naphthoquinone as a non-classical inhibitor of the mycobacterial carbonic anhydrase Rv3588c

The soluble mycobacterial carbonic anhydrases Rv3588c and Rv1284 belong to a different class of carbonic anhydrases than those found in humans, making them attractive drug targets by using the inherent differences in the folds of the different classes. By screening a natural product library, we identified naphthoquinone derivatives as a novel non-classical inhibitor scaffold of mycobacterial carbonic anhydrases that lack the sulfonamide/sulfamate group and thus did not affect human carbonic anhydrase II.

Dioxonaphthoimidazoliums are Potent and Selective Rogue Stem Cell Clearing Agents with SOX2-Suppressing Properties

Pluripotent stem cells are uniquely positioned for regenerative medicine, but their clinical potential can only be realized if their tumorigenic tendencies are decoupled from their pluripotent properties. Deploying small molecules to remove remnant undifferentiated pluripotent cells, which would otherwise transform into teratomas and teratomacarcinomas, offers several advantages over non-pharmacological methods. Dioxonapthoimidazolium YM155, a survivin suppressant, induced selective and potent cell death of undifferentiated stem cells. Herein, the structural requirements for stemotoxicity were investigated and found to be closely aligned with those essential for cytotoxicity in malignant cells. There was a critical reliance on the quinone and imidazolium moieties but a lesser dependence on ring substituents, which served mainly to fine-tune activity. Several potent analogues were identified which, like YM155, suppressed survivin and decreased SOX2 in stem cells. The decrease in SOX2 would cause an imbalance in pluripotent factors that could potentially prompt cells to differentiate and hence decrease the risk of aberrant teratoma formation. As phosphorylation of the NF-κB p50 subunit was also suppressed, the crosstalk between phospho-p50, SOX2, and survivin could implicate a causal role for NF-κB signaling in mediating the stem cell clearing properties of dioxonaphthoimidazoliums.

NAPHTHAQUINONE METHYLTRANSFERASE INHIBITORS AND USES THEREOF

Provided herein are compounds of (I), and pharmaceutically acceptable salts, solvates, hydrates, polymorphs, co-crystals, tautomers, stereoisomers, and prodrugs thereof. Also provided are pharmaceutical compositions and methods involving the inventive compounds for the treatment of proliferative diseases (e.g., cancer (e.g., leukemia, breast cancer, melanoma, metastatic cancer) and diseases associated with inappropriate SET8 activity. Also provided are methods for inhibiting SET8 and methods for labelling SET8.

Identification of unusual C-Cl...π contacts in 2-(alkylamino)-3-chloro-1,4-naphthoquinones: Effect of N-substituents on crystal packing, fluorescence, redox and anti-microbial properties

The chemo-selective reaction of 2,3-dichloro-1,4-naphthoquinone with different primary amines affords access to a series of derivatives, such as 2-(alkylamino)-3-chloro-1,4-naphthoquinone (1-6) and 2-(benzylamino)-1,4-naphthoquinone (7), in good yields. All the compounds 1-7 were characterized thoroughly by microanalysis, standard spectroscopy and thermogravimetric methods. The supramolecular structures of 1-4 and 7 were studied by means of single-crystal X-ray diffraction to gauge the influence of substituents that are present on the amine functionality on the association of molecules in the solid state. The study showed that the introduction of various amine N-substituents induces conformational changes that apparently modify the nature and number of donor-acceptor sites for noncovalent interactions, leading to diverse crystal packing patterns. Interestingly, the introduction of 2-(benzylamino)- and 2-(2-pyridylmethylamino)- substituents in 2 and 4 successfully switched on the C-Cl...π synthon, which is scarcely seen in the crystal packing of organic molecules. Compounds 1, 2, 4 and 5 fluoresced in the range of 350-620 nm with concomitant Stokes shifts of 81, 131, 141 and 131 nm, respectively, and their cyclic voltammograms evidenced two quasi-reversible single-electron waves. All the compounds (except 5) exhibited their first endothermic peak on the DTA curves without any mass loss due to the phase change, attributable to the melting points of the respective compounds. Remarkably, compound 5 exhibited an enhanced antibacterial activity against S. aureus and proved to be a more potent antibacterial agent than the well-known drug "ciprofloxacin".

Antiproliferative, DNA intercalation and redox cycling activities of dioxonaphtho[2,3-d]imidazolium analogs of YM155: A structure-activity relationship study

The anticancer agent YM155 is widely investigated as a specific survivin suppressant. More recently, YM155 was found to induce DNA damage and this has raised doubts as to whether survivin is its primary target. In an effort to assess the contribution of DNA damage to the anticancer activity of YM155, several analogs were prepared and evaluated for antiproliferative activity on malignant cells, participation in DNA intercalation and free radical generation by redox cycling. The intact positively charged scaffold was found to be essential for antiproliferative activity and intercalation but was less critical for redox cycling where the minimal requirement was a pared down bicyclic quinone. Side chain requirements at the N1 and N3 positions of the scaffold were more alike for redox cycling and intercalation than antiproliferative activity, underscoring yet again, the limited structural overlaps for these activities. Furthermore, antiproliferative activities were poorly correlated to DNA intercalation and redox cycling. Potent antiproliferative activity (IC50 9-23 nM), exceeding that of YM155, was found for a minimally substituted methyl analog AB7. Like YM155 and other dioxonaphthoimidazoliums, AB7 was a modest DNA intercalator but with weak redox cycling activity. Thus, the capacity of this scaffold to inflict direct DNA damage leading to cell death may not be significant and YM155 should not be routinely classified as a DNA damaging agent.

Synthesis and antiplatelet, antiinflammatory, and antiallergic activities of 2-substituted 3-chloro-1,4-naphthoquinone derivatives

A series of 2-substituted 3-chloro-1,4-naphthoquinones was synthesized, and the antiplatelet, antiinflammatory, and antiallergic activities of these compounds were evaluated. The structure-activity relationships in this series were also examined. Most of the 2-alkyl/arylcarboxamido derivatives of 3-chloro-1,4-naphthoquinone showed potent activities with similar trends in each of the activities evaluated.