Category: 1877-71-0

Cao, Jiangying published the artcileDevelopment of a bestatin-SAHA hybrid with dual inhibitory activity against APN and HDAC, Product Details of C9H8O4, the publication is Molecules (2020), 25(21), 4991, database is CAplus and MEDLINE.

With five histone deacetylase (HDAC) inhibitors approved for cancer treatment, proteolysis-targeting chimeras (PROTACs) for degradation of HDAC are emerging as an alternative strategy for HDAC-targeted therapeutic intervention. Herein, three bestatin-based hydroxamic acids (P1, P2 and P3) were designed, synthesized and biol. evaluated to see if they could work as HDAC degrader by recruiting cellular inhibitor of apoptosis protein 1 (cIAP1) E3 ubiquitin ligase. Among the three compounds, the bestatin-SAHA hybrid P1 exhibited comparable even more potent inhibitory activity against HDAC1, HDAC6 and HDAC8 relative to the approved HDAC inhibitor SAHA. It is worth noting that although P1 could not lead to intracellular HDAC degradation after 6 h of treatment, it could dramatically decrease the intracellular levels of HDAC1, HDAC6 and HDAC8 after 24 h of treatment. Intriguingly, the similar phenomenon was also observed in the HDAC inhibitor SAHA. Cotreatment with proteasome inhibitor bortezomib could not reverse the HDAC decreasing effects of P1 and SAHA, confirming that their HDAC decreasing effects were not due to protein degradation Moreover, all three bestatin-based hydroxamic acids P1, P2 and P3 exhibited more potent aminopeptidase N (APN, CD13) inhibitory activities than the approved APN inhibitor bestatin, which translated to their superior anti-angiogenic activities. Taken together, a novel bestatin-SAHA hybrid was developed, which worked as a potent APN and HDAC dual inhibitor instead of a PROTAC.

Molecules published new progress about 1877-71-0. 1877-71-0 belongs to esters-buliding-blocks, auxiliary class Carboxylic acid,Benzene,Ester, name is 3-(Methoxycarbonyl)benzoic acid, and the molecular formula is C9H8O4, Product Details of C9H8O4.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Sun, Guo-Quan published the artcileNickel-catalyzed electrochemical carboxylation of unactivated aryl and alkyl halides with CO₂, Formula: C9H8O4, the publication is Nature Communications (2021), 12(1), 7086, database is CAplus and MEDLINE.

A general and practical electro-reductive Ni-catalytic system, realizing the electrocatalytic carboxylation of unactivated aryl chlorides and alkyl bromides with CO₂ were reported. A variety of unactivated aryl bromides, iodides and sulfonates can also undergo such a reaction smoothly. Notably, realized the catalytic electrochem. carboxylation of aryl (pseudo)halides with CO₂ avoiding the use of sacrificial electrodes. Moreover, this sustainable and economic strategy with electron as the clean reductant features mild conditions, inexpensive catalyst, safe and cheap electrodes, good functional group tolerance and broad substrate scope. Mechanistic investigations indicated that the reaction might proceed via oxidative addition of aryl halides to Ni(0) complex, the reduction of aryl-Ni(II) adduct to the Ni(I) species and following carboxylation with CO₂.

Nature Communications published new progress about 1877-71-0. 1877-71-0 belongs to esters-buliding-blocks, auxiliary class Carboxylic acid,Benzene,Ester, name is 3-(Methoxycarbonyl)benzoic acid, and the molecular formula is C10H20O2, Formula: C9H8O4.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Gao, Tianfeng published the artcileTargeting dihydrofolate reductase: Design, synthesis and biological evaluation of novel 6-substituted pyrrolo[2,3-d]pyrimidines as nonclassical antifolates and as potential antitumor agents, Related Products of esters-buliding-blocks, the publication is European Journal of Medicinal Chemistry (2019), 329-340, database is CAplus and MEDLINE.

A novel series of 6-substituted pyrrolo[2,3-d]pyrimidines with reversed amide moieties from the lead compound I (R = 4-pyridyl) were designed and synthesized as nonclassical antifolates and as potential antitumor agents. Target compounds II were successfully obtained through two sequential condensation reactions from the key intermediate 2-amino-6-(2-aminoethyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one. In preliminary antiproliferation assay, all compounds demonstrated submicromolar to nanomolar inhibitory effects against KB tumor cells, whereas compounds I (R = 2-, 3-, 4-pyridyl) also exhibited nanomolar antiproliferative activities toward SW620 and A549 cells. In particular, compounds I (R = 2-, 3-, 4-pyridyl) were significantly more potent than the pos. control methotrexate (MTX) and pemetrexed (PMX) to A549 cells. The growth inhibition induced cell cycle arrest at G1-phase with S-phase suppression. Along with the results of nucleoside protection assays, inhibition assays of dihydrofolate reductase (DHFR) clearly elucidated that the intracellular target of the designed compounds was DHFR. Mol. modeling studies suggested two binding modes of the target compounds with DHFR.

European Journal of Medicinal Chemistry published new progress about 1877-71-0. 1877-71-0 belongs to esters-buliding-blocks, auxiliary class Carboxylic acid,Benzene,Ester, name is 3-(Methoxycarbonyl)benzoic acid, and the molecular formula is C9H8O4, Related Products of esters-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Dai, Huimin published the artcileSolvent-Controlled, Tunable β-OAc and β-H Elimination in Rh(III)-Catalyzed Allyl Acetate and Aryl Amide Coupling via C-H Activation, Name: 3-(Methoxycarbonyl)benzoic acid, the publication is Organic Letters (2016), 18(14), 3410-3413, database is CAplus and MEDLINE.

The Heck reaction between arenes and allyl acetate led to cinnamyl derivatives and allyl products depending on the regioselectivity of β-elimination. The regioselectivity can be controlled by the solvent in the Rh(III)-catalyzed arene-allyl acetate coupling via C-H activation: (1) in THF, cinnamyl derivatives via β-H elimination were generated; (2) in MeOH, allyl products via β-OAc elimination were produced. Both routes have advantages such as excellent γ-selectivity toward allyl acetate, good to excellent yields, and broad substrate scope.

Organic Letters published new progress about 1877-71-0. 1877-71-0 belongs to esters-buliding-blocks, auxiliary class Carboxylic acid,Benzene,Ester, name is 3-(Methoxycarbonyl)benzoic acid, and the molecular formula is C9H8O4, Name: 3-(Methoxycarbonyl)benzoic acid.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Zhang, Muliang published the artcileDeoxygenative Deuteration of Carboxylic Acids with D₂O, Product Details of C9H8O4, the publication is Angewandte Chemie, International Edition (2019), 58(1), 312-316, database is CAplus and MEDLINE.

C1-Deuterated aryl and alkyl aldehydes such as 4-PhC₆H₄CDO and PhCH₂CH₂CDO were prepared chemoselectively with 58-96% deuterium incorporation by reduction of aromatic and aliphatic carboxylic acids using iridium photocatalysts, either Ph₃P or Ph₂OEt as an oxygen acceptor, 2,4,6-i-Pr₃C₆H₂SH as a hydrogen atom donor, and using D₂O as an inexpensive deuterium source. The method was used for the preparation of deuterated derivatives of pharmaceuticals and natural products containing aromatic carboxylic acid moieties. The method was also used for chemoselective reduction of aryl and alkyl carboxylic acids to the corresponding aldehydes using H₂O as a hydrogen atom source.

Angewandte Chemie, International Edition published new progress about 1877-71-0. 1877-71-0 belongs to esters-buliding-blocks, auxiliary class Carboxylic acid,Benzene,Ester, name is 3-(Methoxycarbonyl)benzoic acid, and the molecular formula is C11H21BF4N2O2, Product Details of C9H8O4.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Hang, Wei published the artcileCobalt-Catalyzed Reductive Carboxylation of Aryl Bromides with Carbon Dioxide, Recommanded Product: 3-(Methoxycarbonyl)benzoic acid, the publication is Advanced Synthesis & Catalysis (2020), 362(12), 2337-2341, database is CAplus.

Cobalt-catalyzed reductive carboxylation of aryl bromides with carbon dioxide to form the corresponding carboxylic acids ArC(O)OH [Ar = Ph, 4-MeOC₆H₄, 1-naphthyl, etc.] in good to high yields was developed. The reaction proceeded under one atm pressure of CO₂ at 40°C in the presence of cobalt iodide/2,2′-bipyridine catalysts and zinc dust as a reducing reagent. Preliminary mechanistic experiments ruled out intervention of intermediate organozinc species for carboxylation with CO₂, thus suggested direct CO₂ insertion into the corresponding ArCoBr species.

Advanced Synthesis & Catalysis published new progress about 1877-71-0. 1877-71-0 belongs to esters-buliding-blocks, auxiliary class Carboxylic acid,Benzene,Ester, name is 3-(Methoxycarbonyl)benzoic acid, and the molecular formula is C9H8O4, Recommanded Product: 3-(Methoxycarbonyl)benzoic acid.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Ren, Shi-Chao published the artcileCarbene and photocatalyst-catalyzed decarboxylative radical coupling of carboxylic acids and acyl imidazoles to form ketones, Safety of 3-(Methoxycarbonyl)benzoic acid, the publication is Nature Communications (2022), 13(1), 2846, database is CAplus and MEDLINE.

The carbene and photocatalyst co-catalyzed radical coupling of acyl electrophile and a radical precursor is emerging as attractive method for ketone synthesis. However, previous reports mainly limited to prefunctionalized radical precursors and two-component coupling. Herein, an N-heterocyclic carbene and photocatalyst catalyzed decarboxylative radical coupling of carboxylic acids and acyl imidazoles is disclosed, in which the carboxylic acids are directly used as radical precursors. The acyl imidazoles could also be generated in situ by reaction of a carboxylic acid with CDI thus furnishing a formally decarboxylative coupling of two carboxylic acids. In addition, the reaction is successfully extended to three-component coupling by using alkene as a third coupling partner via a radical relay process. The mild conditions, operational simplicity, and use of carboxylic acids as the reacting partners make our method a powerful strategy for construction of complex ketones from readily available starting materials, and late-stage modification of natural products and medicines.

Nature Communications published new progress about 1877-71-0. 1877-71-0 belongs to esters-buliding-blocks, auxiliary class Carboxylic acid,Benzene,Ester, name is 3-(Methoxycarbonyl)benzoic acid, and the molecular formula is C9H8O4, Safety of 3-(Methoxycarbonyl)benzoic acid.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Jiang, Min published the artcileVisible-Light-Induced Decarboxylative Iodination of Aromatic Carboxylic Acids, Quality Control of 1877-71-0, the publication is Synlett (2018), 29(12), 1572-1577, database is CAplus.

A convenient, efficient and practical visible-light-induced decarboxylative iodination of aromatic carboxylic acids was developed, and the corresponding aryl iodides were obtained in good yields. The method showed some advantages including the use of readily available aromatic carboxylic acids as the starting materials, simple and mild conditions, high efficiency, wide substrate scope and tolerance of various functional groups.

Synlett published new progress about 1877-71-0. 1877-71-0 belongs to esters-buliding-blocks, auxiliary class Carboxylic acid,Benzene,Ester, name is 3-(Methoxycarbonyl)benzoic acid, and the molecular formula is C9H8O4, Quality Control of 1877-71-0.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Wang, Jing-Wen published the artcileDegradation of dimethyl phthalate esters by a filamentous fungus Aspergillus versicolor isolated from deep-sea sediments, Synthetic Route of 1877-71-0, the publication is Botanica Marina (2017), 60(3), 351-359, database is CAplus.

Di-Me phthalate esters (DMPEs), which belong to phthalate esters (PAEs), are widely distributed environmental pollutants with endocrine-disrupting toxicity. The present study focused on a filamentous fungus capable of degrading DMPEs isolated from deep-sea sediments of the Indian Ocean at a water depth of 3300 m using an enrichment culture technique. The filamentous fungus was identified as Aspergillus versicolor IR-M4 based on internal transcribed spacer gene sequence anal. The degradation pathways of three isomers of DMPEs [dimethyl phthalate (DMP), di-Me isophthalate (DMI) and di-Me terephthalate (DMT)] were investigated with this marine fungus. The results showed that A. versicolor IR-M4 was able to degrade DMI to monomethyl isophthalate (MMI) from an initial concentration of 21.52 mg l^-1 to undetectable in 2 days of incubation, but without the ability for further degradation of MMI. The marine fungus also conducted sequential cleavage of the ester bonds of DMT to terephthalic acid (TA) via monomethyl terephthalate, and TA was the final end product and was resistant to further metabolism However, this marine fungus was not able to degrade DMP. The different metabolic pathways of the three DMPE isomers by the fungus suggest that the phthalate esterases produced by A. versicolor IR-M4 have a very high substrate specificity for DMPEs and monomethyl phthalate esters (MMPEs).

Botanica Marina published new progress about 1877-71-0. 1877-71-0 belongs to esters-buliding-blocks, auxiliary class Carboxylic acid,Benzene,Ester, name is 3-(Methoxycarbonyl)benzoic acid, and the molecular formula is C12H10FeO4, Synthetic Route of 1877-71-0.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Zhang, Muliang published the artcileA general deoxygenation approach for synthesis of ketones from aromatic carboxylic acids and alkenes, Application In Synthesis of 1877-71-0, the publication is Nature Communications (2018), 9(1), 1-10, database is CAplus and MEDLINE.

The construction of an aryl ketone structural unit by means of catalytic carbon-carbon coupling reactions represents the state-of-the-art in organic chem. Herein we achieved the direct deoxygenative ketone synthesis in aqueous solution from readily available aromatic carboxylic acids and alkenes, affording structurally diverse ketones I (FG = 4-Me, 4-Ph, 4-BnO, etc.) in moderate to good yields. Visible-light photoredox catalysis enables the direct deoxygenation of acids as acyl sources with triphenylphosphine and represents a distinct perspective on activation. The synthetic robustness is supported by the late-stage modification of several pharmaceutical compounds and complex mols. This ketone synthetic strategy is further applied to the synthesis of the drug zolpidem in three steps with 50% total yield and a concise construction of cyclophane-braced 18-20 membered macrocycloketones. It represents not only the advancement for the streamlined synthesis of aromatic ketones from feedstock chems., but also a photoredox radical activation mode beyond the redox potential of carboxylic acids.

Nature Communications published new progress about 1877-71-0. 1877-71-0 belongs to esters-buliding-blocks, auxiliary class Carboxylic acid,Benzene,Ester, name is 3-(Methoxycarbonyl)benzoic acid, and the molecular formula is C9H13BO3, Application In Synthesis of 1877-71-0.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics