Category: nitriles-buliding-blocks

Magic matrices for ionization in mass spectrometry was written by Trimpin, Sarah;Lutomski, Corinne A.;El-Baba, Tarick J.;Woodall, Daniel W.;Foley, Casey D.;Manly, Cory D.;Wang, Beixi;Liu, Chih-Wei;Harless, Bryan M.;Kumar, Ruby;Imperial, Lorelie F.;Inutan, Ellen D.. And the article was included in International Journal of Mass Spectrometry in 2015.Category: nitriles-buliding-blocks This article mentions the following:

The initial discovery that a heated inlet tube of a mass spectrometer is an ionization source producing ions from volatile, nonvolatile, small, and large mols. with charge states similar to electrospray ionization has been advanced to ionization requiring only the vacuum inherent with a mass spectrometer and a suitable matrix. This spontaneous ionization method was first applicable with the matrix 3-nitrobenzonitrile. Here we report that over 40 compounds have now been discovered that spontaneously convert mols. to gas-phase ions when exposed to sub-atm. pressure, some with remarkable sensitivity (10 fmol of protein insulin). The commonality of all matrixes is the ability to sublime, preferably near room temperature, through exposure to vacuum, and the ability to create charge separation under these conditions. The effect of vacuum, airflow, temperature (-80 to +150 °C) and pH (1-9) on the effectiveness of these newly discovered matrixes to ionize peptides and proteins is presented. Compounds with and without acidic hydrogen atoms act as matrixes and ionize specific compound classes. The new matrixes extend applications from peptides, proteins and drugs to compound classes without basic functionality such as lipids and synthetic polymers in the neg. and pos. modes. Mass resolution and ion mobility spectrometry aspects are also discussed. In the experiment, the researchers used many compounds, for example, 5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6Category: nitriles-buliding-blocks).

5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6) belongs to nitriles. The R-C-N bond angle in and nitrile is 180° which give a nitrile functional group a linear shape. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two π bond in the triple bond. 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. Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Pyridyl Radical Cation for C-H Amination of Arenes was written by Roessler, Simon L.;Jelier, Benson J.;Tripet, Pascal F.;Shemet, Andrej;Jeschke, Gunnar;Togni, Antonio;Carreira, Erick M.. And the article was included in Angewandte Chemie, International Edition in 2019.Category: nitriles-buliding-blocks This article mentions the following:

Electron-transfer photocatalysis provides access to the elusive and unprecedented N-pyridyl radical cation from selected N-substituted pyridinium reagents. The resulting C(sp²)-H functionalization of (hetero)arenes furnishes versatile intermediates for the development of valuable aminated aryl scaffolds. Mechanistic studies that include the first spectroscopic evidence of a spin-trapped N-pyridyl radical adduct implicate SET-triggered, pseudo-mesolytic cleavage of the N-X pyridinium reagents mediated by visible light. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methoxybenzonitrile (cas: 60979-25-1Category: nitriles-buliding-blocks).

3-Amino-4-methoxybenzonitrile (cas: 60979-25-1) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. 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.Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Highly efficient conjugate reduction of α,β-unsaturated nitriles catalyzed by copper/xanthene-type bisphosphine complexes was written by Kim, Daesung;Park, Bu-Mahn;Yun, Jaesook. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2005.COA of Formula: C8H13N This article mentions the following:

α,β-Unsaturated nitriles are chemoselectively reduced to the corresponding saturated nitriles in high yields using a copper-DPEphos or Xantphos complex as catalyst in the presence of polymethylhydrosiloxane (PMHS) as the stoichiometric reducing agent and tert-butanol as additive. The use of tert-butanol as additive was key to success of this method. PMHS was used as stoichiometric reducing agent. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7COA of Formula: C8H13N).

2-Cyclohexylacetonitrile (cas: 4435-14-7) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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. COA of Formula: C8H13N

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Design, synthesis, biological evaluation and molecular modeling study of new thieno[2,3-d]pyrimidines with anti-proliferative activity on pancreatic cancer cell lines was written by Salem, Mohamed S. H.;Abdel Aziz, Yasmine M.;Elgawish, Mohamed S.;Said, Mohamed M.;Abouzid, Khaled A. M.. And the article was included in Bioorganic Chemistry in 2020.Safety of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile This article mentions the following:

In this study, twenty eight new compounds based on thieno[2,3-d]pyrimidine scaffold I [R = (2-methylphenyl)aminyl, diphenylaminyl, 2-naphthyloxy, etc.] and II [X = O, S; R¹ = Ph, 4-fluorophenyl, ethyl] were synthesized as anti-pancreatic cancer agents mimicking the benzofuro[3,2-d]pyrimidine derivative, amuvatinib. Various linkers including amides, esters, ketones, urea and thiourea derivatives were utilized to study their effect on the anti-proliferative activity of these compounds Most of the tested compounds revealed good cytotoxic activities against pancreatic carcinoma cell line PANC-1. Compound I [R = (4-chlorophenyl)aminyl] (A) showed the highest cytotoxicity with an IC₅₀ value of 5.4μM. Furthermore, (A) showed excellent platelet derived growth factor receptor (PDGFR-α) inhibitory activity, with IC₅₀ value 0.155μM. Docking study was carried out into PDGFR-α active site which showed comparable binding mode to that of FDA approved PDGFR-α inhibitor, imatinib. 3D-Quant. structure activity relationship (QSAR) model was built up with five-featured pharmacophore which could be implemented for emerging effective lead structures. These compounds could serve as a new chemotype for discovering new agents for pancreatic cancer therapy. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Safety of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) 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.Safety of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Antioxidant-based inhibitors of leukotriene biosynthesis. The discovery of 6-[1-[2-(hydroxymethyl)phenyl]-1-propen-3-yl]-2,3-dihydro-5-benzofuranol, a potent topical antiinflammatory agent was written by Hammond, Milton L.;Zambias, Robert A.;Chang, Michael N.;Jensen, Norman P.;McDonald, John;Thompson, Kathryn;Boulton, David A.;Kopka, Ihor E.;Hand, Karen M.. And the article was included in Journal of Medicinal Chemistry in 1990.Synthetic Route of C5H2N2O2S This article mentions the following:

The leukotrienes, metabolites of arachidonic acid produced through the action of the enzyme 5-lipoxygenase, are important mediators of immediate hypersensitivity and inflammation. Among the variety of diseases in which the leukotrienes may play a symptomatic or causative role is the dermatol. condition psoriasis, a chronic proliferative disease of the skin. This study reports the synthesis and comparative biol. activities of various ortho-substituted phenols including 4-methoxyphenols, 6-hydroxy-1,2,3,4-tetrahydrobenzopyrans, 2,3-dihydro-5-benzofuranols, and 5-benzofuranols. The phenols prepared in this study were evaluated for their ability to inhibit the production of leukotriene B₄ (LTB₄) in isolated human polymorphonuclear leukocytes (PMNs) and to inhibit a topical inflammatory response in the topical mouse ear (TME) model. In the former case, when the log IC₅₀ was plotted vs. the log of the octanol/water partition coefficient (log P), to eliminate the effect of lipophilicity, the 2,3-dihydro-5-benzofuranol ring system was more potent than the other ring systems examined throughout the range of partition coefficients studied. The ability to inhibit leukotriene production in vitro in human PMNs can be rationalized on the basis of a model that suggests that the observed inhibition is dependent on the kinetic ability of the inhibitor to reduce a radical species and on the fraction of inhibitor that is partitioned into the cell membrane. While the in vivo antiinflammatory activity as measured by the TME did not correlate with the in vitro data, it was felt that the TME represented a valuable measure of the ability of a compound to penetrate the skin to the site of an ongoing inflammatory response. The title compound I was chosen for further development. In the experiment, the researchers used many compounds, for example, 4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6Synthetic Route of C5H2N2O2S).

4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6) 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Synthetic Route of C5H2N2O2S

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

N-Demethylation of N,N-Dimethylanilines by the Benzotriazole N-Oxyl Radical: Evidence for a Two-Step Electron Transfer-Proton Transfer Mechanism was written by Baciocchi, Enrico;Bietti, Massimo;Lanzalunga, Osvaldo;Lapi, Andrea;Raponi, Daniele. And the article was included in Journal of Organic Chemistry in 2010.COA of Formula: C9H10N2 This article mentions the following:

The reaction of the benzotriazole N-oxyl radical (BTNO) with a series of 4-X-N,N-dimethylanilines (X = CN, CF₃, CO₂CH₂CH₃, CH₃, OC₆H₅, OCH₃) has been investigated in CH₃CN. Product anal. shows that the radical, 4-X-C₆H₄N(CH₃)CH₂^·, is first formed, which can lead to the N-demethylated product or the product of coupling with BTNO. Reaction rates were found to increase significantly by increasing the electron-donating power of the aryl substituents (ρ⁺ = -3.8). With electron-donating substituents (X = CH₃, OC₆H₅, OCH₃), no intermol. deuterium kinetic isotope effect (DKIE) and a substantial intramol. DKIE are observed With electron-withdrawing substituents (X = CN, CF₃, CO₂CH₂CH₃), substantial values of both intermol. and intramol. DKIEs are observed These results can be interpreted on the basis of an electron-transfer mechanism from the N,N-dimethylanilines to the BTNO radical followed by deprotonation of the anilinium radical cation (ET-PT mechanism). By applying the Marcus equation to the kinetic data for X = CH₃, OC₆H₅, OCH₃ (rate-determining ET), a reorganization energy for the ET reaction was determined (λ_BTNO/DMA = 32.1 kcal mol^-1). From the self-exchange reorganization energy for the BTNO/BTNO^– couple, a self-exchange reorganization energy value of 31.9 kcal mol^-1 was calculated for the DMA^·1/DMA couple. In the experiment, the researchers used many compounds, for example, 4-(Ethylamino)benzonitrile (cas: 4714-63-0COA of Formula: C9H10N2).

4-(Ethylamino)benzonitrile (cas: 4714-63-0) 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. COA of Formula: C9H10N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A cost-effective and green aqueous synthesis of 3-substituted coumarins catalyzed by potassium phthalimide was written by Kiyani, Hamzeh;Daroonkala, Masoumeh Darzi. And the article was included in Bulletin of the Chemical Society of Ethiopia in 2015.Related Products of 51473-74-6 This article mentions the following:

An efficient procedure for the synthesis of various 3-substituted coumarins I [R = H, 6-Br, 7-NEt₂, 8-OMe; R¹ = CN, COOH; X = O] as well as 2-imino-2H-chromenes I [R¹ = CN; X = NH] was developed via potassium phthalimide-catalyzed Knoevenagel condensation reaction of salicylaldehydes with active methylene compounds under aqueous conditions at room temperature This approach provided many merits such as high yields of products, simple work-up procedure, waste free and mild reaction conditions, com. available organocatalyst and the use of water as environmentally benign solvent. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Related Products of 51473-74-6).

7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6) 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. 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.Related Products of 51473-74-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Rearrangement of the bromine atom in the demethylation of bromomethoxybenzoic acid. IV. 2-Bromoanisic acid and 3-bromoanisic acid was written by Tomita, Masao;Fujitani, Kazuyoshi. And the article was included in Yakugaku Zasshi in 1956.Related Products of 82380-17-4 This article mentions the following:

2,4-Br(MeO)C₆H₃CO₂H (XI), needles, m. 197-8°, was synthesized from 4-O₂NC₆H₄Me or p-cresol as a raw material. Nitration of 3-BrC₆H₄OH gave 3,4-Br(O₂N)C₆H₃OH, m. 125-31°, which was reduced to 3,4-Br(H₂N)C₆H₃OH, m. 151°; this was diazotized and treated with CuCN yielding 2,4-Br(HO)C₆H₃CN (XII), m. 151°. XI (0.5 g.), 15 ml. PhCl, and 2 g. AlCl₃ heated 1.5 hrs. on a water bath and the product poured on ice and extracted with Et₂O gave 0.3 g. 2,4-Br(HO)C₆H₃CO₂H (XIII), needles, m. 206-8° (from water); the m.p. of XIII given as 151° by Hodgson and Jenkinson (cf. C.A. 22,949) was confirmed to be the m.p. of XII. XI (1 g.) and 7 ml. HBr-AcOH in a sealed tube heated 5 hrs. at 130° and 2 hrs. at 150°, the product concentrated, neutralized with NaHCO₃ to remove the acidic substance, extracted with Et₂O, stirred with NaOH, and the NaOH layer acidified with HCl and extracted with Et₂O gave 3-BrC₆H₄OH (benzoate, m. 84-5°) and a small amount of XIII, m. 206-8°. XI (0.5 g.) and 6 ml. HCl-AcOH in a sealed tube heated 12 hrs. at 150° gave 0.45 g. XI. 2,4-Br(MeO)C₆H₃CO₂Me (XIV), plates, m. 29°, (1 g.) and 7 ml. HBr-AcOH in a sealed tube heated and the product treated as usual gave 3-BrC₆H₄OH. Similarly, 3,4-Br(MeO)C₆H₃CO₂H gave 3,4-Br(HO)C₆H₃CO₂H, m. 106-7°. 3,4-Br(MeO)C₆H₃CO₂Me (0.5 g.) gave 0.3 g. 3,5,4-Br₂(HO)C₆H₂CO₂H, m. 253-7° (decomposition), and 0.1 g. 3,4-Br(HO)C₆H₃CO₂H, m. 175-7° (Me ester, m. 107°). In the experiment, the researchers used many compounds, for example, 2-Bromo-4-hydroxybenzonitrile (cas: 82380-17-4Related Products of 82380-17-4).

2-Bromo-4-hydroxybenzonitrile (cas: 82380-17-4) 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. 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.Related Products of 82380-17-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Design and synthesis of novel tranilast analogs: Docking, antiproliferative evaluation and in-silico screening of TGFβR1 inhibitors was written by Ismail, Magda M. F.;El-Zahabi, Heba S. A.;Ibrahim, Rabab S.;Mehany, Ahmed B. M.. And the article was included in Bioorganic Chemistry in 2020.Recommanded Product: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile This article mentions the following:

This work summarizes design, synthesis and biol. evaluation of sixteen novel tranilast analogs I [X = F, Cl, Br], II [X = F, O₂N], [X = H, Me; R¹ = OMe, Cl; R² = H, Cl], IV [Ar = 2-thiophenyl, 2,4-dimethylphenyl, 4-pyridinyl] and V [R = cyano, ethoxycarbonyl] on different tumors such as PC-3, HepG-2 and MCF-7 cell lines. The in-vitro cytotoxicity was evaluated using MTT assay showed that, twelve compounds out of sixteen showed higher cytotoxic activities (IC₅₀‘s 1.1-6.29μM), than that of the reference standard, 5-FU (IC₅₀ 7.53μM). The promising cytotoxic hits II [X = F], IV [Ar = 2-thiophenyl] and V [R = CN, X = 2,5-dimethoxy, n = 1; R = CN, X = OH, 2,5-dimethoxy, n = 0] proved to be selective to cancer cells when their cytotoxicity’s are examined on human normal cell line (WI-38). Then they were investigated for their possible mode of action as TGFβR1 inhibitors; remarkable inhibition of TGFβR1 by these hits was observed at the range of IC₅₀ 0.087-3.276μM. The cell cycle anal. of the most potent TGFβR1 inhibitor, II [X = O₂N] revealed cell cycle arrest at G2/M phase on prostate cancer cells. Addnl., it was clearly indicated apoptosis induction at Pre-G1 phase, this was substantiated by significant increase in the expression on the tumor suppressor gene, p53 and up regulation the level of apoptosis mediator, caspase-3. In addition, in-silico study was performed for validating the physicochem. and ADME properties which revealed that, all compounds were orally bioavailable with no side effects complying with Lipinski rule. The proposed mode of action was further explored on the light of mol. modeling simulation of the most potent compounds, II [X = O₂N] and V [n = 0, R = CN, X = 2,5-dimethoxy] which were docked into the active sites of TGFβR1 to predict their affinities toward the receptor. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Recommanded Product: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) belongs to nitriles. Nitrile carbon shifts are in the range of 115�25 ppm whereas in isonitriles the shifts are around 155�65 ppm. 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: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Phototranspositions of cyanothiophenes: permutation pattern analysis and the chemical trapping of an intermediate 5-thiabicyclo[2.1.0]pent-2-ene was written by Barltrop, John A.;Day, A. Colin;Irving, Edward. And the article was included in Journal of the Chemical Society, Chemical Communications in 1979.SDS of cas: 55406-13-8 This article mentions the following:

Through their first excited singlet states, cyanothiophenes undergo phototranspositions for which permutation pattern anal. and the isolation of furan-thiabicyclopentene adducts (from irradiation in furan), suggest a mechanism involving 2,5-bonding followed by a ‘walk’ of the S atom. E.g., irradiation of 3-cyanothiophene in furan gave 71 and 7% resp., of the 1:1 adducts I and II. This result provides evidence for the intermediate III, for which I and II are the expected Diels-Alder adducts with furan; a similar result occurred with 2-cyanothiophene. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8SDS of cas: 55406-13-8).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) belongs to nitriles. The R-C-N bond angle in and nitrile is 180° which give a nitrile functional group a linear shape. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two π bond in the triple bond. 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. SDS of cas: 55406-13-8

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts