Author: Jessica.F

Design, synthesis, AChE/BChE inhibitory activity, and molecular docking of spiro[chromeno[4,3-b]thieno[3,2-e]pyridine]-7-amine tacrine hybrids was written by Kappenberg, Yuri G.;Nogara, Pablo A.;Stefanello, Felipe S.;Moretto, Luis Henrique;Santos, Patricia M.;Rocha, Joao. B. T.;Zanatta, Nilo;Martins, Marcos. A. P.;Bonacorso, Helio G.. And the article was included in Journal of Molecular Structure in 2022.Synthetic Route of C8H8N2S This article mentions the following:

A new series of 12 examples of spiro[chromeno[4,3-b]thieno[3,2-e]pyridine]-7-amines tacrine hybrids were designed and synthesized as cholinesterase inhibitors. These new compounds were synthesized at 20-33% yields by a one-pot two-step cyclocondensation reaction of 2-aminothiophene-3-carbonitriles with spiro[chroman-2,10-cycloalkan]-4-ones using AlCl₃ as the catalyst without solvent and under conventional thermal heating. Subsequently, these new tacrine hybrids were subjected to AChE and BChE inhibitory activity evaluation and mol. docking studies. In vitro cholinesterase assays and in silico docking indicated that all new tacrine analgs were not AChE inhibitors. However, the mols. without a carbocyclic moiety geminated to the thiophene ring, i.e., spiro scaffolds that originated from cyclopentanone , cyclohexanone , and cycloheptanone showed the highest inhibitory potency against the BChE enzyme, thereby proving to be promising candidates for evaluation in Alzheimer’s disease synthetic models. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Synthetic Route of 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. Industrially, the main methods for producing nitriles are ammoxidation and hydrocyanation. Both routes are green in the sense that they do not generate stoichiometric amounts of salts.Synthetic Route of C8H8N2S

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Substrate profiling of the cobalt nitrile hydratase from Rhodococcus rhodochrous ATCC BAA 870 was written by Mashweu, Adelaide R.;Chhiba-Govindjee, Varsha P.;Bode, Moira L.;Brady, Dean. And the article was included in Molecules in 2020.Reference of 1753-48-6 This article mentions the following:

The aromatic substrate profile of the cobalt nitrile hydratase from Rhodococcus rhodochrous ATCC BAA 870 was evaluated against a wide range of nitrile containing compounds (>60). To determine the substrate limits of this enzyme, compounds ranging in size from small (90 Da) to large (325 Da) were evaluated. Larger compounds included those with a bi-aryl axis, prepared by the Suzuki coupling reaction, Morita-Baylis-Hillman adducts, heteroatom-linked diarylpyridines prepared by Buchwald-Hartwig cross-coupling reactions and imidazo[1,2-a]pyridines prepared by the Groebke-Blackburn-Bienayme multicomponent reaction. The enzyme active site was moderately accommodating, accepting almost all of the small aromatic nitriles, the diarylpyridines and most of the bi-aryl compounds and Morita-Baylis-Hillman products but not the Groebke-Blackburn-Bienayme products. Nitrile conversion was influenced by steric hindrance around the cyano group, the presence of electron donating groups (e.g., methoxy) on the aromatic ring, and the overall size of the compound In the experiment, the researchers used many compounds, for example, 2-Aminopyrimidine-5-carbonitrile (cas: 1753-48-6Reference of 1753-48-6).

2-Aminopyrimidine-5-carbonitrile (cas: 1753-48-6) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Reference of 1753-48-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Chemically Robust and Bifunctional Co(II)-Framework for Trace Detection of Assorted Organo-toxins and Highly Cooperative Deacetalization-Knoevenagel Condensation with Pore-Fitting-Induced Size-Selectivity was written by Seal, Nilanjan;Palakkal, Athulya S.;Singh, Manpreet;Goswami, Ranadip;Pillai, Renjith S.;Neogi, Subhadip. And the article was included in ACS Applied Materials & Interfaces in 2021.Synthetic Route of C18H10N2 This article mentions the following:

Acute detection of assorted classes of organo-toxins in a practical environment is an important sustainable agenda, whereas cooperative and recyclable catalysis can mitigate hazards by minimizing energy requirements and reducing waste generation. The authors constructed an acid-/base-stable Co(II)-framework with a network topol., (Me)₂NH₂·[Co₃(L)₂(_μ2-OH)(bpy)_1.5(H₂O)₃] (bpy = 4,4′-bipyridine, H₃L = 4,4′,4”-tricarboxytriphenylamine) with unidirectional porous channels decorated by anionic [Co₂(μ₂-OH)(COO)₄(H₂O)₃] secondary building units and neutral [CoN₂(COO)₂] nodes. Intense luminescent of the hydrolytically robust framework is harnessed for selective, fast-responsive, and regenerable detection of two detrimental organo-aromatics, 4-aminophenol (4-AP) and 2,4,6-trinitrophenol (TNP). Alongside remarkable quenching, their nanomolar detection limits (4-AP: 99.5 nM; TNP: 67.2 nM) rank among the lowest reported values in H₂O and corroborate their ultra-sensitivity. D. functional theory (DFT) calculations verify the electron-transfer route of sensing through portraying redistribution of energy levels of MOs in a three-dimensional network by each analyte and further envisages noncovalent host-guest interactions. Benefiting from the concurrent existence of an open-metal site and a triphenylamine-moiety-functionalized ligand, the activated framework acts as an outstandingly cooperative heterogeneous catalyst in deacetalization-Knoevenagel condensation under mild conditions. The acid-base dual catalysis is detailed for the 1st time from combined inputs of control experiments and DFT validations. To the best of tandem reaction, larger-sized substrate exhibits insignificant conversion, and certifies rarest pore-fitting induced size-selectivity. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Synthetic Route of C18H10N2).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) 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.Synthetic Route of C18H10N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Challenging nickel-catalysed amine arylations enabled by tailored ancillary ligand design was written by Lavoie, Christopher M.;MacQueen, Preston M.;Rotta-Loria, Nicolas L.;Sawatzky, Ryan S.;Borzenko, Andrey;Chisholm, Alicia J.;Hargreaves, Breanna K. V.;McDonald, Robert;Ferguson, Michael J.;Stradiotto, Mark. And the article was included in Nature Communications in 2016.HPLC of Formula: 60710-80-7 This article mentions the following:

An operationally simple and air-stable ligand/nickel(II) pre-catalyst that accommodated the broadest combination of C(sp²)-N coupling partners reported to date for any single nickel catalyst, without the need for a precious-metal co-catalyst was reported. Key to the unprecedented performance of this pre-catalyst was the application of the new, sterically demanding yet electron-poor bisphosphine PAd-DalPhos. Featured were the first reports of nickel-catalyzed room temperature reactions involving challenging primary alkylamine and ammonia reaction partners employing an unprecedented scope of electrophiles, including transformations involving sought-after (hetero)aryl mesylates for which no capable catalyst system was known. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methylbenzonitrile (cas: 60710-80-7HPLC of Formula: 60710-80-7).

3-Amino-4-methylbenzonitrile (cas: 60710-80-7) 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. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.HPLC of Formula: 60710-80-7

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Tetrahydro-ar-1-(and 2)-naphthoic acids and their derivatives was written by Sergievskaya, S. I.;Nikhamkina, E. G.. And the article was included in Zhurnal Obshchei Khimii in 1945.Name: 5,6,7,8-Tetrahydronaphthalene-1-carbonitrile This article mentions the following:

ar-1-Aminotetralin (45 g.), 75 cc. concentrated HCl, and 200 cc. water were mixed and treated with sufficient water to dissolve the HCl salt; diazotization by 22.5 g. NaNO₂ in 300 cc. water at -5°, followed by addition to 56 g. NaCN in 500 cc. water, 80 cc. 10% NH₄OH, and 33 g. CuCl, stirring for 2-3 hrs., and steam distillation gave 5,6,7,8-tetrahydro-1-naphthonitrile (35.7%), b₅ 130-1°, b₁₇ 156-7°. Heating 15.7 g. of above with 19.8 g. NaOH, 75 cc. EtOH, and 5 cc. water at reflux gave 13 g. of the corresponding acid (I), m. 139-40° (after crystallization, m. 150-1°; solvent not given) and 0.5 g. amide (no m.p.); the hydrolysis may be conducted in a sealed tube at 140° for 8 hrs., using concentrated HCl, although the yield is lowered (ca. 50%); the same acid was obtained after alc. KOH hydrolysis of the hydrogenation product of Et 1-naphthoate. I (5 g.), 17 cc. absolute EtOH, and 1.5 cc. concentrated H₂SO₄, heated 6 hrs., yielded the Et ester, b₄128-9°; hydrogenation of Et 1-naphthoate in EtOH, using Raney Ni at 130° and 50 atm., gave the same ester, b₁₈ 165-70°. Chloride of I, obtained by heating 12 g. I with 100 g. SOCl₂, b₃ 122-3°. Treatment of this with NH₄OH gave the amide, m. 181-2° (from EtOH). The chloride (1.8 g.) in dry benzene and 2 g. Et₂NCH₂CH₂OH were refluxed for 2 hrs., and after the usual treatment, treated with Et₂O-HCl to give 2-diethylaminoethyl 5,6,7,8-tetrahydro-1-naphthoate-HCl, m. 161-2° (from benzene). Similar procedures were used in the preparation of 5,6,7,8-tetrahydro-2-naphthonitrile (from ar-2-aminotetralin), b₄ 103-4° (36%); acid, m. 153° (from EtOH) (96%); Et ester, b₄ 135.5°, b₈ 147°; chloride, b₃ 115-16°; amide, m. 140-1° (from EtOH); 2-diethylaminoethyl ester-HCl, m. 152-3° (from benzene). The alkylamino esters are weak anesthetics. In the experiment, the researchers used many compounds, for example, 5,6,7,8-Tetrahydronaphthalene-1-carbonitrile (cas: 29809-13-0Name: 5,6,7,8-Tetrahydronaphthalene-1-carbonitrile).

5,6,7,8-Tetrahydronaphthalene-1-carbonitrile (cas: 29809-13-0) 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.Name: 5,6,7,8-Tetrahydronaphthalene-1-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis and biological evaluation of novel dihydro-aryl/alkylsulfanyl-cyclohexylmethyl-oxopyrimidines (S-DACOs) as high active anti-HIV agents was written by He, Yan-Ping;Long, Jin;Zhang, Shui-Shuan;Li, Cong;Lai, Christopher Cong;Zhang, Chun-Sheng;Li, Da-Xiong;Zhang, De-Hua;Wang, Hua;Cai, Qing-Qing;Zheng, Yong-Tang. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2011.Recommanded Product: 2-Cyclohexylacetonitrile This article mentions the following:

A novel dihydro-aryl/alkylsulfanyl-cyclohexylmethyl-oxopyrimidines (S-DACOs), e.g., I, combinatory library was synthesized and evaluated with C8166 cells infected by the HIV-1_IIIB in vitro, using Nevirapine (NVP) and Zidovudine (AZT) as pos. control. The anti-HIV screening results revealed that C-6-cyclohexylmethyl substituted pyrimidinones possessed higher selective index than its 6-arylmethyl counterparts. Some compounds showed potent anti-HIV activities with EC₅₀ values of 0.012 to 0.162 nM. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Recommanded Product: 2-Cyclohexylacetonitrile).

2-Cyclohexylacetonitrile (cas: 4435-14-7) 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. 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. Recommanded Product: 2-Cyclohexylacetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

An NMR investigation of ground-state polarization of some substituted aromatic systems was written by Collins, Michael J.;Hatton, Paul M.;Sternhell, Sever. And the article was included in Australian Journal of Chemistry in 1992.Recommanded Product: 5-Methyl-2-nitrobenzonitrile This article mentions the following:

A previously established NMR method for estimating mobile bond orders was used to examine the ground-state polarization of benzene or heteroaromatic derivatives with ortho or para pairs of +R/-R substituents in benzene, naphthalene, furan, thiophene, pyrrole, quinoline, and pyrazole systems. Evidence for significant ground-state polarization which is solvent-independent was observed in these systems, especially benzene, pyrrole, and pyrazole. In the experiment, the researchers used many compounds, for example, 5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6Recommanded Product: 5-Methyl-2-nitrobenzonitrile).

5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6) 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Recommanded Product: 5-Methyl-2-nitrobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

multifunctional use of heterogeneous catalyst from littered Tectona grandis leaves towards sustainable biodiesel and chemical production was written by Gohain, Minakshi;Laskar, Khairujjaman;Phukon, Hridoyjit;Bora, Utpal;Kalita, Dipul;Deka, Dhanapati. And the article was included in Waste Management (Oxford, United Kingdom) in 2020.Recommanded Product: 55490-87-4 This article mentions the following:

Waste biomass derived heterogeneous catalyst is an excellent alternative to chem. synthesized catalysts. In this work, calcined Tectona grandis leaves were proposed as an eco-friendly, renewable and low cost heterogeneous base catalyst. The prepared catalyst was examined by FTIR, XRD, XPS, SEM, EDX, TEM, TGA, BET and Hammett indicator test. The catalyst has an appealing nature towards various chem. transformations due to its basic surface sites provided by alkali and alk. earth metals. The efficiency of the catalyst was successfully investigated by its application in biodiesel production The products were confirmed by ¹H and ¹³C NMR. 100% FAME conversion was attained using a catalyst loading of 2.5 wt% under optimized reaction parameters. The catalyst was further explored for Knoevenagel condensation reaction, in which it showed its effectiveness and recyclability towards the formation of benzylidenemalononitrile derivatives of aryl aldehydes. Thus, it is a potential ‘green catalyst’ derived from waste biomass without any addition of chems. that can replace the industrial base catalysts used for biodiesel production and Knoevenagel reaction and makes the protocol environmentally benign. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Recommanded Product: 55490-87-4).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) 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.Recommanded Product: 55490-87-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Asymmetric transfer hydrogenation of ketones catalyzed by rhenium complexes with chiral ferrocenylphosphane ligands was written by Mejia, Esteban;Aardoom, Raphael;Togni, Antonio. And the article was included in European Journal of Inorganic Chemistry in 2012.Electric Literature of C9H9NO This article mentions the following:

A series of new rhenium complexes containing chiral ferrocenyldiphosphine ligands, I (R = Ph, Cy; R¹ = Cy, 1-adamantyl, 3,5-(CF₃)₂C₆H₃, 3,5-Me₂C₆H₃) of the Josiphos family, starting from com. available rhenium sources. These new Re^V oxido and nitrido complexes, several of which have been characterized by x-ray crystallog., are air- and moisture-stable and are active catalysts in the asym. transfer hydrogenation of ketones using 2-propanol as the hydrogen source in the presence of substoichiometric amounts of triethylamine (TEA). The reaction proceeds cleanly with good to excellent yields (50-99 %) but with moderate enantioselectivity (up to 58 % ee). A mechanism not involving hydridic species is proposed. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Electric Literature of C9H9NO).

(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) 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. 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.Electric Literature of C9H9NO

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Highly Enantioselective Hydrosilylation of Ketones Catalyzed by a Chiral Oxazaborolidinium Ion was written by Kang, Byung Chul;Shin, Sung Ho;Yun, Jaesook;Ryu, Do Hyun. And the article was included in Organic Letters in 2017.Application In Synthesis of (R)-4-(1-Hydroxyethyl)benzonitrile This article mentions the following:

A highly enantioselective hydrosilylation of ketones was developed for the synthesis of a variety of chiral secondary alcs. In the presence of a chiral oxazaborolidinium ion (COBI) catalyst, the reaction proceeded with good yields (up to 99%) with excellent enantioselectivities (up to 99% ee). In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Application In Synthesis of (R)-4-(1-Hydroxyethyl)benzonitrile).

(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Application In Synthesis of (R)-4-(1-Hydroxyethyl)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts