Month: January 2023

Antileishmanial activity of new thiophene-indole hybrids: Design, synthesis, biological and cytotoxic evaluation, and chemometric studies was written by Felix, Mayara B.;de Souza, Edson R.;de Lima, Maria do C. A.;Frade, Daiana Karla G.;Serafim, Vanessa de L.;Rodrigues, Klinger Antonio da F.;Neris, Patricia Lima do N.;Ribeiro, Frederico F.;Scotti, Luciana;Scotti, Marcus T.;de Aquino, Thiago M.;Junior, Francisco Jaime B. Jr.;de Oliveira, Marcia R.. And the article was included in Bioorganic & Medicinal Chemistry in 2016.SDS of cas: 70291-62-2 This article mentions the following:

In the present work, thirty-two hybrid compounds containing cycloalka[b]thiophene and indole moieties (TN5, TN5 1-7, TN6, TN6 1-7, TN7, TN7 1-7, TN8, TN8 1-7) were designed, synthesized and evaluated for their cytotoxic and antileishmanial activity against Leishmania amazonensis promastigotes. More than half of the compounds (18 compounds) exhibited significant antileishmanial activity (IC₅₀ lower than 10.0 μg/L), showing better performance than the reference drugs (tri- and penta-valent antimonials). The most active compounds were TN8-7, TN6-1 and TN7 with resp. IC₅₀ values of 2.1, 2.3 and 3.2 μg/mL. Demonstrating that all of the compounds were less toxic than the reference drugs, even at the highest evaluated concentration (400 μg/mL), no compound tested presented human erythrocyte cytotoxicity. Compound TN8-7’s effectiveness against a trivalent antimony-resistant culture was demonstrated. It was observed that TN8-7’s antileishmanial activity is associated with DNA fragmentation of L. amazonensis promastigotes. Chemometric studies (CPCA, PCA, and PLS) highlight intrinsic solubility/lipophilicity, and compound size and shape as closely related to activity. The authors’ results suggest that hybrid cycloalka[b]thiophene-indole derivatives may be considered as lead compounds for further development of new drugs for the treatment of leishmaniasis. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2SDS of cas: 70291-62-2).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. 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.SDS of cas: 70291-62-2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Kinetics and mechanism of decarboxylation of cis-carbonato- and bicarbonato(3,3′,3”-triaminotripropylamine)cobalt(III) ions was written by Massoud, Salah S.. And the article was included in Transition Metal Chemistry (London) in 1997.Application In Synthesis of 3,3′,3”-Nitrilotripropanenitrile This article mentions the following:

The acid-catalyzed hydrolysis of [Co(trpn)(CO₃)]⁺ and [Co(trpn)(HCO₃)]²⁺ ions (trpn = 3,3′,3”-triaminotripropylamine) have been studied spectrophotometrically in aqueous 1.0 M HClO₄/NaClO₄. For the carbonato complex, [HClO₄] = 0.02-0.25 M and T = 20-35 °C; for the bicarbonato complex, [HClO₄] = 0.025-0.30 M and T = 25 °C. Both complexes hydrolyze to form the same cis-diaqua species. The rate law for the hydrolysis is d(ln[Co^III])/dt = k₀ + k₁[H₃O⁺]. The values of the rate constants (25 °C), ΔH^‡ (kJ mol^-1) and ΔS^‡ (J mol^-1 K^-1) are:[Co(trpn)(CO₃)]⁺,k₀ = (1.7 ± 0.6) × 10^-4 s^-1, ΔH₀^‡ = 57 ± 21, ΔS₀^‡ = -126 ± 75; k₁ = (1.0 ± 0.1) × 10^-2 M^-1 s^-1, ΔH₁^‡ = 62 ± 8, ΔS₁^‡ = -75 ± 21, and for [Co(trpn)(HCO₃)]²⁺, k₀ = (2.9 ± 0.7) × 10^-4 s^-1, and k₁ = (7.8 ± 1.0) × 10^-2 M^-1 s^-1. The carbonato complex exhibits a deuterium isotope effect with k₁^D/k₁^H = 1.9, consistent with a rapid pre-equilibrium protonation, followed by rate-controlling ring-opening. The rate constants k₀ and k₁ (25 °C and μ = 1.0 M) for the ring-opening decarboxylation of the two systems studied lie within the exptl. error. The results are compared with other related systems and the factors which influence the ring-opening decarboxylation (steric hindrance, ring strain, electron donor ability of the amines) are discussed. The k₁ path is interpreted in terms of concerted ring-opening and bond-making in the highly unstable aquabicarbonato intermediate. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Application In Synthesis of 3,3′,3”-Nitrilotripropanenitrile).

3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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 3,3′,3”-Nitrilotripropanenitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Dual Ligand-Enabled Nondirected C-H Cyanation of Arenes was written by Chen, Hao;Mondal, Arup;Wedi, Philipp;van Gemmeren, Manuel. And the article was included in ACS Catalysis in 2019.Recommanded Product: 29809-13-0 This article mentions the following:

Aromatic nitriles are key structural units in organic chem. and, therefore, highly attractive targets for C-H activation. Herein, the development of an arene-limited, nondirected C-H cyanation based on the use of two cooperatively acting com. available ligands is reported. The reaction enables the cyanation of arenes by C-H activation in the absence of directing groups and is therefore complementary to established approaches. In the experiment, the researchers used many compounds, for example, 5,6,7,8-Tetrahydronaphthalene-1-carbonitrile (cas: 29809-13-0Recommanded Product: 29809-13-0).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Greener coumarin synthesis by Knoevenagel condensation using biodegradable choline chloride was written by Phadtare, Sunanda Balaso;Shankarling, Ganapati Subray. And the article was included in Environmental Chemistry Letters in 2012.Product Details of 51473-74-6 This article mentions the following:

Aqueous catalysis is an innovative task for the sustainable chem. industry. The use of biodegradable catalysts from natural sources may lead to greener reactions. Here, we report the synthesis of coumarin by Knoevenagel condensation using choline chloride as catalyst. Results show that even 10% of choline chloride can catalyze Knoevenagel condensation to yield coumarin in good yields. Almost all reactions proceeded faster, cleaner and in higher yields in aqueous media. Reaction mechanisms are proposed. The choline chloride catalyst was recycled five times without activity or yield decrease. Therefore, the synthesis of coumarin by Knoevenagel condensation using choline chloride as catalyst is a promising alternative to previously used procedures. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Product Details of 51473-74-6).

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. 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.Product Details of 51473-74-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Two Hg(II)-Based Macrocycles Offering Hydrogen Bonding Cavities: Influence of Cavity Structure on Heterogeneous Catalysis was written by Pachisia, Sanya;Gupta, Rajeev. And the article was included in Crystal Growth & Design in 2019.HPLC of Formula: 55490-87-4 This article mentions the following:

We present the synthesis and characterization of two Hg-macrocycles offering H-bonding based cavities of varying dimensions. Both Hg-macrocycles illustrate a noteworthy difference in their catalytic performance that has been related to their cavity structures. This work presents the synthesis and characterization of two Hg-macrocycles offering H-bonding based cavities of varying dimensions. Both Hg-macrocycles illustrated a noteworthy difference in their catalytic performance that has been related to their cavity structures. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4HPLC of Formula: 55490-87-4).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Pharmacophore modeling, 3D-QSAR, synthesis, and anti-lung cancer evaluation of novel thieno[2,3-d][1,2,3]triazines targeting EGFR was written by Elrayess, Ranza;Abdel Aziz, Yasmine M.;Elgawish, Mohamed S.;Elewa, Marwa;Elshihawy, Hosam A.;Said, Mohamed M.. And the article was included in Archiv der Pharmazie (Weinheim, Germany) in 2020.Safety of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile This article mentions the following:

Two series of thieno[2,3-d][1,2,3]triazine derivatives were designed, synthesized, and biol. evaluated as potential epidermal growth factor receptor (EGFR) inhibitors targeting the non-small-cell lung cancer cell line H1299. Most of the synthesized compounds displayed IC₅₀ values ranging from 25 to 58 nM against H1299, which are superior to that of gefitinib (40μM). 3-(5,6,7,8-Tetrahydro-7H-cyclohexa[4:5]thieno[2,3-d]-1,2,3-triazin-4-ylamino)benzene-1,3-diamine (6b) achieved the highest cytotoxic activity against H1299 with an IC₅₀ value of 25 nM; it had the ability to decrease the EGFR concentration in H1299 cells from 7.22 to 2.67 pg/mL. In vitro, the IC₅₀ value of compound 6b was 0.33 nM against EGFR, which is superior to that of gefitinib at 1.9 nM and erlotinib at 4 nM. The three-dimensional quant. structure-activity relationships and mol. modeling studies revealed comparable binding modes of compound 6b, gefitinib, and erlotinib in the EGFR active site. The in silico ADME (absorption, distribution, metabolism, and excretion) prediction parameters of this compound revealed promising pharmacokinetic and physicochem. properties. Moreover, DFT (d. functional theory) calculations showed the high reactivity of compound 6b toward the EGFR compared with other compounds The designed compound 6b might serve as an encouraging lead compound for the discovery of promising anti-lung cancer agents targeting EGFR. 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. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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

ZIF-8 nanoparticles as an efficient and reusable catalyst for the Knoevenagel synthesis of cyanoacrylates and 3-cyanocoumarins was written by Kolmykov, Oleksii;Chebbat, Nassima;Commenge, Jean-Marc;Medjahdi, Ghouti;Schneider, Raphael. And the article was included in Tetrahedron Letters in 2016.Related Products of 51473-74-6 This article mentions the following:

Zeolitic imidazolate framework (ZIF-8) particles with an average size of ca. 355 nm and a sp. surface area of 1786 m².g^-1 were used as an heterogenous catalyst for the Knoevenagel synthesis of α,β-unsaturated cyanoesters and 3-cyanocoumarins. The preparation of 3-cyanocoumarins was efficiently achieved using DMF as the solvent and conducting the condensation at 80°. When the reaction was performed in ethanol, only the intermediates α,β-unsaturated cyanoesters were obtained. The ZIF-8 catalyst could be reused up to five times without any degradation in activity. SEM and XRD analyses demonstrated the high stability of ZIF-8 crystals during the recycling test. 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. 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. 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.Related Products of 51473-74-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Catalytic Asymmetric Addition of Organolithium Reagents to Aldehydes was written by Veguillas, Marcos;Sola, Ricard;Shaw, Luke;Macia, Beatriz. And the article was included in European Journal of Organic Chemistry in 2016.Related Products of 101219-69-6 This article mentions the following:

Herein we report an efficient catalytic system for the titanium-promoted enantioselective addition of organolithium reagents to aldehydes, based on chiral Ar-BINMOL ligands. Unprecedented yields and enantioselectivities are achieved in the alkylation reactions of aliphatic aldehydes. Remarkably, methyllithium can be added to a wide variety of aromatic and aliphatic aldehydes, providing versatile chiral Me carbinol units in a simple one-pot procedure under mild conditions and in very short reaction times. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Related Products of 101219-69-6).

(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) 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. 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 101219-69-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Single-Crystalline, Size, and Orientation Controllable Nanowires and Ultralong Microwires of Organic Semiconductor with Strong Photoswitching Property was written by Jiang, Lang;Fu, Yanyan;Li, Hongxiang;Hu, Wenping. And the article was included in Journal of the American Chemical Society in 2008.COA of Formula: C18H10N2 This article mentions the following:

Single-crystalline, precise size-controlled nanowires and ultralong microwires with lengths reaching several millimeters of 2-anthracen-9-ylmethylenemalonitrile were prepared in large scale by cast assembly. The size and d. of the nanowires and microwires could be controlled by simply adjusting the concentration of the compound in casting solutions More importantly, the formation of these nanowires and microwires showed no substrate and solvent dependence and was orientation controllable. Highly reproducible and sensitive photoresponse characteristics were observed in these nanowires and microwires. Fast and reversible photoswitchers based on multiple or individual single-crystal microwires were fabricated via “multi times gold wire mask moving” technique with switch ratio over 100. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4COA of Formula: C18H10N2).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) 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 addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).COA of Formula: C18H10N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Intramolecular nucleophilic aromatic substitution reaction of 2-carboxamido-3-arylquinazolin-4-ones and its application to the synthesis of secondary aryl amines was written by Fuwa, Haruhiko;Kobayashi, Toshitake;Tokitoh, Takashi;Torii, Yukiko;Natsugari, Hideaki. And the article was included in Synlett in 2004.Reference of 10282-32-3 This article mentions the following:

A novel intramol. nucleophilic aromatic substitution reaction of 2-carboxamido-3-arylquinazolin-4-one derivatives induced by base treatment and its application to the expeditious synthesis of secondary aryl amines, including diaryl amines, are described. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Reference of 10282-32-3).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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 10282-32-3

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts