Tag: M.W=150-200

Canonica, Luigi published the artcileSynthetic analeptics. I. Hydroxybenzoic acid diethylamides, Category: amides-buliding-blocks, the publication is Annali di Chimica (Rome, Italy) (1955), 205-15, database is CAplus.

Of the dialkylamides studied, the best analeptic activity was present in the diethylamides of vanillic acid. Analogs prepared and studied for pharmacol activity were the following benzoic acid diethylamides (substituent given): 4-acetoxy, m. 80-1°; 3-methoxy, b_1.7 132-4°; 2-hydroxy-4-methoxy, m. 121-2°; 2,4-dimethoxy; 2-hydroxy-5-methoxy, m. 103-4°; 3-chloro-4-hydroxy (I); 3-bromo-4-hydroxy (II), m. 158-9°; 3-nitro-4-hydroxy, m. 123-4° (decomposition); 3-chloro-4-acetoxy, m. 89° (crystallized from dilute MeOH); 3-hydroxy, m. 83°; 2-acetoxy, b₁₀ 178-80°; 2-hyhydroxy, m. 104-5°; 3-methoxy-4-hydroxy (III); 3-methoxy-4-acetoxy (IV); 3-ethoxy-4-hydroxy (V), m. 92-3°; 3-ethoxy-4-acetoxy (VI); 4-hydroxy, m. 121.5°; 4-methoxy, m. 42°; 2-acetoxy-4-methoxy, m. 120-1°; 3-bromo-4-acetoxy, m. 94-5° (crystallized from C₆H₆-petr. ether); 3,4,5-trimethoxy, m. 54°, b₅ 203-4°. Piperonylic acid diethylamide, m. 64-5° (from H₂O), and isonicotinic acid diethylamide, b₁₅ 162-4°, were also prepared In general, the acids were converted to acid chlorides with PCl₅ in CS₂ and then to the diethylamide with Et₂NH in C₆H₆. Analeptic activity is given relative to cyclopentamethylenetetrazole. Most active compounds were I to VI in decreasing consecutive order. The presence of a single OH group or OAc increased activity but not significantly. Compounds with a 3-OR group where R = Me or Et were highly active.

Annali di Chimica (Rome, Italy) published new progress about 530-40-5. 530-40-5 belongs to amides-buliding-blocks, auxiliary class Pyridine,Amine,Amide, name is N,N-Diethylisonicotinamide, and the molecular formula is C10H14N2O, Category: amides-buliding-blocks.

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

Meresaar, Urve published the artcileHydrolysis of amides. Alkaline and general acid catalyzed alkaline hydrolysis of some substituted acetamides and benzamides, Recommanded Product: N,N-Diethyl-2,2,2-trifluoroacetamide, the publication is Acta Chemica Scandinavica, Series A: Physical and Inorganic Chemistry (1974), 28(7), 715-22, database is CAplus.

AcNH2, trifluoro- and trichloroacetamide, trimethyl- and triethylammonioacetamide cation, benzamide, 4-nitrobenzamide, and N,N-diethyl-, N-cyclohexyl-, and N-benzyltrifluoroacetamide were hydrolyzed at 25 or 45° in alk. solution at ionic strength 1. The pH-rate profiles show that the rate at high pH values is more than first-order in OH- for the trialkylammonioacetamide cations, the benzamides, and N-benzyltrifluoroacetamide, which can be interpreted as OH–catalyzed breakdown of a substrate-OH- intermediate. In accord with a mechanism involving acid catalyzed breakdown of this intermediate to products, the rate of hydrolysis of these amides and of N,N-diethyltrifluoroacetamide and N-cyclohexyltrifluoroacetamide is enhanced by the presence of H phosphate or H carbonate ions. This makes it possible to determine the rate constants for the formation of the tetrahedral intermediates (k1), and the ratios of the rate constants for the uncatalyzed breakdown of the intermediates to products and for their reversion to reactants (k2/k-1). The k2/k-1 values are largely independent of electronic effects in the acyclic part but depend on such effects from substituents in the amine part. The corresponding parameters (k3/k-1) for the OH–catalyzed breakdown of the intermediates were also determined

Acta Chemica Scandinavica, Series A: Physical and Inorganic 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, Recommanded Product: N,N-Diethyl-2,2,2-trifluoroacetamide.

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

Anthony, Nahoum G. published the artcileAntimicrobial Lexitropsins Containing Amide, Amidine, and Alkene Linking Groups, Synthetic Route of 64559-06-4, the publication is Journal of Medicinal Chemistry (2007), 50(24), 6116-6125, database is CAplus and MEDLINE.

The synthesis and properties of 80 short minor groove binders, such as I, related to distamycin and the thiazotropsins were described. The design of the compounds was principally predicated upon increased affinity arising from hydrophobic interactions between minor groove binders and DNA. The introduction of hydrophobic aromatic head groups, including quinolyl and benzoyl derivatives, and of alkenes as linkers led to several strongly active antibacterial compounds with MIC for Staphylococcus aureus, both methicillin-sensitive and -resistant strains, in the range of 0.1-5 μg mL^-1, which is comparable to many established antibacterial agents. Antifungal activity was also found in the range of 20-50 μg mL^-1 MIC against Aspergillus niger and Candida albicans, again comparable with established antifungal drugs. A quinoline derivative was found to protect mice against S. Aureus infection for a period of up to six days after a single i.p. dose of 40 mg kg^-1.

Journal of Medicinal Chemistry published new progress about 64559-06-4. 64559-06-4 belongs to amides-buliding-blocks, auxiliary class Amine,Benzene,Amide,Ether, name is 3-Methoxybenzothioamide, and the molecular formula is C8H9NOS, Synthetic Route of 64559-06-4.

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

Delaine, Tamara published the artcileSynthesis of the Isonicotinoylnicotinamide Scaffolds of the Naturally Occurring Isoniazid-NAD(P) Adducts, Category: amides-buliding-blocks, the publication is Journal of Organic Chemistry (2007), 72(2), 675-678, database is CAplus and MEDLINE.

The first syntheses of the 1-hydroxy-1-(pyridin-4-yl)-1,2-dihydro-3H-pyrrolo[3,4-c]pyridin-3-one and the 3-aminocarbonyl-4-isonicotinoyl-1,4-dihydropyridine frameworks present in the isoniazid-NAD(P) adducts are described.

Journal of Organic Chemistry published new progress about 100377-32-0. 100377-32-0 belongs to amides-buliding-blocks, auxiliary class Pyridine,Amine,Amide, name is N-Methoxy-N-methylisonicotinamide, and the molecular formula is C8H10N2O2, Category: amides-buliding-blocks.

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

Epsztajn, Jan published the artcileApplication of organolithium and related reagents in synthesis. Part I. Reactions of the N,N-dialkylpyridylcarboxylic amides with lithium amides. Regioselective lithiation of N,N-diisopropylpyridylcarboxylic amides, a useful method for synthesis of 2,3- and 3,4-disubstituted pyridines, Name: N,N-Diethylisonicotinamide, the publication is Tetrahedron Letters (1980), 21(49), 4739-42, database is CAplus.

The reactions of N,N-dialkylpyridyl carboxamides I (R = Me, Et, CHMe₂) with Et₂NLi and (Me₂CH)₂NLi were examined Lithiation of I (R = CHMe₂) was regioselective, providing a convenient route to 2,3- and 3,4-disubstituted pyridines. E.g., I (R = CHMe₂, CONR₂ group in 2-position) was regioselectively lithiated by (Me₂CH)₂NLi (Et₂O, -78°, 2 h) to give II (R = Li), which reacted with DMF to give 35% of aldehyde I (R = CHO). The aldehyde reacted with CH₂(CO₂H)₂ in the Doebner modification of the Knoevenagel reaction to give 29% of I (R = CH:CHCO₂H). The lithio derivative II (R = Li) reacted with Ph₂CO to give 81% I (R = CPh₂OH).

Tetrahedron Letters published new progress about 530-40-5. 530-40-5 belongs to amides-buliding-blocks, auxiliary class Pyridine,Amine,Amide, name is N,N-Diethylisonicotinamide, and the molecular formula is C10H14N2O, Name: N,N-Diethylisonicotinamide.

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

Remen, Lubos published the artcilePreparation, Antiepileptic Activity, and Cardiovascular Safety of Dihydropyrazoles as Brain-Penetrant T-Type Calcium Channel Blockers, Category: amides-buliding-blocks, the publication is Journal of Medicinal Chemistry (2016), 59(18), 8398-8411, database is CAplus and MEDLINE.

Aryldihydropyrazolecarboxamides such as I were prepared as brain-penetrating T-type calcium channel blockers for potential use as antiepileptic agents; their inhibition of T-type calcium channels over related calcium channels responsible for potential cardiovascular side effects was determined I was advanced to in vivo studies, where it demonstrated efficacy in the WAG/Rij rat model of generalized nonconvulsive, absence-like epilepsy. I was not efficacious in the basolateral amygdala kindling rat model of temporal lobe epilepsy, and it led to prolongation of the PR interval in ECG recordings in rodents.

Journal of Medicinal Chemistry published new progress about 100377-32-0. 100377-32-0 belongs to amides-buliding-blocks, auxiliary class Pyridine,Amine,Amide, name is N-Methoxy-N-methylisonicotinamide, and the molecular formula is C8H10N2O2, Category: amides-buliding-blocks.

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

Ghosh, Arghya published the artcileNHC-Catalyzed [3 + 3] Annulation of Thioamides and Modified Enals for the Enantioselective Synthesis of Functionalized Thiazinones, Synthetic Route of 64559-06-4, the publication is Organic Letters (2019), 21(21), 8598-8602, database is CAplus and MEDLINE.

N-Heterocyclic carbene (NHC)-catalyzed [3 + 3] annulation of thioamides with modified enals allowing the enantioselective synthesis of functionalized 1,3-thiazin-4-ones is reported. The NHC generated from the chiral triazolium salt was optimal and the reaction is initiated by the thia-Michael addition to catalytically generated α,β-unsaturated acylazolium intermediates derived from 2-bromoenals, followed by intramol. cyclization. This operationally simple procedure offers a straightforward and rapid access to target compounds in moderate to good yields and enantiomeric ratio values.

Organic Letters published new progress about 64559-06-4. 64559-06-4 belongs to amides-buliding-blocks, auxiliary class Amine,Benzene,Amide,Ether, name is 3-Methoxybenzothioamide, and the molecular formula is C8H9NOS, Synthetic Route of 64559-06-4.

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

Favalli, Nicholas published the artcileLarge screening of DNA-compatible reaction conditions for Suzuki and Sonogashira cross-coupling reactions and for reverse amide bond formation, Related Products of amides-buliding-blocks, the publication is Bioorganic & Medicinal Chemistry (2021), 116206, database is CAplus and MEDLINE.

Progress in DNA-encoded chem. library synthesis and screening crucially relies on the availability of DNA-compatible reactions, which proceed with high yields and excellent purity for a large number of possible building blocks. In the past, exptl. conditions have been presented for the execution of Suzuki and Sonogashira cross-coupling reactions on-DNA. In this article, our aim was to optimize Suzuki and Sonogashira reactions, comparing our results to previously published procedures. We have tested the performance of improved conditions using 606 building blocks (including boronic acids, pinacol boranes and terminal alkynes), achieving >70% conversion for 84% of the tested mols. Moreover, we describe efficient exptl. conditions for the on-DNA synthesis of amide bonds, starting from DNA derivatives carrying a carboxylic acid moiety and 300 primary, secondary and aromatic amines, as amide bonds are frequently found in DNA-encoded chem. libraries thanks to their excellent DNA compatibility.

Bioorganic & Medicinal Chemistry published new progress about 849833-86-9. 849833-86-9 belongs to amides-buliding-blocks, auxiliary class Fluoride,Boronic acid and ester,Amine,Benzene,Amide,Boronic Acids,Boronic Acids,Boronic acid and ester, name is (3-Fluoro-4-(methylcarbamoyl)phenyl)boronic acid, and the molecular formula is C8H9BFNO3, Related Products of amides-buliding-blocks.

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

Dub, Pavel A. published the artcileEngineering Catalysts for Selective Ester Hydrogenation, Recommanded Product: N,N-Diethyl-2,2,2-trifluoroacetamide, the publication is Organic Process Research & Development (2020), 24(3), 415-442, database is CAplus.

The development of efficient catalysts and processes for synthesizing functionalized (olefinic and/or chiral) primary alcs. and fluoral hemiacetals is currently needed. These are valuable building blocks for pharmaceuticals, agrochems., perfumes, and so forth. From an economic standpoint, bench-stable Takasago Int. Corp.’s Ru-PNP, more commonly known as Ru-MACHO, and Gusev’s Ru-SNS complexes are arguably the most appealing mol. catalysts to access primary alcs. from esters and H₂ (Waser, M. et al. Organic Proc. Res. Dev. 2018,22, 862). This work introduces economically competitive Ru-SNP(O)_z complexes (z = 0, 1), which combine key structural elements of both of these catalysts. In particular, the incorporation of SNP heteroatoms into the ligand skeleton is crucial for the design of a more product-selective catalyst in the synthesis of fluoral hemiacetals under kinetically controlled conditions. Based on exptl. observations and computational anal., this paper further extends the current state-of-the-art understanding of the accelerative role of KO-t-Bu in ester hydrogenation. It attempts to explain why a maximum turnover occurs starting at ∼25 mol % base, in contrast to only ∼10 mol % with ketones as substrates.

Organic Process Research & Development 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, Recommanded Product: N,N-Diethyl-2,2,2-trifluoroacetamide.

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