19336-96-0

Upstream product

• 85-44-9 phthalic anhydride 
• 90-04-0 2-methoxy-phenylamine 
• 2314-77-4 N-(2-methoxyphenyl)phthalimide 
• 1025774-93-9 C₁₉H₂₀N₂O₄ 
• 91-23-6 2-Nitroanisole 
• 65649-49-2 diphenic anhydride 
• 88-75-5 2-hydroxynitrobenzene 

Downstream Products

• 85-44-9 phthalic anhydride 
• 90-04-0 2-methoxy-phenylamine 
• 108444-18-4 3-hydroxy-2-(2-methoxyphenyl)isoindolin-1-one 
• 2314-77-4 N-(2-methoxyphenyl)phthalimide 
• 827-27-0 sodium 1,2-benzenedicarboxylate 

Relevant academic research and scientific papers

Organotin(IV) derivatives based on 2-((2-methoxyphenyl)carbamoyl)benzoic acid: Synthesis, spectroscopic characterization, assessment of antibacterial, DNA interaction, anticancer and antileishmanial potentials

A series of ten organotin(IV) carboxylate derivatives of 2-((2-methoxyphenyl)carbamoyl)benzoic acid were prepared and confirmed by FTIR, CHN analysis and single crystal XRD (SCXRD) as well as by NMR and mass spectrometry. The microelemental CHN analysis results give a close matching with those of the theoretical values of CHN atoms. The results of the solid state SCXRD for the complex 3 reveals a trigonal bipyramidal geometry (TBG) with slight distortion for the R3SnL derivatives. Further confirmation about the 5-coordinated TBG may also be achieved from the τ value which is 0.87 for the complex 3. It is obvious from the crystal structure of the complex 3 that the involvement of the O1 of the carboxylate moiety and O3 of the amide moiety with Sn atom are responsible for formation of the polymeric structure having 5-coordinated TBG. The comparison of SCXRD value (124.8°) and that of 13C NMR value (123°) for C-Sn-C angle in complex 3 is the best confirmation of 5-coordinated TBG for the R3SnL derivatives. The evaluated compounds interact with DNA by an intercalative type of binding as displayed by the results obtained from UV-vis. and viscosity measurements. The results of the antimicrobial activity of the evaluated compounds in comparison to the standard drugs demonstrate that the tested compounds possess good antimicrobial potentials. The cytotoxicity results obtained against H-157 and BHK-21 cell lines using Sulforhodamine B based method show that compound 1 has the maximum activity among the studied compounds and its activity is comparable to that of the vincristine. The small IC50 value for the compound 1 as compared to the standard antileishmanial drug, Amphotericin B, proves the efficiency of the tested compounds for the treatment of leishmania disease.

COMPOUNDS AND METHODS FOR INDUCING CHONDROGENESIS

Described herein are compounds and compositions for the amelioration of arthritis or joint injuries by inducing mesenchymal stem cells into chondrocytes.

Aza-DielsAlder reaction between N-aryl-1-oxo-1H-isoindolium ions and tert-enamides: Steric effects on reaction outcome

The synthesis of 5-substituted 6,6a-dihydroisoindolo[2,1-a]quinolin-11(5H)- ones via [4 + 2] imino-DielsAlder cyclization from N-aryl-3- hydroxyisoindolinones and N-vinyl lactams under Lewis acid-catalysed anhydrous conditions is reported. Reactions of N-(2-substituted-aryl)-3- hydroxyisoindolinones with N-vinylpyrrolidone under identical conditions resulted in the formation of 2-(2-substitued-aryl)-3-(2-(2-oxopyrrolidin-1-yl) vinyl)isoindolin-1-one analogues indicating steric hinderance as the cause of deviation. The probable mechanism of the reaction based on the results from X-ray crystallography and molecular modelling is discussed.

Synthesis and biological evaluation of novel N-(alkoxyphenyl)-aminocarbonylbenzoic acid derivatives as PTP1B inhibitors

Based on the fact that petroselinic acid showed good inhibitory activity (IC50=6.99μmol/L) against protein tyrosine phophatase 1B(PTP1B) in vitro, a series of novel N-(alkoxyphenyl)-aminocarbonylbenzoic acid derivatives were designed and synthesized. The results indicated that most of the derivatives showed more potent activities against PTP1B. Especially, compound 13 had obvious activity with an IC50 of 106nmol/L in vitro.

Kinetics and mechanism of large rate enhancement in the alkaline hydrolysis of N′-morpholino-N-(2′-methoxyphenyl)phthalamide

(Chemical Equation Presented) The apparent second-order rate constant (kOH) for hydroxide-ion-catalyzed conversion of 1 to N-(2′-methoxyphenyl)phthalamate (4) is ～103-fold larger than kOH for alkaline hydrolysis of N-morpholinobenzamide (2). These results are explained in terms of the reaction scheme 1→ k1obs3→k2obs4 where 3 represents N-(2′- methoxyphenyl)phthalimide and the values of k2obs/k1obs vary from 6.0 × 102 to 17 × 102 within [NaOH] range of 5.0 × 10-3 to 2.0 M. Pseudo-first-order rate constants (kobs) for alkaline hydrolysis of 1 decrease from 21.7 × 10-3 to 15.6 × 10-3 s-1 with an increase in ionic strength (by NaCl) from 0.5 to 2.5 M at 0.5 M NaOH and 35°C. The values of kobs, obtained for alkaline hydrolysis of 2 within [NaOH] range 1.0 × 10-2 to 2.0 M at 35°C, follow the relationship kobs = kOH[HO-] + kOH′[HO -]2 with least-squares calculated values of kOH and kOH′ as (6.38 ± 0.15) × 10-5 and (4.59 ± 0.09) × 10-5 M-2 s-1, respectively. A few kinetic runs for aqueous cleavage of 1, N′-morpholino- N-(2′-methoxyphenyl)-5-nitrophthalamide (5) and N′-morpholino-N- (2′-methoxyphenyl)-4-nitrophthalamide (6) at 35°C and 0.05 M NaOH as well as 0.05 M NaOD reveal the solvent deuterium kinetic isotope effect (= kobsH2O/kobsD2O) as 1.6 for 1, 1.9 for 5, and 1.8 for 6. Product characterization study on the cleavage of 5, 6, and N-(2′-methoxyphenyl)-4-nitrophthalimide (7) at 0.5 M NaOD in D 2O solvent shows the imide-intermediate mechanism as the exclusive mechanism.

Determination of pKa of ammonium and phenolic groups: Evidence of intramolecular hydrogen bonding in aqueous solution

The ionization constants of 2-hydroxyanilinium, 2-methoxyanilinium, 4-nitroanilinium ions, N-(2′-hydroxyphenyl)-phthalamic acid and N-(2′-methoxyphenyl) phthalamic acid, determined spectrophotometrically, have been rationalized in terms of internal hydrogen bonding and steric hindrance between o-substituent and reaction site.

Efficient rate enhancement due to intramolecular general base (IGB) assistance in the hydrolysis of N-(o-hydroxyphenyl)phthalimide

The rates of the hydrolyses of N-(o-hydroxyphenyl)phthalimide (1) and N-(o-methoxyphenyl)phthalimide (2), studied at different pH, show that the hydrolysis of 1 involves intramolecular general base (IGB) assistance where the o-O- group of ionized 1 acts as IGB and H2O as the reactant. The rate enhancement due to the IGB-assisted reaction of H 2O with ionized 1 is >8 × 104-fold. Pseudo-first-order rate constant for the reaction of water with 2 is ～2 × 103-fold smaller than the first-order rate constant (0.10 s-1) for pH-independent hydrolysis of 1 within the pH range of 9.60-10.10. Second-order rate constants (kOH) for hydroxide ion-assisted hydrolysis of ionized 1 and 2 are 3.0 and 29.1 M-1 s-1, respectively. The solvent deuterium kinetic isotope effect (dKIE) on the rate of alkaline hydrolysis of 1 and 2 reveals that the respective values of kOH/kOD are 0.84 and 0.78, where kOD represents the second-order rate constant for DO--assisted cleavage of these imides (1 and 2). The value of kwH2O/k dD2O is 2.04, with kwH2O and k dD2O representing pseudo-first-order rate constants for the reactions of ionized 1 with H2O and D2O, respectively.

Intramolecular carboxylic group-assisted cleavage of N-(2-hydroxyphenyl)- phthalamic acid (7) and N-(2-methoxyphenyl)-phthalamic acid (8): Absence of intramolecular general acid catalysis due to 2-OH in 7

The values of pseudo first-order rate constants (kobs) for the cleavage of AM 2-hydroxyphenyl)phthalamic acid (7), obtained at 4.9 × 10-2 M HCl, 35°C, and within CH3CN content range 2-80% (v/v) in mixed aqueous solvent are smaller than kobs for the cleavage of N-(2-methoxyphenyllphthalamic acid (8), obtained under almost similar experimental conditions, by nearly 1.5- to 2-fold. These observations show the absence of expected intramolecular general acid catalysis due to 2-OH group in 7. The values of kobs for the cleavage of 7 and 8 decrease by more than 20-fold with the increase in the content of CH3CN from 2 to 80-82% (v/v) in mixed aqueous solvent. The kinetic data reveal that in acidic aqueous cleavage of 7, N-cyclization (leading to the formation of imide) and O-cyclization (leading to the formation of phthalic anhydride) vary from ～10 to 15% and ～90 to 85%, respectively, with the increase in CH 3CN content from 2 to 80% (v/v). Similar increase in CH3CN content causes increase in N-cyclization from ～0 to 5% and decrease in O-cyclization from ～100 to 95% in the acidic aqueous cleavage of 8. Some speculative, yet conceivable, reasons for nearly 10 and 0% N-cyclization in the cleavage of respective 7 and 8 at low content of CH3CN have been described.

Reaction of cyclic anhydrides with aromatic amines: Part I - Synthesis of anilinic acids from phthalic anhydride

Some unreported anilinic acids 5a-j and 7 have been synthesised and their spectral data reported. Their in vitro insecticidal screening as protectants of maize (Zea mays) against Sitophilus zeamais shows 2-(N-naphthylcarbamoyl)benzoic acid 7 to be the most active member of the series.