Category: 1877-71-0

Zogota, Rimants published the artcilePeptidomimetic plasmepsin inhibitors with potent anti-malarial activity and selectivity against cathepsin D, Safety of 3-(Methoxycarbonyl)benzoic acid, the publication is European Journal of Medicinal Chemistry (2019), 344-352, database is CAplus and MEDLINE.

Following up the open initiative of anti-malarial drug discovery, a GlaxoSmithKline (GSK) phenotypic screening hit was developed to generate hydroxyethylamine based plasmepsin (Plm) inhibitors exhibiting growth inhibition of the malaria parasite Plasmodium falciparum at nanomolar concentrations Lead optimization studies were performed with the aim of improving Plm inhibition selectivity vs. the related human aspartic protease cathepsin D (Cat D). Optimization studies were performed using Plm IV as a readily accessible model protein, the inhibition of which correlates with anti-malarial activity. Guided by sequence alignment of Plms and Cat D, selectivity-inducing structural motifs were modified in the S3 and S4 sub-pocket occupying substituents of the hydroxyethylamine inhibitors. This resulted in potent anti-malarials with an up to 50-fold Plm IV/Cat D selectivity factor. More detailed investigation of the mechanism of action of the selected compounds revealed that they inhibit maturation of the P. falciparum subtilisin-like protease SUB1, and also inhibit parasite egress from erythrocytes. Our results indicate that the anti-malarial activity of the compounds is linked to inhibition of the SUB1 maturase plasmepsin subtype Plm X.

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 C18H24N6O6S4, Safety of 3-(Methoxycarbonyl)benzoic acid.

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

Heimburg, Tino published the artcileStructure-Based Design and Biological Characterization of Selective Histone Deacetylase 8 (HDAC8) Inhibitors with Anti-Neuroblastoma Activity, COA of Formula: C9H8O4, the publication is Journal of Medicinal Chemistry (2017), 60(24), 10188-10204, database is CAplus and MEDLINE.

Histone deacetylases (HDACs) are important modulators of epigenetic gene regulation and addnl. control the activity of non-histone protein substrates. While for HDACs 1-3 and 6 many potent selective inhibitors have been obtained, for other subtypes much less is known on selective inhibitors and the consequences of their inhibition. The present report describes the development of substituted benzhydroxamic acids as potent and selective HDAC8 inhibitors. Docking studies using available crystal structures have been used for structure-based optimization of this series of compounds Within this study, the authors have investigated the role of HDAC8 in the proliferation of cancer cells and optimized hits for potency and selectivity, both in vitro and in cell culture. The combination of structure-based design, synthesis, and in vitro screening to cellular testing resulted in potent and selective HDAC8 inhibitors that showed anti-neuroblastoma activity in cellular testing.

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, COA of Formula: C9H8O4.

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

Lutter, Ferdinand H. published the artcileFacile Conversion of Molecularly Complex (Hetero)aryl Carboxylic Acids into Alkynes for Accelerated SAR Exploration, Category: esters-buliding-blocks, the publication is Chemistry – A European Journal (2021), 27(60), 14816-14820, database is CAplus and MEDLINE.

Herein, a functional-group-tolerant and operationally simple decarbonylative alkynylation that allows the conversion of complex (hetero)aryl carboxylic acids into alkynes were reported. Furthermore, the utility of this method was demonstrated in the preparation of a triazolo analog of the com. drug moclobemide. Lastly, mechanistic investigations using labeled carboxylic acid derivatives clearly show the decarbonylative nature of this transformation.

Chemistry – A European Journal 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, Category: esters-buliding-blocks.

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

Wang, Yanwei published the artcileCobalt-catalyzed carboxylation of aryl and vinyl chlorides with CO₂, Synthetic Route of 1877-71-0, the publication is Chemical Communications (Cambridge, United Kingdom) (2020), 56(92), 14416-14419, database is CAplus and MEDLINE.

The transition-metal-catalyzed carboxylation of aryl and vinyl chlorides with CO₂ is rarely studied, and has been achieved only with a Ni catalyst or combination of palladium and photoredox. In this work, the cobalt-catalyzed carboxylation of aryl and vinyl chlorides and bromides with CO₂ has been developed. These transformations proceed under mild conditions and exhibit a broad substrate scope, affording the corresponding carboxylic acids in good to high yields.

Chemical Communications (Cambridge, United Kingdom) 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 C23H23ClN2O4, Synthetic Route of 1877-71-0.

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

Zeng, Linwei published the artcilePhoto-induced synthesis of β-sulfonyl imides from carboxylic acids, Formula: C9H8O4, the publication is Chemical Communications (Cambridge, United Kingdom) (2021), 57(55), 6792-6795, database is CAplus and MEDLINE.

A photo-induced imidation process of carboxylic acids is described. Numerous carboxylic acids could convert to β-sulfonyl imides in the presence of N-sulfonyl ynamides under visible light irradiation Control experiments and mechanistic studies demonstrate that this imidation process involves a hydroacyloxylation/radical rearrangement cascade. This protocol represents a direct imidation method from carboxylic acids under mild conditions, with broad scope and high atom-economy.

Chemical Communications (Cambridge, United Kingdom) 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 C7H5I2NO3, Formula: C9H8O4.

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

Weis, Erik published the artcileIr^III-Catalyzed Selective ortho-Monoiodination of Benzoic Acids with Unbiased C-H Bonds, COA of Formula: C9H8O4, the publication is Chemistry – A European Journal (2020), 26(45), 10185-10190, database is CAplus and MEDLINE.

An iridium-catalyzed selective ortho-monoiodination of benzoic acids with two equivalent C-H bonds was presented. A wide range of electron-rich and electron-poor substrates underwent the reaction under mild conditions, with >20:1 mono/di selectivity. Importantly, the C-H iodination occurred selectively ortho to the carboxylic acid moiety in substrates bearing competing coordinating directing groups. The reaction was performed at room temperature and no inert atm. or exclusion of moisture was required. Mechanistic investigations revealed a substrate-dependent reversible C-H activation/protodemetalation step, a substrate-dependent turnover-limiting step and the crucial role of the AgI additive in the deactivation of the iodination product towards further reaction.

Chemistry – A European Journal 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 C15H14BNO4S, COA of Formula: C9H8O4.

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

Weis, Erik published the artcileLate-Stage Amination of Drug-Like Benzoic Acids: Access to Anilines and Drug Conjugates through Directed Iridium-Catalyzed C-H Activation, Formula: C9H8O4, the publication is Chemistry – A European Journal (2021), 27(72), 18188-18200, database is CAplus and MEDLINE.

The method presented herein enables the amination of a wide array of benzoic acids RC(O)OH (R = 2-fluorophenyl, naphthalen-1-yl, thiophen-2-yl, 2H-1,3-benzodioxol-4-yl, etc.) with high selectivity. The robustness of the system is manifested by the large number of functional groups tolerated, which allowed the amination of a diverse array of marketed drugs and drug-like mols. Furthermore, the introduction of a synthetic handle enabled expeditious access to targeted drug-delivery conjugates, e.g., I, PROTACs II, and probes for chem. biol. This rapid access to valuable analogs, combined with operational simplicity and applicability to high-throughput experimentation has the potential to aid and considerably accelerate drug discovery.

Chemistry – A European Journal 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 C6H5F4NO3S, Formula: C9H8O4.

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

Liu, Chengwei published the artcileBimetallic Cooperative Catalysis for Decarbonylative Heteroarylation of Carboxylic Acids via C-O/C-H Coupling, Safety of 3-(Methoxycarbonyl)benzoic acid, the publication is Angewandte Chemie, International Edition (2021), 60(19), 10690-10699, database is CAplus and MEDLINE.

Cooperative bimetallic catalysis is a fundamental approach in modern synthetic chem. We report bimetallic cooperative catalysis for the direct decarbonylative heteroarylation of ubiquitous carboxylic acids via acyl C-O/C-H coupling [e.g., benzoxazole + benzoic acid → 2-phenylbenzoxazole (92%)]. This novel catalytic system exploits the cooperative action of a copper catalyst and a palladium catalyst in decarbonylation, which enables highly chemoselective synthesis of important heterobiaryl motifs through the coupling of carboxylic acids with heteroarenes in the absence of prefunctionalization or directing groups. This cooperative decarbonylative method uses common carboxylic acids and shows a remarkably broad substrate scope (>70 examples), including late-stage modification of pharmaceuticals and streamlined synthesis of bioactive agents. Extensive mechanistic and computational studies were conducted to gain insight into the mechanism of the reaction. The key step involves intersection of the two catalytic cycles via transmetalation of the copper-aryl species with the palladium(II) intermediate generated by oxidative addition/decarbonylation.

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 C9H8O4, Safety of 3-(Methoxycarbonyl)benzoic acid.

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

Liu, Chengwei published the artcilePalladium-Catalyzed Decarbonylative Borylation of Carboxylic Acids: Tuning Reaction Selectivity by Computation, Synthetic Route of 1877-71-0, the publication is Angewandte Chemie, International Edition (2018), 57(51), 16721-16726, database is CAplus and MEDLINE.

Decarbonylative borylation of carboxylic acids is reported. Carbon electrophiles are generated directly after reagent-enabled decarbonylation of the in situ accessible sterically-hindered acyl derivative of a carboxylic acid under catalyst controlled conditions. The scope and the potential impact of this method are demonstrated in the selective borylation of a variety of aromatics (>50 examples). This strategy was used in the late-stage derivatization of pharmaceuticals and natural products. Computations reveal the mechanistic details of the unprecedented C-O bond activation of carboxylic acids. By circumventing the challenging decarboxylation, this strategy provides a general synthetic platform to access arylpalladium species for a wide array of bond formations from abundant carboxylic acids. The study shows a powerful combination of experiment and computation to predict decarbonylation selectivity.

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 C9H8O4, Synthetic Route of 1877-71-0.

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

Liu, Chengwei published the artcileSynthesis of Biaryls via Decarbonylative Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of Carboxylic Acids, Formula: C9H8O4, the publication is iScience (2019), 749-759, database is CAplus and MEDLINE.

The present report implements a decarbonylative version with loss of carbon monoxide (CO) that enables to directly engage acids ArC(O)OH (Ar¹ = 2-[(E)-2-phenylethenyl]phenyl, naphthalen-1-yl, pyridin-3-yl, etc.)/Ar¹B(OH)₂ (Ar¹ = thiophen-3-yl, naphthalen-2-yl, 2H-1,3-benzodioxol-5-yl, etc.) in a Suzuki-Miyaura cross-coupling to produce biaryls as a general method with high cross-coupling selectivity using a well-defined Pd(0)/(II) catalytic cycle. This protocol shows a remarkably broad scope (>80 examples) and is performed in the absence of exogenous inorganic bases. In a broader context, the approach shows promise for routine applications in the synthesis of biaryls Ar-Ar¹ by carefully controlled decarbonylation of prevalent acids.

iScience 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, Formula: C9H8O4.

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