Tag: 100-200

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

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

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

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

Triazoloquinazolines as a novel class of phosphodiesterase 10A (PDE10A) inhibitors was written by Kehler, Jan;Ritzen, Andreas;Langgard, Morten;Petersen, Sebastian Leth;Farah, Mohamed M.;Bundgaard, Christoffer;Christoffersen, Claus Tornby;Nielsen, Jacob;Kilburn, John Paul. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2011.Category: nitriles-buliding-blocks This article mentions the following:

Novel triazoloquinazolines have been found as phosphodiesterase 10A (PDE10A) inhibitors. Structure-activity studies improved the initial micromolar potency which was found in the lead compound by a 100-fold identifying 5-(1H-benzoimidazol-2-ylmethylsulfanyl)-2-methyl-[1,2,4]triazolo[1,5-c]quinazoline, 42 (PDE10A IC₅₀ = 12 nM) as the most potent compound from the series. Two X-ray structures revealed novel binding modes to the catalytic site of the PDE10A enzyme. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Category: nitriles-buliding-blocks).

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) 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. 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.Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Development of Inhibitors of SAICAR Synthetase (PurC) from Mycobacterium abscessus Using a Fragment-Based Approach was written by Charoensutthivarakul, Sitthivut;Thomas, Sherine E.;Curran, Amy;Brown, Karen P.;Belardinelli, Juan M.;Whitehouse, Andrew J.;Acebron-Garcia-de-Eulate, Marta;Sangan, Jaspar;Gramani, Subramanian G.;Jackson, Mary;Mendes, Vitor;Floto, R. Andres;Blundell, Tom L.;Coyne, Anthony G.;Abell, Chris. And the article was included in ACS Infectious Diseases in 2022.Recommanded Product: 60025-09-4 This article mentions the following:

In this study, SAICAR synthetase (PurC) from Mab was identified as a promising target for novel antibiotics. An inhouse fragment library screen and a high-throughput X-ray crystallog. screen of diverse fragment libraries were explored to provide crucial starting points for fragment elaboration. A series of compounds developed from fragment growing and merging strategies, guided by crystallog. information and careful hit-to-lead optimization, have achieved potent nanomolar binding affinity against the enzyme. Some compounds also show a promising inhibitory effect against Mab and Mtb. This work utilizes a fragment-based design and demonstrates for the first time the potential to develop inhibitors against PurC from Mab. In the experiment, the researchers used many compounds, for example, 4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4Recommanded Product: 60025-09-4).

4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4) 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.Recommanded Product: 60025-09-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Hydrogenation of alkenes over nickel nanoparticles under atmospheric pressure of hydrogen was written by Mokhov, V. M.;Popov, Yu. V.;Nebykov, D. N.. And the article was included in Russian Journal of Organic Chemistry in 2016.Reference of 4435-14-7 This article mentions the following:

Nickel nanoparticles are an accessible catalyst which allows hydrogenation of unsaturated compounds to be accomplished under atm. pressure of hydrogen at relatively low temperatures Linear and cyclic alkenes, styrene and norbornene derivatives, as well as pinenes and camphene were smoothly hydrogenated under these conditions. In some cases, selective hydrogenation of unsaturated carbon-carbon bond is possible with the other functional group remaining intact. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Reference of 4435-14-7).

2-Cyclohexylacetonitrile (cas: 4435-14-7) 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.Reference of 4435-14-7

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Highly recoverable organoruthenium-functionalized mesoporous silica boosts aqueous asymmetric transfer hydrogenation reaction was written by Liu, Rui;Cheng, Tanyu;Kong, Lingyu;Chen, Chen;Liu, Guohua;Li, Hexing. And the article was included in Journal of Catalysis in 2013.Synthetic Route of C9H9NO This article mentions the following:

Exploring functionalized mesoporous silica to achieve enhanced catalytic activity and enantioselectivity in heterogeneous asym. catalysis presents a significant challenge that is critical for understanding the function of support and controlling chiral complexation behavior. In this contribution, by cooperative assembly of chiral 4-((trimethoxysilyl)ethyl)phenylsulfonyl-1,2-diphenylethylene-diamine and tetraethoxysilane followed by complexation with organoruthenium complex, we report a unique three-dimensional chiral organoruthenium-functionalized chrysanthemum-like mesoporous silica (CMS). As demonstrated in the studies, taking advantage of the active site-isolated chiral organoruthenium catalytic nature, this heterogeneous catalyst ArRuTsDPEN-CMS (Ar = hexamethylbenzene, TsDPEN = 4-methylphenylsulfonyl-1,2-diphenylethylene-diamine) displays enhanced catalytic activity and enantioselectivity in aqueous asym. transfer hydrogenation with extensive substrates. Furthermore, this heterogeneous catalyst can be conveniently recovered and reused at least 10 times without loss of its catalytic efficiency. These features render this catalyst particularly attractive in practice of organic synthesis in an environmentally friendly manner. Also, this outcome from the study clearly shows that the strategy described here offers a general approach to immobilization of chiral ligand-derived silane onto a functionalized mesoporous material with significant improving catalytic activity. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Synthetic Route of C9H9NO).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A facile microwave assisted synthesis and anti-inflammatory activity of thiophene[3,2- e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one derivatives was written by Kaur, Rajwinder;Rao, Akkinepally Raghuram;Chadha, Renu;Thakur, Nishant;Goswami, Manish. And the article was included in International Journal of Pharmaceutical Sciences Review and Research in 2016.Category: nitriles-buliding-blocks This article mentions the following:

A series of novel substituted triazolo thieno pyrimidines (5-12) was synthesized by employing innovative synthetic methods. Two methods (A and B) were employed for the synthesis of compounds 3-12. Method B (microwave assisted) was found to be facile, economic and less time consuming compared to conventional method (method A) adopted. The microwave irradiation provided an environment-friendly, remarkable rate of acceleration for the reaction with reduced reaction time and in some cases (under MW irradiation) the yields are also substantially higher. Anti-inflammatory activity and mast cell degranulation studies of synthesized compounds were carried out. Indomethacin was taken as a reference standard in carrageenan induced rat paw edema model for anti-inflammatory studies and in mast cell degranulation studies disodium cromoglycate was used for comparison. All compounds showed a good anti-inflammatory response and mast cell stabilization. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Category: nitriles-buliding-blocks).

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. 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.Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis and antiallergy activity of [1,3,4]thiadiazolo[3,2-a]-1,2,3-triazolo[4,5-d]pyrimidin-9(3H)-one derivatives. II. 6-Alkyl- and 6-cycloalkylalkyl derivatives was written by Yokohama, Shuichi;Miwa, Tamotsu;Aibara, Shunzo;Fujiwara, Hiroyuki;Matsumoto, Hiroo;Nakayama, Kiyoshi;Iwamoto, Teiji;Mori, Mikio;Moroi, Reimei. And the article was included in Chemical & Pharmaceutical Bulletin in 1992.Application In Synthesis of 2-Cyclohexylacetonitrile This article mentions the following:

A series of 6-alkyl- or 6-(cycloalkylalkyl)-[1,3,4]thiadiazolo[3,2-a]-1,2,3-triazolo[4,5-d]pyrimidin-9(3H)-ones, including I (R = cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylpropyl, cycloheptylethyl, cyclooctylethyl, cyclododecylethyl), was synthesized from the corresponding 1,3,4-thiadiazol-5-amines II and the antiallergic activities of the products were evaluated. Among these compounds 6-(2-cyclohexylethyl)-[1,3,4]thiadiazolo[3,2-a]-1,2,3-triazolo[4,5-d]pyrimidin-9(3H)-one (I, R = cyclohexylethyl), whose x-ray crystallog. stereostructure was determined, is a promising new antiallergic agent, which has low toxicity and dual activity as a leukotriene D₄ receptor antagonist and as an orally active mast cell stabilizer. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Application In Synthesis of 2-Cyclohexylacetonitrile).

2-Cyclohexylacetonitrile (cas: 4435-14-7) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. 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.Application In Synthesis of 2-Cyclohexylacetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts