Month: December 2022

Surikova, O. V. published the artcileSynthesis, anthelmintic, and insecticidal activity of 2-(3-methyl-6-methoxy-7-ethoxy-3,4-dihydroisoquinol-1-yl)acetamides, Product Details of C5H8N2O, the publication is Pharmaceutical Chemistry Journal (2015), 48(10), 665-668, database is CAplus.

A series of 2-(3-methyl-6-methoxy-7-ethoxy-3,4-dihydroisoquinol-1-yl)acetamides of formula I •HCl [R¹ = NH₂, NHEt, 1-morpholino, etc.] were synthesized via cyclocondensation of O-ethylated eugenol with cyanoacetamides. Hydrochlorides of the synthesized compounds exhibited anthelmintic activity. The unsubstituted amide was the most active and exhibited activity equal to that of levamisole and significantly greater than that of pyrantel. The insecticidal activity of the synthesized compounds was inferior to that of imidacloprid.

Pharmaceutical Chemistry Journal 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 C15H14O, Product Details of C5H8N2O.

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

Spitzner, R. published the artcileKetovinylization of thiocarbamides and thioureas. On the ambidence of the thioamido function, Product Details of C5H10N2OS, the publication is Tetrahedron (1982), 38(7), 927-36, database is CAplus.

Thiocarbamides and thioureas reacted as ambident systems with β-chlorovinyl ketones to give (S)-[(Z)-ketovinyl] salts. E.g., addition reaction of PhCSNH₂ with PhCOCH:CHCl in HCO₂H/HClO₄ for 1-2 h gave 78% (Z)-PhCOCH:CHSCPh:N⁺H₂ ClO₄^–. The ketovinyl salts obtained from monoprotic thiocarbamides and thioureas underwent deprotonation to give (S)-[(Z)-ketovinyl]thioimidate esters or -isothioureas, which isomerized intramolecularly on heating. E.g., deprotonation of (Z)-4-MeOC₆H₄COCH:CHSCPh:N⁺HPh ClO₄^– gave 82% (Z)-4-MeOC₆H₄COCH:CHSCPh:NPh, which on heating in PhMe gave (E)-4-MeOC₆H₄COCH:CHSCPh:NPh. Lithiated monoprotic thiocarbonamides reacted with β-chlorovinyl ketones to give N-[(E)-ketovinyl]thiocarbonamides, whereas lithiated thioureas gave S-[(E)-ketovinyl]isothioureas, which rearranged to the N-[(E)-ketovinyl]thioureas under mild conditions. E.g., lithiation and addition reaction of PhCSNHPh with PhCOCH:CHCl gave 59% (E)-PhCOCH:CHNPhCSPh, whereas similar treatment of Me₂NC(S)NHPh gave (E)-PhCOCH:CHSC(:NPh)NMe₂, which above room temperature gave (E)-PhCOCH:CHNPhC(S)NMe₂.

Tetrahedron 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 C7H13NO2, Product Details of C5H10N2OS.

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

Van Baelen, Gitte published the artcileSynthesis of 6-methyl-6H-indolo[3,2-c]isoquinoline and 6-methyl-6H-indolo[2,3-c]isoquinoline: two new unnatural isoquinoline isomers of the cryptolepine series, Safety of (2-Pivalamidophenyl)boronic acid, the publication is Tetrahedron (2008), 64(51), 11802-11809, database is CAplus.

11H-indolo[3,2-c]isoquinoline has been synthesized in two steps starting from 4-bromoisoquinoline and 2-bromoaniline via a selective Buchwald-Hartwig reaction followed by a Pd-catalyzed intramol. direct arylation involving C(sp²)-H activation. The synthesis of 7H-indolo[2,3-c]isoquinoline was achieved by a combination of a Suzuki reaction with an intramol. nitrene insertion reaction starting from 4-bromoisoquinoline and {2-[(2,2-dimethylpropanoyl)amino]phenyl}boronic acid. Selective methylation of the tetracyclic skeletons yielded the title compounds 6-methyl-6H-indolo[3,2-c]isoquinoline and 6-methyl-6H-indolo[2,3-c]isoquinoline, which have never been described in the literature before. The antiprotozoal activity and cytotoxicity of the title compounds was tested.

Tetrahedron 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 C3H8N2S, Safety of (2-Pivalamidophenyl)boronic acid.

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

Lygina, Antonina S. published the artcileTransmembrane Domain Peptide/Peptide Nucleic Acid Hybrid as a Model of a SNARE Protein in Vesicle Fusion, Name: 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, the publication is Angewandte Chemie, International Edition (2011), 50(37), 8597-8601, S8597/1-S8597/15, database is CAplus and MEDLINE.

A novel simplified model was introduced for membrane fusion mediated by SNARE proteins. The SNARE mimetic system consisted of hybrids between the transmembrane domain/linker segments from natural membrane-bound SNARE proteins and peptide nucleic acid recognition motifs. Owing to the complementarity of the PNA bas pairs, it was possible to investigate the fusion complexes with both helixes linked on the same and opposite sides of the recognition motif. The new PNA/peptide hybrids facilitated fusion of vesicles dependent on the PNA base pair sequence and on temperature

Angewandte Chemie, International Edition 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, Name: 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.

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

Wicht, Merrill M. published the artcileCobalt Werner hosts with nicotinamides: Characterisation of mixed ligand complexes and their selectivity towards ortho xylene, Category: amides-buliding-blocks, the publication is Polyhedron (2021), 115202, database is CAplus.

Cobalt host complexes which form novel Werner structures with nicotinamides were analyzed and characterized, the formation of mixed ligand complexes by crystallization with substitution of two nicotinamide ligands was achieved and selectivity toward a xylene isomer from a mixture was elucidated. Inter- and intra-mol. hydrogen bonding interactions which formed amide dimers, ring structures, discrete bonds and chains were described. In some cases, the packing was stabilized by π···π interactions between the aromatic rings of the nicotinamides. Three mixed ligand crystal structures were formed when two nicotinamide ligands in host complexes were replaced with two DMSO mols. or two methanol mols. via oxygen bridging. This formation required an understanding of the strength of interaction between the ligand and the metal ion. The investigation of pK_a, the dipole moment and electronegativity values for the interacting elements clarified the substitution process. A mixed ligand Werner clathrate [Co(NCS)₂(isonic)₂(C₂H₆OS)₂]·2(ortho-C₈H₁₀), showing characteristics both of a mixed ligand structure and a clathrate, presented a preference towards ortho-xylene from a 50:50 mixture of ortho/meta-xylenes. The single crystal structure, its thermal behavior and the Hirshfeld surfaces were used for confirmation of this finding. This study of cobalt Werner complexes with nicotinamides has explored mixed ligand complexes and the property of discrimination towards a xylene isomer from a mixture of two different isomers.

Polyhedron published new progress about 1453-82-3. 1453-82-3 belongs to amides-buliding-blocks, auxiliary class Pyridine,Amine,Amide, name is Isonicotinamide, and the molecular formula is C7H8BClO2, Category: amides-buliding-blocks.

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

Wang, Zi-Qiang published the artcileElectrochemical Synthesis of 3,5-Disubstituted-1,2,4-thiadiazoles through NH₄I-Mediated Dimerization of Thioamides, Product Details of C8H9NOS, the publication is Advanced Synthesis & Catalysis (2018), 360(21), 4043-4048, database is CAplus.

A electrochem. method for the synthesis of 3,5-disubstituted-1,2,4-thiadiazoles through NH₄I-mediated dimerization of thioamides is reported. Using the inexpensive NH₄I as electrolyte and catalyst, this electrosynthesis approach requires no oxidizing agents and enables the convenient production of diverse 1,2,4-thiadiazole products. The approach is an example of S-N bond construction through the electrochem. method.

Advanced Synthesis & Catalysis 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 C16H14O6, Product Details of C8H9NOS.

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

Gao, Shenghua published the artcileIdentification, characterization and quantification of process-related and degradation impurities in lisdexamfetamine dimesylate: identifiction of two new compounds, Category: amides-buliding-blocks, the publication is Molecules (2018), 23(12), 3125/1-3125/16, database is CAplus and MEDLINE.

Twelve impurities (process-related and degradation) in lisdexamfetamine dimesylate (LDX), a central nervous system (CNS) stimulant drug, were first separated and quantified by high-performance liquid chromatog. (HPLC) and then identified by liquid chromatog. mass spectrometry (LC-MS). The structures of the twelve impurities were further confirmed and characterized by IR, HRMS and NMR analyses. Based on the characterization data, two previously unknown impurities formed during the process development and forced degradation were proposed to be (2S)-2,6-di-(lysyl)-amino-N-[(1S)-1-methyl-2-Ph ethyl]hexanamide (Imp-H) and (2S)-2,6-diamino-N-[(1S)-1-methyl-2-(2-hydroxyphenyl)ethyl] hexanamide (Imp-M). Furthermore, these two compounds are new. Probable mechanisms for the formation of the twelve impurities were discussed based on the synthesis route of LDX. Superior separation was achieved on a YMC-Pack ODS-AQ S5 120A silica column (250 × 4.6 mm × 5 μm) using a gradient of a mixture of acetonitrile and 0.1% aqueous methanesulfonic acid solution The HPLC method was optimized in order to sep., selectively detect, and quantify all the impurities. The full identification and characterization of these impurities should prove useful for quality control in the manufacture of lisdexamfetamine dimesylate.

Molecules published new progress about 2418-95-3. 2418-95-3 belongs to amides-buliding-blocks, auxiliary class Chiral,Carboxylic acid,Amine,Aliphatic hydrocarbon chain,Ester,Amino acide derivatives, name is H-Lys(Boc)-OH, and the molecular formula is C11H22N2O4, Category: amides-buliding-blocks.

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

Ahmed, Ahmed A. M. published the artcileNew bis(pyrazolo[3,4-b]pyridines) and bis(thieno[2,3-b]pyridines) as potential acetylcholinesterase inhibitors: synthesis, in vitro and SwissADME prediction study, Category: amides-buliding-blocks, the publication is Journal of the Iranian Chemical Society, database is CAplus.

The bis(pyridine-2(1H)-thione) was prepared and taken as a key synthon of this study. The target bis(pyrazolo[3,4-b]pyridines) was prepared in good yields, by the reaction of bis(pyridine-2(1H)-thione) with appropriate hydrazonyl chlorides to yield bis(hydrazonothioates) followed by their heating in ethanolic sodium ethoxide solution Addnl., bis(pyridine-2(1H)-thione) reacted with different α-halogenated reagents to afford a new series of bis(thieno[2,3-b]pyridines), in good to excellent yields. In general, the tested series of bis(thieno[2,3-b]pyridines) demonstrated greater acetylcholinesterase inhibitory activity as well as DPPH antioxidant activity than the other series of (pyrazolo[3,4-b]pyridines). At a concentration of 100 μM, bis(thieno[2,3-b]pyridine-2-carbonitrile) showed the best acetylcholinesterase inhibitory activity with inhibition percentage of 83.2. In addition, the previous hybrid had the highest DPPH antioxidant activity, with an inhibition percentage of 82.6 when tested at a concentration of 25 μg/mL. Furthermore, SwissADME was used to predict the physicochem. properties, lipophilicity, and drug likeness of the new products.

Journal of the Iranian Chemical Society 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 C2H4ClNO, Category: amides-buliding-blocks.

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

Ahmed, Ahmed A. M. published the artcileNew piperazine-based bis(thieno[2,3-b]pyridine) and bis(pyrazolo[3,4-b]pyridine) hybrids linked to benzofuran units: Synthesis and in vitro screening of potential acetylcholinesterase inhibitors, Related Products of amides-buliding-blocks, the publication is Synthetic Communications (2022), 52(6), 912-925, database is CAplus.

Two series of piperazine-based bis(thieno[2,3-b]pyridines) I (Y = CN, COMe, CONH₂, COOEt, COPh) and bis(pyrazolo[3,4-b]pyridines) II (Z = H, Me, OMe, Cl, COOEt) were prepared in good yields, utilizing the appropriate bis(pyridinethione). The first series was obtained by reacting the previous synthon with different α-halogenated reagents, whereas the second series was produced by reacting the synthon with various hydrazonyl chlorides, and then cyclizing the resulting bis(hydrazonothioates). At 50 and 100μM concentrations, the two series were screened as potential acetylcholinesterase inhibitors. The reference donepezil had inhibition percentages of 90.7 and 93.5 at the tested concentrations Generally, bis(thieno[2,3-b]pyridine) series was found to be more effective than the other series of bis(pyrazolo[3,4-b]pyridine). Bis(thieno[2,3-b]pyridine-2-carbonitrile) inhibited acetylcholinesterase the best, with inhibition percentages of 55.2 and 88.4 at 50 and 100μM concentrations, resp. Furthermore, when tested at a concentration of 25μg/mL, the prior hybrid demonstrated the best DPPH antioxidant activity, with an inhibition percentage of 81.5 when compared to the reference ascorbic acid (inhibition percentage of 88.7).

Synthetic Communications 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 C2H4ClNO, Related Products of amides-buliding-blocks.

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

Coeck, Robin published the artcileGold and Silver-Catalyzed Reductive Amination of Aromatic Carboxylic Acids to Benzylic Amines, Safety of Isonicotinamide, the publication is ACS Catalysis (2021), 11(13), 7672-7684, database is CAplus.

The reductive amination of benzoic acid and its derivatives was an effective addition to current synthesis methods for benzylamine. However, with current technol. it was very difficult to keep the aromaticity intact when starting from benzoic acid, and salt wastes were often generated in the process. Here, a heterogeneous catalytic system for such a reductive amination, requiring solely H₂ and NH₃ as the reactants was reported. The Ag/TiO₂ or Au/TiO₂ catalysts can be used multiple times, and very little noble metal was required, only 0.025 mol % Au. The catalysts were bifunctional: the support catalyzes the dehydration of both the ammonium carboxylate to the amide and of the amide to the nitrile, while the sites at the metal-support interface promote the hydrogenation of the in situ generated nitrile. Yields of up to 92% benzylamine were obtained.

ACS Catalysis published new progress about 1453-82-3. 1453-82-3 belongs to amides-buliding-blocks, auxiliary class Pyridine,Amine,Amide, name is Isonicotinamide, and the molecular formula is C6H6N2O, Safety of Isonicotinamide.

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