M.W=300-350 | Heterocyclic Building Block-benzofuran

Gawlik, Maciej’s team published research in Journal of Pharmaceutical and Biomedical Analysis in 186 | CAS: 372941-54-3

Journal of Pharmaceutical and Biomedical Analysis published new progress about 372941-54-3. 372941-54-3 belongs to benzofurans, auxiliary class Other Aliphatic Heterocyclic,Fluoride,Nitrile,Amine,Benzene,Ester, name is 1-(3-(Dimethylamino)propyl)-1-(4-fluorophenyl)-3-oxo-1,3-dihydroisobenzofuran-5-carbonitrile, and the molecular formula is C20H19FN2O2, Product Details of C20H19FN2O2.

Gawlik, Maciej published the artcileIdentification and characterization of citalopram new metabolites with the use of UHPLC-Q-TOF technique: In silico toxicity assessment of the identified transformation products, Product Details of C20H19FN2O2, the publication is Journal of Pharmaceutical and Biomedical Analysis (2020), 113299, database is CAplus and MEDLINE.

In this study the metabolite profiling of citalopram with the use of human liver microsomes as well as the complementary photocatalytic method were established. This strategy allowed the detection of five metabolites of citalopram including 3-hydroxycitalopram and 3-oxocitalopram which were found as a new and not previously described metabolites of this drug The photocatalytic simulation of metabolism was carried out using tungsten (VI) oxide nanopowders with the different particle sizes, which allowed to examine the effect of this photocatalyst parameter on the mapping of metabolic processes. The accurate characterization of all observed structures was possible due to the use of ultra-high-pressure liquid chromatog. and high-resolution mass spectrometry combined system as a highly useful technique in drug metabolism studies. In order to perform the toxicity prediction of citalopram and its metabolites, the acute toxicity to rodents, as well as genotoxicity, carcinogenicity, developmental toxicity and receptor-mediated toxicity was calculated basing on the in silico tools.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem

Vedantham, Ravindra’s team published research in Organic Process Research & Development in 17 | CAS: 372941-54-3

Organic Process Research & Development published new progress about 372941-54-3. 372941-54-3 belongs to benzofurans, auxiliary class Other Aliphatic Heterocyclic,Fluoride,Nitrile,Amine,Benzene,Ester, name is 1-(3-(Dimethylamino)propyl)-1-(4-fluorophenyl)-3-oxo-1,3-dihydroisobenzofuran-5-carbonitrile, and the molecular formula is C3H5F3O, Name: 1-(3-(Dimethylamino)propyl)-1-(4-fluorophenyl)-3-oxo-1,3-dihydroisobenzofuran-5-carbonitrile.

Vedantham, Ravindra published the artcileImproved One-Pot Synthesis of Citalopram Diol and Its Conversion to Citalopram, Name: 1-(3-(Dimethylamino)propyl)-1-(4-fluorophenyl)-3-oxo-1,3-dihydroisobenzofuran-5-carbonitrile, the publication is Organic Process Research & Development (2013), 17(5), 798-805, database is CAplus.

An improved process is developed for the preparation of citalopram diol, I which involves two consecutive Grignard reactions in situ followed by an efficient and simple workup process with improved overall yield. Process development efforts for conversion of I·HBr into citalopram, II·HBr, and a control strategy for impurities are discussed. The present work addresses the challenges associated with the process development and scale-up of citalopram such as handling of unstable intermediates, control of various potential impurities, and process safety to achieve an economic and scalable process.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem

Jimenez-Holgado, Cristina’s team published research in Molecules in 26 | CAS: 372941-54-3

Molecules published new progress about 372941-54-3. 372941-54-3 belongs to benzofurans, auxiliary class Other Aliphatic Heterocyclic,Fluoride,Nitrile,Amine,Benzene,Ester, name is 1-(3-(Dimethylamino)propyl)-1-(4-fluorophenyl)-3-oxo-1,3-dihydroisobenzofuran-5-carbonitrile, and the molecular formula is C20H19FN2O2, Recommanded Product: 1-(3-(Dimethylamino)propyl)-1-(4-fluorophenyl)-3-oxo-1,3-dihydroisobenzofuran-5-carbonitrile.

Jimenez-Holgado, Cristina published the artcilePhototransformation of three psychoactive drugs in presence of sedimental water extractable organic matter, Recommanded Product: 1-(3-(Dimethylamino)propyl)-1-(4-fluorophenyl)-3-oxo-1,3-dihydroisobenzofuran-5-carbonitrile, the publication is Molecules (2021), 26(9), 2466, database is CAplus and MEDLINE.

Psychoactive drugs are classified as contaminants of emerging concern but there is limited information on their fate in surface waters. Here, we studied the photodegradation of three psychoactive drugs (sertraline, clozapine, and citalopram) in the presence of organic matter (WEOM) extracted under mild conditions from sediment of Lake Pamvotis, Greece. Spectral characterization of WEOM confirmed its humic-like nature. Preliminary experiments using chem. probes showed that WEOM was able to produce oxidant triplet excited state (3WEOM*), singlet oxygen (1O2), and hydroxyl radicals under irradiation with simulated solar light. Then, WEOM at 5 mgC L^-1 was irradiated in the presence of the three drugs. It enhanced their phototransformation by a factor of 2, 4.2, and 16 for sertraline, clozapine, and citalopram, resp. The drastic inhibiting effect of 2-propanol (5 x 10^-3 M) on the reactions demonstrated that hydroxyl radical was the key intermediate responsible for drugs photodegradation A series of photoproducts were identified by ultra-high performance liquid chromatog. (UHPLC) coupled to high resolution mass spectrometry (HR-MS). The photodegradation of the three drugs proceeded through several pathways, in particular oxidations of the rings with or without O atom inclusion, N elimination, and substitution of the halogen by OH. The formation of halogenated aromatics was observed for sertraline. To conclude, sedimental natural organic matter can significantly phototransform the studied antidepressant drugs and these reactions need to be more investigated. Finally, ecotoxicity was estimated for the three target analytes and their photoproducts, using the Ecol. Structure Activity Relationships (ECOSAR) computer program.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem

Che, Minghui’s team published research in Heilongjiang Yiyao in 28 | CAS: 372941-54-3

Heilongjiang Yiyao published new progress about 372941-54-3. 372941-54-3 belongs to benzofurans, auxiliary class Other Aliphatic Heterocyclic,Fluoride,Nitrile,Amine,Benzene,Ester, name is 1-(3-(Dimethylamino)propyl)-1-(4-fluorophenyl)-3-oxo-1,3-dihydroisobenzofuran-5-carbonitrile, and the molecular formula is C20H19FN2O2, Synthetic Route of 372941-54-3.

Che, Minghui published the artcileHPLC method for determination of related substances in escitalopram oxalate citalopram tablets, Synthetic Route of 372941-54-3, the publication is Heilongjiang Yiyao (2015), 28(1), 65-69, database is CAplus.

Objective: To establish an HPLC method for determination of escitalopram oxalate citalopram on material test. Methods: The stationary phase was Agilent C₁₈ (150 mm × 4.5 mm, 5 μm); the mobile phase was (1.5 g, sodium acetate and 0.4 mL glacial acetic acid to dissolve 1 L water, adding 1 M NaOH to adjust pH 5.2 buffer) methanol and acetonitrile-buffer (33:7:60); the flow rate was 1.0 mL/min; the detection wavelength was 239 nm; and the sample quantity was 10 μL. Results: Under the chromatog. conditions, the principal components and the related materials were completely separated, and the separating degree of all impurities was in good condition. In 0.375-3 μg/mL, 0.621-4.91 μg/mL and 4.91-4.90 μg/mL, three main relevant materials had good linear relationship between peak area and concentration, and the average recovery conformed to specified requirements. Conclusion: This method is simple and reproducible and it can be used for quality control of escitalopram oxalate citalopram tablets.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem

Horsing, Maritha’s team published research in Chemosphere in 89 | CAS: 372941-54-3

Chemosphere published new progress about 372941-54-3. 372941-54-3 belongs to benzofurans, auxiliary class Other Aliphatic Heterocyclic,Fluoride,Nitrile,Amine,Benzene,Ester, name is 1-(3-(Dimethylamino)propyl)-1-(4-fluorophenyl)-3-oxo-1,3-dihydroisobenzofuran-5-carbonitrile, and the molecular formula is C20H19FN2O2, Application of 1-(3-(Dimethylamino)propyl)-1-(4-fluorophenyl)-3-oxo-1,3-dihydroisobenzofuran-5-carbonitrile.

Horsing, Maritha published the artcileFate of citalopram during water treatment with O₃, ClO₂, UV and fenton oxidation, Application of 1-(3-(Dimethylamino)propyl)-1-(4-fluorophenyl)-3-oxo-1,3-dihydroisobenzofuran-5-carbonitrile, the publication is Chemosphere (2012), 89(2), 129-135, database is CAplus and MEDLINE.

In the present study we investigate the fate of citalopram (CIT) at neutral pH using advanced water treatment technologies that include O₃, ClO₂ oxidation, UV irradiation and Fenton oxidation The ozonation resulted in 80% reduction after 30 min treatment. Oxidation with ClO₂ removed >90% CIT at a dosage of 0.1 mg L^-1. During UV irradiation 85% reduction was achieved after 5 min, while Fenton with addition of 14 mg L^-1 (Fe²⁺) resulted in 90% reduction of CIT. During these treatment experiments transformation products (TPs) were formed from CIT, where five compounds were identified by using high resolution and tandem mass spectrometry. Among these desmethyl-citalopram and citalopram N-oxide have been previously identified as human metabolites, while three are novel and published here for the first time. The three TPs are a hydroxylated dimethylamino-side chain derivative, a butyrolactone derivative and a defluorinated derivative of CIT.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem

Osawa, Rodrigo A.’s team published research in Chemosphere in 217 | CAS: 372941-54-3

Chemosphere published new progress about 372941-54-3. 372941-54-3 belongs to benzofurans, auxiliary class Other Aliphatic Heterocyclic,Fluoride,Nitrile,Amine,Benzene,Ester, name is 1-(3-(Dimethylamino)propyl)-1-(4-fluorophenyl)-3-oxo-1,3-dihydroisobenzofuran-5-carbonitrile, and the molecular formula is C20H19FN2O2, Safety of 1-(3-(Dimethylamino)propyl)-1-(4-fluorophenyl)-3-oxo-1,3-dihydroisobenzofuran-5-carbonitrile.

Osawa, Rodrigo A. published the artcileTransformation products of citalopram: Identification and in-silico toxicological assessment, Safety of 1-(3-(Dimethylamino)propyl)-1-(4-fluorophenyl)-3-oxo-1,3-dihydroisobenzofuran-5-carbonitrile, the publication is Chemosphere (2019), 858-868, database is CAplus and MEDLINE.

The objective of this study was to identify transformation products (TPs) of citalopram (CIT), an antidepressant drug, in laboratory experiments Moreover, toxicity predictions and analyzes in wastewater samples were performed. For the formation of TPs, raw water was used for the processes of hydrolysis; photodegradation under UV irradiation and chlorination. The toxicities were predicted by computational toxicity assessment. The TPs were identified by liquid chromatog. quadrupole time-of-flight mass spectrometry (LC-QTOF/MS) in broadband collision induced dissociation (bbCID) acquisition mode and product ion scan mode (MS/MS). The probable structures of the TPs under study were established based on accurate mass, fragmentations observed in the MS spectra and prediction tools software. The experiments resulted in seventeen possible identified TPs and their stability and formation was monitored over time in the experiments Two of these TPs were identified in wastewater samples It was also observed that most of TPs formed were either less toxic then CIT or had a similar toxicity.

Chemosphere published new progress about 372941-54-3. 372941-54-3 belongs to benzofurans, auxiliary class Other Aliphatic Heterocyclic,Fluoride,Nitrile,Amine,Benzene,Ester, name is 1-(3-(Dimethylamino)propyl)-1-(4-fluorophenyl)-3-oxo-1,3-dihydroisobenzofuran-5-carbonitrile, and the molecular formula is C20H19FN2O2, Safety of 1-(3-(Dimethylamino)propyl)-1-(4-fluorophenyl)-3-oxo-1,3-dihydroisobenzofuran-5-carbonitrile.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem

Nika, Maria-Christina’s team published research in Journal of Hazardous Materials in 419 | CAS: 372941-54-3

Journal of Hazardous Materials published new progress about 372941-54-3. 372941-54-3 belongs to benzofurans, auxiliary class Other Aliphatic Heterocyclic,Fluoride,Nitrile,Amine,Benzene,Ester, name is 1-(3-(Dimethylamino)propyl)-1-(4-fluorophenyl)-3-oxo-1,3-dihydroisobenzofuran-5-carbonitrile, and the molecular formula is C20H19FN2O2, Quality Control of 372941-54-3.

Nika, Maria-Christina published the artcileNon-target trend analysis for the identification of transformation products during ozonation experiments of citalopram and four of its biodegradation products, Quality Control of 372941-54-3, the publication is Journal of Hazardous Materials (2021), 126401, database is CAplus and MEDLINE.

During ozonation in wastewater treatment plants, ozone reacts with emerging pollutants, which are partially removed through the secondary treatment, as long as, with their biotransformation products, triggering the formation of ozonation transformation products (TPs). Although the transformation of parent compounds (PCs) and their metabolites has been reported in the literature, the probable transformation of biotransformation products has not been investigated so far. This study evaluates the fate of citalopram (CTR) and four of its biotransformation products (DESCTR, CTRAM, CTRAC and CTROXO) during ozonation experiments A Gaussian curve-based trend anal. was performed for the first time for the automated detection of TPs in ozone concentrations ranging from 0.06 to 12 mg/L. In total 46 ozonation TPs were detected; 7 TPs of CTR, 10 of DESCTR, 9 of CTRAM, 12 of CTRAC and 8 of CTROXO and were structurally elucidated based on their high resolution tandem mass spectra interpretation and tandem mass spectra similarity with the resp. PC. Results have demonstrated that the examined compounds follow common transformation pathways in reaction with ozone and that common TPs were formed through the ozonation of different structurally-alike compounds Moreover, the toxicity of the identified TPs was predicted with an inhouse risk assessment program.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem