Category: 22426-30-8

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 2-Cyano-2-methylpropanoic acid, is researched, Molecular C5H7NO2, CAS is 22426-30-8, about Discovery of N-benzyl-N’-(4-piperidinyl)urea CCR5 antagonists as anti-HIV-1 agents (II): Modification of the acyl portion, the main research direction is benzyl piperidine urea preparation antiHIV1 SAR.Recommanded Product: 22426-30-8.

Modification of the acyl moiety in the CCR5 lead mol. 2 led to identification of several new classes of CCR5 antagonists. Antiviral activity and pharmacokinetic properties of the synthesized compounds were evaluated. Structure-activity relationship (SAR) derived from these studies further guided the optimization efforts, ultimately leading to the discovery of 36 (I) with an acceptable drug-like profile.

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

Safety of 2-Cyano-2-methylpropanoic acid. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 2-Cyano-2-methylpropanoic acid, is researched, Molecular C5H7NO2, CAS is 22426-30-8, about β-Aryl nitrile construction via palladium-catalyzed decarboxylative benzylation of α-cyano aliphatic carboxylate salts. Author is Shang, Rui; Huang, Zheng; Xiao, Xiao; Lu, Xi; Fu, Yao; Liu, Lei.

The palladium-catalyzed decarboxylative benzylation of α-cyano aliphatic carboxylate salts with benzyl electrophiles was discovered. This reaction exhibits good functional group compatibility and proceeds under relatively mild conditions. A diverse range of quaternary, tertiary and secondary β-aryl nitriles can be conveniently prepared by this method.

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Discovery of CP-690,550: A Potent and Selective Janus Kinase (JAK) Inhibitor for the Treatment of Autoimmune Diseases and Organ Transplant Rejection, published in 2010-12-23, which mentions a compound: 22426-30-8, Name is 2-Cyano-2-methylpropanoic acid, Molecular C5H7NO2, SDS of cas: 22426-30-8.

There is a critical need for safer and more convenient treatments for organ transplant rejection and autoimmune disorders such as rheumatoid arthritis. Janus tyrosine kinases (JAK1, JAK3) are expressed in lymphoid cells and are involved in the signaling of multiple cytokines important for various T cell functions. Blockade of the JAK1/JAK3-STAT pathway with a small mol. was anticipated to provide therapeutic immunosuppression/immunomodulation. The Pfizer compound library was screened against the catalytic domain of JAK3 resulting in the identification of a pyrrolopyrimidine-based series of inhibitors represented by the hexahydrocarbazolyl pyrrolopyrimidine CP-352,664. Synthetic analogs of CP-352,664 were screened against the JAK enzymes and evaluated in an IL-2 induced T cell blast proliferation assay. Select compounds were evaluated in rodent efficacy models of allograft rejection and destructive inflammatory arthritis. Optimization within this chem. series led to identification of the cyanoacetylpiperidinylamino pyrrolopyrimidine CP-690,550, a potential first-in-class JAK inhibitor for treatment of autoimmune diseases and organ transplant rejection.

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Alkylcyanoacetic acids》. Authors are Hessler, John C..The article about the compound:2-Cyano-2-methylpropanoic acidcas:22426-30-8,SMILESS:CC(C)(C#N)C(O)=O).Computed Properties of C5H7NO2. Through the article, more information about this compound (cas:22426-30-8) is conveyed.

α-Methyl-α-cycanopropionic acid, obtained in 2.5 g. yield from 8.7 g. of the Et ester allowed to stand overnight in running H2o with 9 g. KOH in 100 cc. MeOH, b12 132-5 °, m. 57°; silver. salt; barium salt, prisms with 18 mols. H2O. Et2C(CN)CO2H, in 31 g-yield from 42.5, g. of the ester and 28 g. KOH in 300 cc. MeOH, m. 61° (Hesse, Am.Chem. J. 18, 746(1896), gives 57°). Salts: silver, bulky precipitate; barium, needles; lead, flat flakes; calcium, needles with 3 H2O; strontium, prisms with 3 H2O; cadmium, flat plates with 3 H2O; copper, bright green rectangles with 3 H2O. From 50 g. NCCH2. CO2Et, in 100 cc. alc. and 10.2 g. Na in 250 cc. alc. treated with 80 g. PrI and allowed to stand overnight, is obtained 51.5 g. crude product (a), b24 117-30°; this is shaken in Et2O with 10% NaOH and the alk. extract acidified with dilute H2SO4 and extracted with Et2O, giving 24.9 g. α-cyanovaleric acid; silver and barium salts; Et ester, from the Ag salt and EtI, b755 218-9°, d32 0.972. The Et2O solution of (a), after extraction with NaOH, yields 17.8 g. of Et α-propyl-α-cyanovalerate, b22-3 129-32°, d26 0.93; free acid, rhombic prisms, m. 41°, becoming syrupy over H2SO4 in vacuo; after 5 days it contained 1 mol. H2O; silver salt, seps. with 1 H2O. In the same way from 50 g. NCCH2CO2Et are obtained 20.5 g. γ-methyl-α-cyanovaleric acid (silver salt, powder; barium salt, needles with 2 H2O; Et ester, b755 223-4°, d35 0.958), and 28. 1 g. Et γ-methyl-α-isobutyl-α-cyanovalerate, b755 245-50°, d31 0.915 (free acid, m. 82°; silver salt, bulky precipitate). Copper δ-methyl-α-cyanocaproate (cf. C. A. 7, 3506), blue crystalline precipitate with 7 H2O, turning green in vacuo over H2SO4; barium salt, needles with 2 H2O; chloride, liquid; anilide, needles, m. 102°. δ-Methyl-α-isoamyl-α-cyanocaproic acid, from the ester and KOH in MeOH,needles from C6H6, m. 74-5°; ammonium salt, flakes, 2.9 g. of which dissolve in 100 cc. H2O at 16°; silver salt, precipitate; copper salt, green flakes with 3 H2O; calcium salt, rhomboids with 4 H2O; amide, needles from alc., m. 152°. Lead benzylcyanoacetate, bulky crystalline precipitate with 3 H2O; calcium and barium salts, needles with 3 and 6 H2O; copper salt, deep blué precipitate with 5 H2O which it loses at 65°, turning green, m. 105-15° (decomposition); chloride, slightly colored liquid, does not distil under 35 mm. at a bath temperature of 290°. (PhCH2)2-(CN)CO2H, m. 194-5° (Cassirer, Ber. 25, 3027(1892), gives 188-9°); silver salt, precipitate; copper salt, blue precipitate with 1 H2O, turning green on drying. The Me ester, 6-sided plates from Et2O-ligroin, m. 78-9°, is obtained in 4.9 g. yield, together with 1.6 g. of the acid, when 20 g. NCCH2CO2Et in 125 cc. MeOH and 4.07 g. Na in 125 cc. MeOH are allowed to stand with 22 g. PhCH2Cl 14 h. and the fraction b15 195-260° of theproduct is shaken in Et2O with 10% NaOH.

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

Synthetic Route of C5H7NO2. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 2-Cyano-2-methylpropanoic acid, is researched, Molecular C5H7NO2, CAS is 22426-30-8, about Nitrilase-catalyzed selective hydrolysis of dinitriles and green access to the cyanocarboxylic acids of pharmaceutical importance. Author is Zhu, Dunming; Mukherjee, Chandrani; Biehl, Edward R.; Hua, Ling.

To further explore its synthetic applications, the nitrilase bll6402 from Bradyrhizobium japonicum strain USDA110 has been examined toward the hydrolysis of various dinitriles. It has been found that nitrilase bll6402 effectively hydrolyzed α,ω-dinitriles NCXCN [X = (CH2)n, n = 1-6, 8] to ω-cyanocarboxylic acids NCXCO2H, and the selectivity was independent of the substrate chain length. This feature is distinct from all the known nitrilases of various sources. Nitrilase bll6402 was thus applied to the synthesis of 1-cyanocycloalkaneacetic acids I [X = (CH2)n, n = 1, 2, 3], the useful precursors for the synthesis of gabapentin and its analogs.

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 2-Cyano-2-methylpropanoic acid, is researched, Molecular C5H7NO2, CAS is 22426-30-8, about Exploring the synthetic applicability of a cyanobacterium nitrilase as catalyst for nitrile hydrolysis.Recommanded Product: 2-Cyano-2-methylpropanoic acid.

The substrate specificity and synthetic applicability of the nitrilase from cyanobacterium Synechocystis sp. strain PCC 6803 have been examined This nitrilase catalyzed the hydrolysis of both aromatic and aliphatic nitriles to the corresponding acids in high yields. Furthermore, the stereoselective hydrolysis of phenyl-substituted β-hydroxy nitriles to (S)-enriched β-hydroxy carboxylic acids and selective hydrolysis of α,ω-dinitriles with five or less methylene groups to ω-cyano carboxylic acids have been achieved. This suggested that nitrilase from Synechocystis sp. PCC 6803 could be a useful enzyme catalyst for the “”green”” nitrile hydrolysis.

From this literature《Exploring the synthetic applicability of a cyanobacterium nitrilase as catalyst for nitrile hydrolysis》,we know some information about this compound(22426-30-8)Recommanded Product: 2-Cyano-2-methylpropanoic acid, but this is not all information, there are many literatures related to this compound(22426-30-8).

Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

Name: 2-Cyano-2-methylpropanoic acid. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 2-Cyano-2-methylpropanoic acid, is researched, Molecular C5H7NO2, CAS is 22426-30-8, about Development of Nonpeptidic Inverse Agonists of the Ghrelin Receptor (GHSR) Based on the 1,2,4-Triazole Scaffold. Author is Haj Salah, Khoubaib Ben; Maingot, Mathieu; Blayo, Anne-Laure; M’Kadmi, Celine; Damian, Marjorie; Mary, Sophie; Cantel, Sonia; Neasta, Jeremie; Oiry, Catherine; Peraldi-Roux, Sylvie; Fernandez, Gimena; Romero, Guadalupe Garcia; Perello, Mario; Marie, Jacky; Baneres, Jean-Louis; Fehrentz, Jean-Alain; Denoyelle, Severine.

GHSR controls, among others, growth hormone and insulin secretion, adiposity, feeding, and glucose metabolism Therefore, an inverse agonist ligand capable of selectively targeting GHSR and reducing its high constitutive activity appears to be a good candidate for the treatment of obesity-related metabolic diseases. In this context, we present a study that led to the development of several highly potent and selective inverse agonists of GHSR based on the 1,2,4-triazole scaffold. We demonstrate that, depending on the nature of the substituents on positions 3, 4, and 5, this scaffold leads to ligands that exert an intrinsic inverse agonist activity on GHSR-catalyzed G protein activation through the stabilization of a specific inactive receptor conformation. Thanks to an in vivo evaluation, we also show that one of the most promising ligands, compound I, not only exerts an effect on insulin secretion in rat pancreatic islets but also affects the orexigenic effects of ghrelin in mice.

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

Recio, Antonio; Tunge, Jon A. published an article about the compound: 2-Cyano-2-methylpropanoic acid( cas:22426-30-8,SMILESS:CC(C)(C#N)C(O)=O ).SDS of cas: 22426-30-8. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:22426-30-8) through the article.

Palladium-catalyzed decarboxylative α-allylation of nitriles readily occurs with use of Pd2(dba)3 and rac-BINAP. This catalyst mixture also allows the highly regiospecific α-allylation of nitriles in the presence of much more acidic α-protons. Thus, the reported method provides access to compounds that are not readily available via base-mediated allylation chemistries. Lastly, mechanistic investigations indicate that there is a competition between C- and N-allylation of an intermediate nitrile-stabilized anion and that N-allylation is followed by a rapid [3,3]-sigmatropic rearrangement.

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 22426-30-8, is researched, SMILESS is CC(C)(C#N)C(O)=O, Molecular C5H7NO2Journal, Article, Journal of Medicinal Chemistry called Peptidomimetic α-acyloxymethylketone warheads with six-membered lactam P1 glutamine mimic: SARS-CoV-2 3CL protease inhibition, coronavirus antiviral activity, and in vitro biological stability, Author is Bai, Bing; Belovodskiy, Alexandr; Hena, Mostofa; Kandadai, Appan Srinivas; Joyce, Michael A.; Saffran, Holly A.; Shields, Justin A.; Khan, Muhammad Bashir; Arutyunova, Elena; Lu, Jimmy; Bajwa, Sardeev K.; Hockman, Darren; Fischer, Conrad; