Month: January 2023

Synthesis and biological evaluation of novel hybrid compounds derived from gallic acid and the 2-aminothiophene derivatives was written by Mahdavi, Behnam;Hosseyni-Tabar, Seyed Mahmood;Rezaei-Seresht, Esmail;Rezaei-Seresht, Hasan;Falanji, Farahnaz. And the article was included in Journal of the Iranian Chemical Society in 2020.Formula: C8H8N2S This article mentions the following:

Gallic acid (GA) and its benzamide derivatives have a wide variety of biol. activities, such as antimicrobial, antioxidant, anticancer. In this study, we have reported the synthesis of some new hybrid compounds comprised of the 2-aminothiophene and GA moieties and evaluation of their cytotoxic activities against HeLa (cervical cancer), HCT116 (human colon cancer), and FT (fibroblast) cell lines as well as antimicrobial activities against some Gram-pos. and Gram-neg. bacteria. The reaction of some 2-aminothiophene derivatives (previously prepared from the Gewald reaction) with galloyl chloride having the acetylated hydroxyl groups and the subsequent deprotection of the hydroxyl groups gave the desired hybrid compounds Then, the antimicrobial activity of the compounds was evaluated using disk diffusion and min. inhibitory concentration assays. Finally, the MTT assay was carried out to evaluate the cytotoxicity of the synthesized compounds on the mentioned cell lines. The structure of the synthesized compounds was elucidated by conventional spectroscopic methods such as NMR, FT-IR, and UV-Vis spectroscopy. All compounds prevented the growth of Staphylococcus coagulase more than the pos. control of chloramphenicol, and one compound was more sensitive to the growth of Klebsiella pneumonia compared to the standard antibiotic. All compounds showed acceptable activity against cancer cells. The highest activity was observed against HeLa with an IC50 value of 3.2 μg/mL for compound 3d and against HCT116 with IC50 of 59.4 μg/mL for 3b. The high anticancer activity of compound 3d against HeLa allows us to consider it as a good lead compound for the development of new potent anticancer agents for the treatment of cervical cancer. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Formula: C8H8N2S).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. Nitriles are susceptible to hydrogenation over diverse metal catalysts. The reaction can afford either the primary amine (RCH2NH2) or the tertiary amine ((RCH2)3N), depending on conditions.Formula: C8H8N2S

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Structure-activity relationships in the formation of amides from substituted N-benzylanilines was written by Ulgen, M.;Gorrod, J. W.;Barlow, D.. And the article was included in Xenobiotica in 1994.HPLC of Formula: 10282-32-3 This article mentions the following:

The in vitro hepatic microsomal metabolism of certain substituted N-benzylanilines was studied in the male hamster to establish the mechanism(s) and process(es) involved in the formation of the corresponding amides. N-benzyl-2,4,6-trihalogeno, N-benzyl-4-cyano- and N-benzyl-4-nitroanilines were only metabolized by N-debenzylation. However, N-benzyl-4-methyl- and N-benzyl-2,4,6-trimethylanilines gave rise to both the corresponding amide and nitrone metabolites together with dealkylation products. These latter two substrates also produced hydroxymethyl metabolites as major products. Metabolism of N-(2,4,6-trimethylbenzyl)aniline also led to the formation of an amide metabolite. The dealkylation products, the corresponding imine and an unknown metabolite, probably an hydroxylated products were also detected with this substrate. N-(2,4-dichlorobenzyl) and N-(2,6-dichlorobenzyl)anilines yielded the corresponding nitrone metabolites; but no amide metabolite was detected. Oxidative dealkylation leading to the formation of the corresponding primary anilines and aldehydes, together with para hydroxylation of aniline rings, were established as major routes of metabolism for both compounds Similarly, neither N-(2,4,6-trifluorobenzyl) nor N-(4-nitrobenzyl)anilines produced any amide metabolite although dealkylation products were detected. The pattern of amide formation observed for these N-benzylsubstituted anilines is discussed in terms of the steric and electronic effects of their aromatic substituents. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3HPLC of Formula: 10282-32-3).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. HPLC of Formula: 10282-32-3

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Progress against Escherichia coli with the Oxazolidinone Class of Antibacterials: Test Case for a General Approach To Improving Whole-Cell Gram-Negative Activity was written by Takrouri, Khuloud;Cooper, Harold D.;Spaulding, Adnrew;Zucchi, Paula;Koleva, Bilyana;Cleary, Dillon C.;Tear, Westley;Beuning, Penny J.;Hirsch, Elizabeth B.;Aggen, James B.. And the article was included in ACS Infectious Diseases in 2016.Name: 2-Bromo-4-hydroxybenzonitrile This article mentions the following:

Novel antibacterials with activity against the Gram-neg. bacteria associated with nosocomial infections, including Escherichia coli and other Enterobacteriaceae, are urgently needed due to the increasing prevalence of multidrug-resistant strains. A major obstacle that has stalled progress on nearly all small-mol. classes with potential for activity against these species has been achieving sufficient whole-cell activity, a difficult challenge due to the formidable outer membrane and efflux barriers intrinsic to these species. Using a set of compound design principles derived from available information relating physicochem. properties to Gram-neg. entry or activity, we synthesized and evaluated a focused library of oxazolidinone analogs, a currently narrow spectrum class of antibacterials active only against Gram-pos. bacteria. In this series, we have explored the effectiveness for improving Gram-neg. activity by identifying and combining beneficial structural modifications in the C-ring region. We have found polar and/or charge-carrying modifications that, when combined in hybrid C-ring analogs, appear to largely overcome the efflux and/or permeability barriers, resulting in improved Gram-neg. activity. In particular, those analogs least effected by efflux and the permeation barrier had significant zwitterionic character. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-hydroxybenzonitrile (cas: 82380-17-4Name: 2-Bromo-4-hydroxybenzonitrile).

2-Bromo-4-hydroxybenzonitrile (cas: 82380-17-4) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.Name: 2-Bromo-4-hydroxybenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

3-Amino-2,1-benzisothiazole. Synthesis of some chloro and trifluoromethyl derivatives was written by Gray, J.;Waring, D. R.. And the article was included in Journal of Heterocyclic Chemistry in 1980.Product Details of 53312-77-9 This article mentions the following:

7-Chloro-, 4,7-dichloro-, 5- and 7-(trifluoromethyl), 5-chloro-6-(trifluoromethyl)- and 5-chloro-7-(trifluoromethyl)-3-amino-2,1-benzisothiazoles were prepared Preparative details are included for a number of precursors to the benzisothiazoles which have not previously been described. Visible spectra of some azo dyes prepared from the title compounds with a selected coupler are discussed with reference to substituent effects. In the experiment, the researchers used many compounds, for example, 2-Amino-3-chlorobenzonitrile (cas: 53312-77-9Product Details of 53312-77-9).

2-Amino-3-chlorobenzonitrile (cas: 53312-77-9) belongs to nitriles. The electronic structure of nitriles is very similar to that of an alkyne with the main difference being the presence of a set of lone pair electrons on the nitrogen. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Product Details of 53312-77-9

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

9-Amino-5,7-dibromo-1,2,3,4-tetrahydroacridine hemihydrate was written by Celik, Ismail;Akkurt, Mehmet;Ekiz, Makbule;Okten, Salih;Tutar, Ahmet;Ersanli, Cem Cuneyt. And the article was included in IUCrData in 2017.Safety of 2-Amino-3,5-dibromobenzonitrile This article mentions the following:

The asym. unit of the title compound, C₁₃H₁₂Br₂N₂·0.5H₂O, includes two mols. of 5,7-dibromo-1,2,3,4-tetrahydroacridin-9-amine and one water mol. In the crystal, C-H···O, N-H···N, N-H···O and O-H···N hydrogen bonds connect the mols., forming a two-dimensional network parallel to (010). The two-dimensional sheets are further assembled into a three-dimensional structure through C-H···π and π-π stacking interactions [centroid-centroid distance = 3.719 (2) Å]. In the experiment, the researchers used many compounds, for example, 2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5Safety of 2-Amino-3,5-dibromobenzonitrile).

2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. Nitriles are susceptible to hydrogenation over diverse metal catalysts. The reaction can afford either the primary amine (RCH2NH2) or the tertiary amine ((RCH2)3N), depending on conditions.Safety of 2-Amino-3,5-dibromobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Regioselective Borylation of the C-H Bonds in Alkylamines and Alkyl Ethers. Observation and Origin of High Reactivity of Primary C-H Bonds Beta to Nitrogen and Oxygen was written by Li, Qian;Liskey, Carl W.;Hartwig, John F.. And the article was included in Journal of the American Chemical Society in 2014.Formula: C12H14N2O This article mentions the following:

Borylation of aliphatic C-H bonds in alkylamines and alkyl ethers to form primary aminoalkyl and alkoxyalkyl boronate esters and studies on the origin of the regioselectivity of these reactions are reported. The products of these reactions can be used directly in Suzuki-Miyaura cross-coupling reactions or isolated as air-stable potassium trifluoroborate salts. Selective borylation of the terminal C-H bond at the positions β to oxygen and nitrogen occurs in preference to borylation of the other terminal C-H bonds. Exptl. studies and computational results show that C-H bond cleavage is the rate-determining step of the current borylation reactions. The observed higher reactivity of C-H bonds at the terminal position of ethylamines and ethers results from a combination of attractive Lewis acid-base and hydrogen-bonding interactions, as well as typical repulsive steric interactions, in the transition state. In this transition state, the heteroatom lies directly above the boron atom of one boryl ligand, creating a stabilizing interaction between the weak Lewis acid and Lewis base, and a series of C-H bonds of the substrate lie near the oxygen atoms of the boryl ligands, participating in a set of weak C-H···O interactions that lead to significant stabilization of the transition state forming the major product. In the experiment, the researchers used many compounds, for example, 4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4Formula: C12H14N2O).

4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4) belongs to nitriles. The electronic structure of nitriles is very similar to that of an alkyne with the main difference being the presence of a set of lone pair electrons on the nitrogen. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Formula: C12H14N2O

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

New Insights into the Reaction Capabilities of Ionic Organic Bases in Cu-Catalyzed Amination was written by Lo, Quintin A.;Sale, David;Braddock, D. Christopher;Davies, Robert P.. And the article was included in European Journal of Organic Chemistry in 2019.Application In Synthesis of 4-(Benzylamino)benzonitrile This article mentions the following:

The application of ionic organic bases in the copper-catalyzed amination reaction (Ullmann reaction) has been studied at rt, with sub-mol-% catalyst loadings, and with amines at elevated temperatures The cation present in the base has been shown to have little effect on the reaction at standard catalyst and ancillary ligand loadings, whereas the choice of anion is crucial for good reactivity. A substrate scope carried out at rt with the best performing bases, TBAM (bis[tetrabutylammonium]malonate) and bis(tetra-(n-butyl)phosphonium) malonate (TBPM), showed both bases to be highly effective under these mild reaction conditions. Moreover, under sub-mol % catalyst loadings and rt conditions, TBPM gave good yields for a number of different amines and aryl iodides. By using more forceful conditions (120°) moderate to excellent yields of cross-coupled products. As part of this work a study on the stability of the organic bases at 120° was undertaken. TBAM is shown to decompose to give nBu₃N and mono-butylmalonate at higher temperatures, and this can be correlated to a decrease in performance in the coupling reaction. The phosphonium cations in TBPM did not undergo analogous reactivity but were shown instead to experience some degree of deprotonation at the α-CH₂ to generate phosphonium ylides. This however did not lead to a significantly degradation in the activity of the TBPM in the cross-coupling reaction. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Application In Synthesis of 4-(Benzylamino)benzonitrile).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. Nitriles are susceptible to hydrogenation over diverse metal catalysts. The reaction can afford either the primary amine (RCH2NH2) or the tertiary amine ((RCH2)3N), depending on conditions.Application In Synthesis of 4-(Benzylamino)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Direct oxidative esterification of alcohols and hydration of nitriles catalyzed by a reusable silver nanoparticle grafted onto mesoporous polymelamine formaldehyde (AgNPs@mPMF) was written by Ghosh, Kajari;Iqubal, Asif Md.;Molla, Rostam Ali;Mishra, Ashutosh;Kamaluddin;Islam, Sk Manirul. And the article was included in Catalysis Science & Technology in 2015.Related Products of 55406-13-8 This article mentions the following:

