Category: 83783-33-9

Talukder, Poulami; Chen, Shengxi; Roy, Basab; Yakovchuk, Petro; Spiering, Michelle M.; Alam, Mohammad P.; Madathil, Manikandadas M.; Bhattacharya, Chandrabali; Benkovic, Stephen J.; Hecht, Sidney M. published their research in Biochemistry on December 29 ,2015. The article was titled 《Cyanotryptophans as Novel Fluorescent Probes for Studying Protein Conformational Changes and DNA-Protein Interaction》.Application of 83783-33-9 The article contains the following contents:

Described herein are the syntheses and photophys. characterization of three novel cyanotryptophans, and their efficient incorporation into proteins as fluorescent probes. Photophys. characteristics indicated that each was significantly brighter and red-shifted in fluorescence emission relative to tryptophan. Each analog was used to activate a suppressor tRNA transcript and was incorporated with good efficiency into two different positions (Trp22 and Trp74) of Escherichia coli dihydrofolate reductase (ecDHFR). The Trp analogs could be monitored selectively in the presence of multiple native Trp residues in DHFR. 6-CNTrp (A) formed an efficient Förster resonance energy transfer (FRET) pair with L-(7-hydroxycoumarin-4-yl)ethylglycine (HCO, D) at position 17. Further, 6-CNTrp (A) was incorporated into two DNA binding proteins, including the Klenow fragment of DNA polymerase I and an RNA recognition motif (RRM2) of heterogeneous nuclear ribonucleoprotein L-like (hnRNP LL). Using these proteins, we demonstrated the use of FRET involving A as a fluorescence donor and benzo[g]quinazoline-2,4-(1H,3H)-dione 2′-deoxyriboside (Tf) or 4-aminobenzo[g]quinazoline-2-one 2′-deoxyriboside (Cf) as fluorescent acceptors to study the binding interaction of the Klenow fragment with duplex DNA oligomers (labeled with Tf), or the domain-specific association between hnRNP LL and the BCL2 i-motif DNA (labeled with Cf). Thus, the non-natural amino acid could be used as a FRET partner for studying protein-nucleic acid interactions. Together, these findings demonstrate the potential utility of 6-CNTrp (A) as a fluorescence donor for the study of protein conformational events. In the experimental materials used by the author, we found 3-Formyl-1H-indole-6-carbonitrile(cas: 83783-33-9Application of 83783-33-9)

3-Formyl-1H-indole-6-carbonitrile(cas: 83783-33-9) is a member of nitriles. Nitriles have been reduced to amines by many methods, especially by catalytic hydrogenation and by metal hydrides. Aliphatic and aromatic nitriles have also been reduced to nitro derivatives using hydrazinium monoformate in the presence of Raney-nickel.Application of 83783-33-9

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Su, Ting; Naughton, Mary Ann H.; Smyth, Mark S.; Rose, Jack W.; Arfsten, Ann E.; McCowan, Jefferson R.; Jakubowski, Joseph A.; Wyss, Virginia L.; Ruterbories, Kenneth J.; Sall, Daniel J.; Scarborough, Robert M. published their research in Journal of Medicinal Chemistry on December 19 ,1997. The article was titled 《Fibrinogen Receptor (GPIIb-IIIa) Antagonists Derived from 5,6-Bicyclic Templates. Amidinoindoles, Amidinoindazoles, and Amidinobenzofurans Containing the N-α-Sulfonamide Carboxylic Acid Function as Potent Platelet Aggregation Inhibitors》.Synthetic Route of C10H6N2O The article contains the following contents:

A series of highly potent and specific fibrinogen receptor antagonists have been discovered and optimized through structural modification of novel amidinoindole and benzofuran compounds Systematic linker optimization afforded the amidinobenzofuran-containing inhibitor 3-[[3-(5-amidino-2-benzofurancarboxamido)propionyl]amino]-3-phenylpropionic acid (I), which displayed an IC50 value of 250 nM in platelet aggregation assays. Attempts to enhance activity by modifying the β-position of β-alaninate of inhibitor I had only a modest effect on inhibitory activity in aggregation assays. Analogs prepared to enhance the activity by conformational restriction were also found to be equally or less potent. In contrast, modification at the α-position of β-alaninate resulted in the identification of extremely potent and novel amidinobenzofuran-containing derivatives Reexamination of 5,6-bicyclic aromatic nucleus led to the further identification of amidinoindole- and amidinoindazole-containing derivatives These analogs exhibited potent in vitro activity with IC50 values of 25-65 nM in platelet aggregation assays and an IC50 value of 2 nM in fibrinogen binding assays and demonstrated a selectivity of >50,000-fold for GPIIb-IIIa vs. the most closely related integrin, the vitronectin receptor, αvβ3. In the experiment, the researchers used 3-Formyl-1H-indole-6-carbonitrile(cas: 83783-33-9Synthetic Route of C10H6N2O)

3-Formyl-1H-indole-6-carbonitrile(cas: 83783-33-9) is a member of nitriles. Nitriles have been reduced to amines by many methods, especially by catalytic hydrogenation and by metal hydrides. Aliphatic and aromatic nitriles have also been reduced to nitro derivatives using hydrazinium monoformate in the presence of Raney-nickel.Synthetic Route of C10H6N2O

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《Aromatic amidines. Comparison of their ability to block respiratory syncytial virus induced cell fusion and to inhibit plasmin, urokinase, thrombin, and trypsin》 were Tidwell, R. R.; Geratz, J. D.; Dubovi, E. J.. And the article was published in Journal of Medicinal Chemistry in 1983. Category: nitriles-buliding-blocks The author mentioned the following in the article:

The title compounds I (R = H, H2NC:NH, NO2; R1 = H or H2NC:NH; R2 = H, Me, Et, benzyl, substituted benzyl; R3 = H, COEt; R4 = H, COH, Ac, COCF3, or Bz) some of which were prepared from the corresponding nitrile derivatives and benzimidazoles by a modified Pinner amidine synthesis, and investigated to determine if the correlation between inhibition of plasmin  [9001-90-5] and(or) urokinase  [9039-53-6] with fusion-blocking activity exists with these compounds 6-amidino-1H-indole-3-carboxaldehyde  [83783-19-1] Was a selective inhibitor of plasmin over thrombin  [9002-04-4], and 5-amidino-1-(4-amidino-2-chlorobenzyl)-1H-indole  [80531-08-4] is a potent new blocker of virus-induced cell fusion. In the experimental materials used by the author, we found 3-Formyl-1H-indole-6-carbonitrile(cas: 83783-33-9Category: nitriles-buliding-blocks)

3-Formyl-1H-indole-6-carbonitrile(cas: 83783-33-9) is a member of nitriles. Nitriles have been reduced to amines by many methods, especially by catalytic hydrogenation and by metal hydrides. Aliphatic and aromatic nitriles have also been reduced to nitro derivatives using hydrazinium monoformate in the presence of Raney-nickel.Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《Triflic Acid as an Efficient Bronsted Acid Promoter for the Umpolung of N-Ac Indoles in Hydroarylation Reactions》 was published in Advanced Synthesis & Catalysis in 2018. These research results belong to Nandi, Raj Kumar; Perez-Luna, Alejandro; Gori, Didier; Beaud, Rodolphe; Guillot, Regis; Kouklovsky, Cyrille; Gandon, Vincent; Vincent, Guillaume. Safety of 3-Formyl-1H-indole-6-carbonitrile The article mentions the following:

We report that triflic acid, a strong Bronsted acid, is a very powerful alternative to FeCl3 to mediate the hydroarylation of N-Ac indoles, which delivers regioselectively 3-arylindolines, 3,3-spiroindolines or 2-arylindolines. Mechanistic explorations point towards the existence of a highly electrophilic intermediate by simultaneous activation of the acetyl and of the C2=C3 bond by protons. After reading the article, we found that the author used 3-Formyl-1H-indole-6-carbonitrile(cas: 83783-33-9Safety of 3-Formyl-1H-indole-6-carbonitrile)

3-Formyl-1H-indole-6-carbonitrile(cas: 83783-33-9) is a member of nitriles. Nitriles have been reduced to amines by many methods, especially by catalytic hydrogenation and by metal hydrides. Aliphatic and aromatic nitriles have also been reduced to nitro derivatives using hydrazinium monoformate in the presence of Raney-nickel.Safety of 3-Formyl-1H-indole-6-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Wu, Wenliang; Su, Weiping published their research in Journal of the American Chemical Society on August 10 ,2011. The article was titled 《Mild and Selective Ru-Catalyzed Formylation and Fe-Catalyzed Acylation of Free (N-H) Indoles Using Anilines as the Carbonyl Source》.Electric Literature of C10H6N2O The article contains the following contents:

Indoles undergo regioselective formylation and acylation reactions with N-methylaniline or N-benzylanilines in the presence of either ruthenium(III) or iron(II) chlorides using tert-Bu hydroperoxide as the oxidant to give 3-formyl or 3-benzoylindoles in 34-86% yields. The processes are operationally simple and compatible with a variety of functional groups. Reaction of indole with N-(13C-methyl)aniline yields 3-(13C-formyl)indole in 70% yield, unambiguously establishing that the carbonyl carbon in the formylation products originates from the Me group of N-Me aniline. In the experiment, the researchers used 3-Formyl-1H-indole-6-carbonitrile(cas: 83783-33-9Electric Literature of C10H6N2O)

3-Formyl-1H-indole-6-carbonitrile(cas: 83783-33-9) is a member of nitriles. Nitriles have been reduced to amines by many methods, especially by catalytic hydrogenation and by metal hydrides. Aliphatic and aromatic nitriles have also been reduced to nitro derivatives using hydrazinium monoformate in the presence of Raney-nickel.Electric Literature of C10H6N2O

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Wu, Wenliang; Su, Weiping published their research in Journal of the American Chemical Society on August 10 ,2011. The article was titled 《Mild and Selective Ru-Catalyzed Formylation and Fe-Catalyzed Acylation of Free (N-H) Indoles Using Anilines as the Carbonyl Source》.Electric Literature of C10H6N2O The article contains the following contents:

Indoles undergo regioselective formylation and acylation reactions with N-methylaniline or N-benzylanilines in the presence of either ruthenium(III) or iron(II) chlorides using tert-Bu hydroperoxide as the oxidant to give 3-formyl or 3-benzoylindoles in 34-86% yields. The processes are operationally simple and compatible with a variety of functional groups. Reaction of indole with N-(13C-methyl)aniline yields 3-(13C-formyl)indole in 70% yield, unambiguously establishing that the carbonyl carbon in the formylation products originates from the Me group of N-Me aniline. In the experiment, the researchers used 3-Formyl-1H-indole-6-carbonitrile(cas: 83783-33-9Electric Literature of C10H6N2O)

3-Formyl-1H-indole-6-carbonitrile(cas: 83783-33-9) is a member of nitriles. Nitriles have been reduced to amines by many methods, especially by catalytic hydrogenation and by metal hydrides. Aliphatic and aromatic nitriles have also been reduced to nitro derivatives using hydrazinium monoformate in the presence of Raney-nickel.Electric Literature of C10H6N2O

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《nBu4NI-catalyzed C3-formylation of indoles with N-methylaniline》 were Li, Lan-Tao; Huang, Juan; Li, Hong-Ying; Wen, Li-Juan; Wang, Peng; Wang, Bin. And the article was published in Chemical Communications (Cambridge, United Kingdom) in 2012. Synthetic Route of C10H6N2O The author mentioned the following in the article:

NBu4NI-catalyzed C3-selective formylation of N-H and N-substituted indoles by using N-methylaniline as a formylating reagent was first successfully demonstrated. The experimental process involved the reaction of 3-Formyl-1H-indole-6-carbonitrile(cas: 83783-33-9Synthetic Route of C10H6N2O)

3-Formyl-1H-indole-6-carbonitrile(cas: 83783-33-9) is a member of nitriles. Nitriles have been reduced to amines by many methods, especially by catalytic hydrogenation and by metal hydrides. Aliphatic and aromatic nitriles have also been reduced to nitro derivatives using hydrazinium monoformate in the presence of Raney-nickel.Synthetic Route of C10H6N2O

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Marcin, Lawrence R.; Higgins, Mendi A.; Zusi, F. Christopher; Zhang, Yunhui; Dee, Michael F.; Parker, Michael F.; Muckelbauer, Jodi K.; Camac, Daniel M.; Morin, Paul E.; Ramamurthy, Vidhyashankar; Tebben, Andrew J.; Lentz, Kimberley A.; Grace, James E.; Marcinkeviciene, Jovita A.; Kopcho, Lisa M.; Burton, Catherine R.; Barten, Donna M.; Toyn, Jeremy H.; Meredith, Jere E.; Albright, Charles F.; Bronson, Joanne J.; Macor, John E.; Thompson, Lorin A. published an article in Bioorganic & Medicinal Chemistry Letters. The title of the article was 《Synthesis and SAR of indole- and 7-azaindole-1,3-dicarboxamide hydroxyethylamine inhibitors of BACE-1》.Recommanded Product: 3-Formyl-1H-indole-6-carbonitrile The author mentioned the following in the article:

Heterocyclic replacement of the isophthalamide Ph ring in hydroxyethylamine (HEA) BACE-1 inhibitors was explored. A variety of indole-1,3-dicarboxamide HEAs I (X = CH; R1 = R2 = Et, n-Pr, n-Bu; R1 = n-Bu, R2 = H, Me; R3 = H, F, CN; R4 = H, F, Cl, CF3, CO2H, etc.; R5 = 3-MeOC6H4CH2; R6 = H, F) exhibited potent BACE-1 enzyme inhibition, but displayed poor cellular activity. Improvements in cellular activity and aspartic protease selectivity were observed for 7-azaindole-1,3-dicarboxamide HEAs I (X = N; R1 = Bu, n-pentyl, isopentyl, MeOCH2CH2, R2 = Me; R1 = cyclopropylmethyl, R2 = n-Pr; R1R2N = 2-ethoxymethyl-1-piperidinyl, etc.; R3 = R4 = H; R5 = 3-MeOC6H4CH2, 3-MeOC6H4CO, cyclopropyl, etc.; R6 = H, F). A methylprolinol-bearing azaindole I [X = N; R1R2N = (R)-2-methoxymethyl-1-pyrrolidinyl; R3 = R4 = H; R5 = 3-MeOC6H4CH2; R6 = F] demonstrated robust reductions in rat plasma Aβ levels, but did not lower rat brain Aβ due to poor central exposure. The same compound exhibited a high efflux ratio in a bidirectional Caco-2 assay and was likely a substrate of the efflux transporter P-glycoprotein. X-ray crystal structures are reported for two indole HEAs in complex with BACE-1. In the experiment, the researchers used many compounds, for example, 3-Formyl-1H-indole-6-carbonitrile(cas: 83783-33-9Recommanded Product: 3-Formyl-1H-indole-6-carbonitrile)

3-Formyl-1H-indole-6-carbonitrile(cas: 83783-33-9) is a member of nitriles. Nitriles have been reduced to amines by many methods, especially by catalytic hydrogenation and by metal hydrides. Aliphatic and aromatic nitriles have also been reduced to nitro derivatives using hydrazinium monoformate in the presence of Raney-nickel.Recommanded Product: 3-Formyl-1H-indole-6-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts