51439-85-1

Usage

Derivative of benzoic acid

2-(3,4-Dimethoxybenzoyl)benzoic acid is a modified version of benzoic acid.

Physical properties

White crystalline solid, melting point of around 169-171°C.

Industrial uses

Commonly used in the synthesis of various pharmaceuticals and organic compounds.

Applications

Primarily used as an intermediate in the production of dyes, pigments, and pharmaceuticals. Has potential applications in the field of materials science and organic synthesis.

Upstream product

• 37618-00-1 3-(3,4-dimethoxyphenyl)isobenzofuran-1(3H)-one 
• 75-15-0 carbon disulfide 
• 85-44-9 phthalic anhydride 
• 7446-70-0 aluminium trichloride 
• 91-16-7 1,2-dimethoxybenzene 
• 119-67-5 o-carboxybenzaldehyde 

Downstream Products

• 483-35-2 hystazarin 
• 72-48-0 1,2-dihydroxy-9,10-anthracenedione 
• 22506-55-4 2,3-dimethoxy-anthraquinone 
• 93435-26-8 2-(3,4-dimethoxybenzyl)benzoic acid 
• 860562-93-2 2-(4,5-dimethoxy-2-nitro-benzoyl)-benzoic acid 
• 137382-40-2 4-(3,4-dimethoxyphenyl)-2-phenyl-2H-phthalazin-1-one 
• 114639-49-5 methyl 2-(3,4-dimethoxybenzyl)benzoate 
• 109501-47-5 [2-(3,4-dimethoxylbenzyl)phenyl]methanol 

Relevant academic research and scientific papers

Mechanochemical Friedel-crafts acylations

Friedel-Crafts (FC) acylation reactions were exploited in the preparation of ketone-functionalized aromatics. Environmentally more friendly, solvent-free mechanochemical reaction conditions of this industrially important reaction were developed. Reaction parameters such as FC catalyst, time, ratio of reagents and milling support were studied to establish the optimal reaction conditions. The scope of the reaction was explored by employment of different aromatic hydrocarbons in conjunction with anhydrides and acylation reagents. It was shown that certain FC-reactive aromatics could be effectively functionalized by FC acylations carried out under ball-milling conditions without the presence of a solvent. The reaction mechanism was studied by in situ Raman and ex situ IR spectroscopy.

Synthesis and evaluation of analogs of the phenylpyridazinone NPD-001 as potent trypanosomal TbrPDEB1 phosphodiesterase inhibitors and in vitro trypanocidals

Trypanosomal phosphodiesterases B1 and B2 (TbrPDEB1 and TbrPDEB2) play an important role in the life cycle of Trypanosoma brucei, the causative parasite of human African trypanosomiasis (HAT), also known as African sleeping sickness. Knock down of both enzymes leads to cell cycle arrest and is lethal to the parasite. Recently, we reported the phenylpyridazinone, NPD-001, with low nanomolar IC50 values on both TbrPDEB1 (IC50: 4 nM) and TbrPDEB2 (IC50: 3 nM) (J. Infect. Dis. 2012, 206, 229). In this study, we now report on the first structure activity relationships of a series of phenylpyridazinone analogs as TbrPDEB1 inhibitors. A selection of compounds was also shown to be anti-parasitic. Importantly, a good correlation between TbrPDEB1 IC50 and EC50 against the whole parasite was observed. Preliminary analysis of the SAR of selected compounds on TbrPDEB1 and human PDEs shows large differences which shows the potential for obtaining parasite selective PDE inhibitors. The results of these studies support the pharmacological validation of the Trypanosome PDEB family as novel therapeutic approach for HAT and provide as well valuable information for the design of potent TbrPDEB1 inhibitors that could be used for the treatment of this disease.

Synthesis of tetrafunctionalized pentiptycenequinones for construction of cyclic dimers with a cylindrical shape by boronate ester formation

Abstract New tetrasubstituted pentiptycenequinone derivatives 1 and 2 having two sets of diol moieties in a syn orientation were synthesized from the corresponding 2,3-disubstituted anthracene derivatives. The semicircular scaffold of these molecules is expected to be useful to create a belt-like structure having an aromatic π-wall. Indeed, the reaction of 1 with 1,4-phenylenediboronic acid or 4,4′-biphenyldiboronic acid quantitatively gave a 2:2 macrocyclic product via boronate ester formation. The efficient formation of these cyclic structures can be explained by favorable intramolecular cyclization at the final step.

Synthesis and biological evaluation of 4-arylphthalazones bearing benzenesulfonamide as anti-inflammatory and anti-cancer agents

Nine 4-arylphthalazones bearing benzenesulfonamide (2a-i) were synthesized by the condensation of the appropriate 2-aroylbenzoic acid (1a-i) and 4-hydrazinobenzenesulfonamide in ethanol. The structures of these compounds were elucidated by elemental analysis, IR, 1H NMR, 13C NMR, and MS spectroscopy. Two compounds, 2b and 2i, showed significant anti-inflammatory activity comparable to that of the standard drug celecoxib in the carrageenan-induced rat paw edema model. These compounds (2b and 2i) had selective inhibitory activity towards the COX-2 enzyme. Compound 2b had a better selectivity ratio (COX-1/COX-2) compared to that of celecoxib and can be used as a novel template for the design of selective COX-2 inhibitors. Compounds 2d and 2i were screened for their antiproliferative activity toward 60 human cancer cell lines by the National Cancer Institute (USA). The compounds 2d and 2i displayed mild activity toward the renal cancer cell line UO-31. Nine 4-arylphthalazones bearing benzenesulfonamide (2a-i) were synthesized by the condensation of the appropriate 2-aroylbenzoic acid (1a-i) and 4-hydrazinobenzenesulfonamide in ethanol. Compounds 2b and 2i showed anti-inflammatory activity comparable to that of celecoxib in the carrageenan-induced rat paw edema model. Compounds 2d and 2i were screened for their antiproliferative activity towards 60 human cancer cell lines, displaying mild activity toward the renal cancer cell line UO-31. Copyright

Synthesis, assembly, and thin film transistors of dihydrodiazapentacene: An isostructural motif for pentacene

The study below details the synthesis, assembly, and thin film transistors from dihydrodiazapentacenes. These molecules have the same molecular shape as pentacene but are much easier to prepare and have much greater environmental stability. Thin films made from the dihydrodiazapentacene behave as field effect transistors with mobilities and on/off ratios high enough to be useful in certain applications. X-ray diffraction and AFM experiments on these films show that the molecules stack in layers with their long axis upright from the surface. Some of the derivatives synthesized for this study have unexpectedly high solubility in polar solvents such as DMF and DMSO. The crystal structure from DMF reveals self-assembled channels with each of the aniline functionalities forming a hydrogen bond with solvent. In more nonpolar solvents, the solid-state assembly switches to a herringbone motif characteristic of the linear acenes.

Novel selective PDE4 inhibitors. 1. Synthesis, structure-activity relationships, and molecular modeling of 4-(3,4-dimethoxyphenyl)-2H-phthalazin-1-ones and analogues

A number of 6-(3,4-dimethoxyphenyl)-4,5-dihydro-2H-pyridazin-3-ones and a novel series of 4-(3,4-dimethoxyphenyl)-2H-phthalazin-1-ones were prepared and tested on the cGMP-inhibited phosphodiesterase (PDE3) and cAMP-specific phosphodiesterase (PDE4) enzymes. All tested compounds were found to specifically inhibit PDE4 except for pyridazinone 3b, which showed moderate PDE4 (pIC50 = 6.5) as well as PDE3 (pIC50 = 6.6) inhibitory activity. In both the pyridazinone and phthlazinone series it was found that N-substitution is beneficial for PDE4 inhibition, whereas in the pyridazinone series it also accounts for PDE4 selectivity. In the phthalazinone series, the cis-4a,5,6,7,8,8a-hexahydrophthalazinones and their corresponding 4a,5,8,8a-tetrahydro analogues showed potent PDE4 inhibitory potency (10/11c,d: pIC50 = 7.6-8.4). A molecular modeling study revealed that the cis-fused cyclohexa(e)ne rings occupy a region in space different from that occupied by the other fused (un)saturated hydrocarbon rings applied; we therefore assume that the steric interactions of these rings with the binding site play an important role in enzyme inhibition.

Phthalazinones

Phthalazinones of the formula I in which R1 is 1-4C alkoxy or 1-4C alkoxy substituted by fluorine, R2 is halogen or (cyclo)alkoxy, and R3 is -CnH2n-C(O)R4. These compounds are suitable as bronchial therapeutics and for the treatment of dermatoses.

Synthesis and Structure - Activity Relationships of Sweet 2-Benzoylbenzoic Acid Derivatives

Twenty-four analogues of the sweet compound 2-(4-methoxybenzoyl)benzoic acid 1 were synthesized and tasted. The structure-sweet taste relationships were studied by means of principal component analysis and by comparison with the existing sweet receptor models. Three possible glucophores were identified, which could correspond to the sites B, E1, and E2 of the Tinti - Nofre model. Some similarities between this class of compounds and isovanillic sweeteners were found.

1H and 13C NMR studies of some anthraquinones and anthracenetetrones

1H and 13C NMR chemical shifts are reported and assigned for 1,4,9,10- and 2,3,9,10-anthracenetetrone. In addition, NMR data are given for 2,3-dihydroxy-9, 10-anthraquinone, 2,3-dimethoxy-9,10-anthraquinone and 1-hydroxy-2-acetoxy-9,10-anthraquinone, encountered during the preparation of the anthracenetetrones.