Month: November 2022

Trobe, Melanie published the artcileA modular synthesis of teraryl-based α-helix mimetics, part 4: Core fragments with two halide leaving groups featuring side chains of proteinogenic amino acids, Recommanded Product: 2-Chloroacetamide, the publication is European Journal of Organic Chemistry (2022), 2022(17), e202101279, database is CAplus and MEDLINE.

Teraryl-based α-helix mimetics have proven to be useful compounds for the inhibition of protein-protein interactions (PPI). We have developed a modular and flexible approach for the synthesis of teraryl-based α-helix mimetics using a benzene core unit featuring two halide leaving groups of differentiated reactivity in the Pd-catalyzed cross-coupling used for teraryl assembly. The use of para-bromo iodoarene core fragments resolved the issue of hydrolysis during cross-coupling that was observed when using triflate as a leaving group. We report a complete set of para-bromoiodoarene core fragments decorated with side chains of all proteinogenic amino acids relevant for PPI (Ala, Arg, Asn, Asp, Cys, Gln, Glu, His, Ile, Leu, Lys, Met, Phe, Ser, Thr, Trp, Tyr and Val). In order to be compatible with general cross-coupling conditions, some of the nucleophilic side chains had to be provided in a protected form to serve as stable building blocks.

European Journal of Organic Chemistry published new progress about 79-07-2. 79-07-2 belongs to amides-buliding-blocks, auxiliary class Chloride,Amine,Aliphatic hydrocarbon chain,Amide,Inhibitor, name is 2-Chloroacetamide, and the molecular formula is C20H12N2O2, Recommanded Product: 2-Chloroacetamide.

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

Ortega, Jose-Antonio published the artcileBinding Affinities of Oligonucleotides and PNAs Containing Phenoxazine and G-Clamp Cytosine Analogues Are Unusually Sequence-Dependent, Product Details of C40H35N7O8, the publication is Organic Letters (2007), 9(22), 4503-4506, database is CAplus and MEDLINE.

Melting temperatures of DNA duplexes containing the phenoxazine (P) and G-clamp (X) cytosine analogs exhibited a strong and unusual dependence on the nucleoside flanking the modified nucleobase, and the same trend was observed in PNA-DNA duplexes incorporating X in the PNA chain. Mol. dynamics simulations of the DNA duplexes show that generalized stacking (including secondary interactions of the ammonium group of X) and hydrogen bonding are good descriptors of the different duplex stabilities.

Organic Letters published new progress about 186046-83-3. 186046-83-3 belongs to amides-buliding-blocks, auxiliary class Purine,Carboxylic acid,Amine,Benzene,Amide,Others,PNA,, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(2-(((benzhydryloxy)carbonyl)amino)-6-oxo-5H-purin-9(6H)-yl)acetamido)acetic acid, and the molecular formula is C40H35N7O8, Product Details of C40H35N7O8.

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

Collins, Jon L. published the artcileN-(2-Benzoylphenyl)-L-tyrosine PPARγ Agonists. 2. Structure-Activity Relationship and Optimization of the Phenyl Alkyl Ether Moiety, Product Details of C5H10N2OS, the publication is Journal of Medicinal Chemistry (1998), 41(25), 5037-5054, database is CAplus and MEDLINE.

We previously reported the identification of (2S)-((2-benzoylphenyl)amino)-3-{4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenyl}propanoic acid (I) (PPARγ pK_i = 8.94, PPARγ pEC₅₀ = 9.47) as a potent and selective PPARγ agonist. We now report the expanded structure-activity relationship around the Ph alkyl ether moiety by pursuing both a classical medicinal chem. approach and a solid-phase chem. approach for analog synthesis. The solution-phase strategy focused on evaluating the effects of oxazole and Ph ring replacements of the 2-(5-methyl-2-phenyloxazol-4-yl)ethyl side chain of I with several replacements providing potent and selective PPARγ agonists with improved aqueous solubility Specifically, replacement of the Ph ring of the phenyloxazole moiety with a 4-pyridyl group to give (2S)-((2-benzoylphenyl)amino)-3-{4-[2-(5-methyl-2-pyridin-4-yloxazol-4-yl)ethoxy]phenyl}propionic acid (PPARγ pK_i = 8.85, PPARγ pEC₅₀ = 8.74) or a 4-methylpiperazine to give (2S)-((2-benzoylphenyl)amino)-3-(4-{2-[5-methyl-2-(4-methylpiperazin-1-yl)thiazol-4-yl]ethoxy}phenyl)propionic acid (PPARγ pK_i = 8.66, PPARγ pEC₅₀ = 8.89) provided two potent and selective PPARγ agonists with increased solubility in pH 7.4 phosphate buffer and simulated gastric fluid as compared to I. The second strategy took advantage of the speed and ease of parallel solid-phase analog synthesis to generate a more diverse set of Ph alkyl ethers which led to the identification of a number of novel, high-affinity PPARγ ligands (PPARγ pK_i‘s 6.98-8.03). The combined structure-activity data derived from the two strategies provide valuable insight on the requirements for PPARγ binding, functional activity, selectivity, and aqueous solubility

Journal of Medicinal Chemistry published new progress about 14294-10-1. 14294-10-1 belongs to amides-buliding-blocks, auxiliary class Morpholine,Thiourea,Amine,Amide, name is Morpholine-4-carbothioamide, and the molecular formula is C5H10N2OS, Product Details of C5H10N2OS.

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

Youn, So Won published the artcilePd-Catalyzed Intramolecular Oxidative C-H Amination: Synthesis of Carbazoles, Recommanded Product: (2-Pivalamidophenyl)boronic acid, the publication is Organic Letters (2011), 13(14), 3738-3741, database is CAplus and MEDLINE.

A Pd-catalyzed oxidative C-H amination of N-Ts-2-arylanilines under ambient temperature using Oxone as an inexpensive, safe, and easy-to-handle oxidant has been developed. This process represents a green and practical method for the facile construction of carbazoles with a broad substrate scope and wide functional group tolerance.

Organic Letters published new progress about 146140-95-6. 146140-95-6 belongs to amides-buliding-blocks, auxiliary class Boronic acid and ester,Amine,Benzene,Amide,Boronic Acids,Boronic Acids,Boronic acid and ester,, name is (2-Pivalamidophenyl)boronic acid, and the molecular formula is C12H16BClO3, Recommanded Product: (2-Pivalamidophenyl)boronic acid.

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

Ghiassian, Sara published the artcileSynthesis of small water-soluble diazirine-functionalized gold nanoparticles and their photochemical modification, HPLC of Formula: 360-92-9, the publication is Canadian Journal of Chemistry (2015), 93(1), 98-105, database is CAplus.

Dual water and organic solvent soluble 3-aryl-3-(trifluormethyl) diazirine-functionalized gold nanoparticles (AuNPs) were prepared through a place exchange reaction from triethylene glycol monomethyl ether (EG₃-Me) capped AuNPs. These nanoparticles were fully characterized using ¹H and ¹⁹F NMR spectroscopy, TEM, TGA, and XPS. TGA along with ¹H NMR data allowed the determination of 15% incorporation of diazirine (Diaz) ligands onto mixed monolayer AuNPs, while TEM images showed an average diameter of 2.3 ± 0.5 nm. This information led to the estimated mol. formula of Au₄₀₀ (S-EG₄-Diaz)₄₀ (S-EG₃-Me)₂₃₀ for these AuNPs. It is noteworthy that high-resolution XPS was a powerful tool for quant. anal. Irradiation of the diazirine capped AuNPs resulted in nitrogen extrusion and the formation of a highly reactive carbene with evidence of a portion of the reaction proceeding via the diazo intermediate and thus requiring a 2nd photon for activation. The carbene species generated was used to tether the attached AuNPs via insertion into C=C or O-H functionality inherent on various substrates. Here, photolysis of the diazirine modified AuNPs in the presence of a variety of model carbene scavengers led to clean and efficient insertion products while maintaining their solubility in polar solvents.

Canadian Journal of Chemistry published new progress about 360-92-9. 360-92-9 belongs to amides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Amine,Aliphatic hydrocarbon chain,Amide, name is N,N-Diethyl-2,2,2-trifluoroacetamide, and the molecular formula is C6H10F3NO, HPLC of Formula: 360-92-9.

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

Sathunuru, Ramadas published the artcileFacile synthesis of 4H-naphtho[2,3-e] derivatives of 1,3-thiazines and 1,3-selenazines and naphtho[2′,3′:4,5] derivatives of selenolo[2,3-b]pyridines and thieno[2,3-b]pyridines via 2,3- didehydronaphthalene, Product Details of C5H10N2OS, the publication is ARKIVOC (Gainesville, FL, United States) (2004), 51-60, database is CAplus.

Thiaazadienes (2a–e), selenoazadienes (6a–f), Barton selenium esters (8a–e) and Barton sulfur esters (10a–e) react with 2,3-didehydronaphthalene (4) generated from (phenyl)[(3-trimethylsilyl)-2-naphthyl]iodonium triflate (3) at 0°C to give 4H-naphtho[2,3-e]-1,3-thiazines (5a–e), 4H-naphtho[2,3-e]-1,3-selenazines (7a–f), naphtho[2′,3′:4,5]selenolo[2,3-b]pyridines (9a–e) and naphtho[2′,3′:4,5]thieno[2,3-b]pyridines (11a–d). The x-ray and mol. structure of 5e and 7b are reported.

ARKIVOC (Gainesville, FL, United States) published new progress about 14294-10-1. 14294-10-1 belongs to amides-buliding-blocks, auxiliary class Morpholine,Thiourea,Amine,Amide, name is Morpholine-4-carbothioamide, and the molecular formula is C5H10N2OS, Product Details of C5H10N2OS.

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

Jing, Zhi-Fei published the artcileInhibition of miR-34a-5p can rescue disruption of the p53-DAPK axis to suppress progression of clear cell renal cell carcinoma, Quality Control of 380315-80-0, the publication is Molecular Oncology (2019), 13(10), 2079-2097, database is CAplus and MEDLINE.

DAPK, a transcriptional target of the p53 protein, has long been characterized as a tumor suppressor that acts as a neg. regulator in multiple cellular processes. However, increasing studies have suggested that the role of DAPK may vary depending on cell type and cellular context. Thus far, the expression and function of DAPK in clear cell renal cell carcinoma (ccRCC) remain ambiguous. Since ccRCC behaves in an atypical way with respect to p53, whether the p53-DAPK axis functions normally in ccRCC is also an intriguing question. Here, tissue specimens from 61 ccRCC patients were examined for DAPK expression. Functional studies regarding apoptosis, growth, and migration were used to determine the role of DAPK in renal cancer cells. The validity of the p53-DAPK axis in ccRCC was also determined Our study identified DAPK as a neg. regulator of ccRCC, and its expression was reduced in certain subgroups. However, the p53-DAPK axis was disrupted due to upregulation of miR-34a-5p under stressed conditions. miR-34a-5p was identified as a novel repressor of DAPK acting downstream of p53. Inhibition of miR-34a-5p can correct the p53-DAPK axis disruption by upregulating DAPK protein and may have potential to be used as a therapeutic target to improve outcomes for ccRCC patients.

Molecular Oncology published new progress about 380315-80-0. 380315-80-0 belongs to amides-buliding-blocks, auxiliary class Apoptosis,p53, name is N-((4-Acetamidophenyl)carbamothioyl)-4-(tert-butyl)benzamide, and the molecular formula is C20H23N3O2S, Quality Control of 380315-80-0.

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

Kamble, Sumit B. published the artcileA single pot organocatalytic diastereoselective synthesis of fluorescent ring fused 2-pyridone decalines via a domino Knoevenagel/Michael/hydro-lactamisation sequence, Formula: C5H8N2O, the publication is Organic Chemistry Frontiers (2021), 8(18), 5032-5039, database is CAplus.

Multifunctional ring fused octahydro 3-CN-2-pyridone I (R = Ph, thiophen-2-yl, 1,3-benzodioxol-5-yl, etc.; R¹ = H, Me, Et) decaline motifs are constructed by a single pot multicomponent, diastereoselective, organocatalytic domino approach. Three consecutive catalytic reaction sequences are presented, wherein L-proline plays a catalytic dual role for Knoevenagel condensation and Michael addition co-operatively with PhCOOH, followed by annulation by hydro-lactamisation. Compounds containing bromine, chlorine, methoxy and methylenedioxy groups showed aggregation-induced fluorescence under long-range UV exposure. The present method is a green synthetic strategy with the following features: high diastereoselectivity (dr > 20), catalytic activity, high yields, cost-effective nature, a simple, mild, and operationally scalable process, and broad substrate scope.

Organic Chemistry Frontiers published new progress about 15029-36-4. 15029-36-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Aliphatic hydrocarbon chain,Amide, name is 2-Cyano-N-ethylacetamide, and the molecular formula is C5H8N2O, Formula: C5H8N2O.

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

Bai, Shao-Tao published the artcileHydrogen Bond Directed ortho-Selective C-H Borylation of Secondary Aromatic Amides, Related Products of amides-buliding-blocks, the publication is Angewandte Chemie, International Edition (2019), 58(37), 13039-13043, database is CAplus and MEDLINE.

Reported is an Ir catalyst for ortho-selective C-H borylation of challenging secondary aromatic amide substrates, and the regioselectivity is controlled by H-bond interactions. The BAIPy-Ir catalyst forms three H bonds with the substrate during the crucial activation step, and allows ortho-C-H borylation with high selectivity. The catalyst displays unprecedented ortho selectivities for a wide variety of substrates that differ in electronic and steric properties, and the catalyst tolerates various functional groups. The regioselective C-H borylation catalyst is readily accessible and converts substrates on gram scale with high selectivity and conversion.

Angewandte Chemie, International Edition published new progress about 1197171-76-8. 1197171-76-8 belongs to amides-buliding-blocks, auxiliary class Boronic acid and ester,Amine,Benzene,Amide,Boronate Esters,Boronic Acids,Boronic acid and ester,, name is N-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide, and the molecular formula is C14H20BNO3, Related Products of amides-buliding-blocks.

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

Shukla, J. S. published the artcileSome newer cyanoethylated alkyl- and aryl-substituted cyanoacetamides as insecticides. Part III, Recommanded Product: 2-Cyano-N-ethylacetamide, the publication is Journal of the Indian Chemical Society (1976), 53(2), 196-7, database is CAplus.

Cyanoacetamides NCC(CH2CH2CN)2CONHR (I, R = C1-C4 alkyl, PhCH2, 2-MeC6H4, 1- or 2- naphthyl) were prepared by reaction of NCCH2CO2Et with RNH2, followed by cyanoethylation with CH2CHCN in dioxane. Insecticidal test data were given for I and several other cyanoethylated amides.

Journal of the Indian Chemical Society published new progress about 15029-36-4. 15029-36-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Aliphatic hydrocarbon chain,Amide, name is 2-Cyano-N-ethylacetamide, and the molecular formula is C13H15NO6S, Recommanded Product: 2-Cyano-N-ethylacetamide.

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