A nitrogen-rich mesoporous organic polymer was synthesized as a novel support. A silver nanoparticle was synthesized and grafted onto it. The prepared catalyst (AgNPs@mPMF) was characterized by powder X-ray diffraction (XRD), SEM(SEM) and energy dispersive X-ray spectrometry (EDS), thermogravimetric anal. (TGA), high-resolution transmission electron microscopy (HRTEM), UV-vis diffuse reflectance spectroscopy (DRS), N₂ adsorption, Raman spectroscopy and EPR study. The catalytic activity was evaluated for the oxidative esterification reaction of alcs. and hydration of nitriles. The oxidative esterification reaction was carried out for various activated alcs. giving excellent yields of the corresponding ester products. The catalyst was also efficient in the hydration of nitriles. Both reactions were optimized by varying the bases, temperatures and solvents. The catalyst can be facilely recovered and reused six times without a significant decrease in its activity and selectivity. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Related Products of 55406-13-8).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) belongs to nitriles. Nitrile function is a very important functional group because it can be manipulated to other functional groups such as carboxylic acid by hydrolysis or amine by reduction, respectively. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.Related Products of 55406-13-8

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reaction of 4-(diethylamino)salicylaldehyde with malononitrile was written by Tkach, I. I.;Reznichenko, A. V.;Luk’yanets, E. A.. And the article was included in Khimiya Geterotsiklicheskikh Soedinenii in 1992.Name: 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile This article mentions the following:

Treating 4-(diethylamino)salicylaldehyde (I) with CH₂(CN)₂ in AcOH gave 27% coumarin derivative II and 6.2% coumarin III; in polyphosphoric acid 53% amide IV was obtained; and in Ac₂O 49% dicyanovinyl derivative V was obtained. Addnl. obtained were thione VI and benzopyranonaphthyridines VII (R = H, Et). In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Name: 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile).

7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Name: 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Nickel Catalyzed Regiodivergent Cross-Coupling Alkylation of Aryl Halides with Redox-Active Imines was written by Huang, Long;Kancherla, Rajesh;Rueping, Magnus. And the article was included in ACS Catalysis in 2022.Formula: C11H13N This article mentions the following:

Herein, a visible light nickel-catalyzed protocol for the deaminative cross-coupling of redox-active imines with various electrophiles that allow for the rapid construction of C(sp³) enriched arene Ar(t-Bu)/Me₂CH₂Ar [Ar = 4-NCC₆H₄, 4-Ph(CO)C₆H₄, 3-NCC₆H4, etc.]/AcAr [Ar = 4-((Me)₂(Et))CC₆H₄, 4-(C(O)OEtCH₂(Me)₂)CC₆H₄, 4-((PhCH₂CH₂)(Me)₂)CC₆H₄, etc.] in a regiodivergent manner. Key to the success of this protocol was the combination of a readily available organic photocatalyst and a Lewis acid additive. As an addnl. approach to alkylarenes, also showcased that the nature of electrophiles dictates the regiochem. outcome. In the experiment, the researchers used many compounds, for example, 3-(tert-Butyl)benzonitrile (cas: 154532-34-0Formula: C11H13N).

3-(tert-Butyl)benzonitrile (cas: 154532-34-0) belongs to nitriles. Nitrile compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Formula: C11H13N

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts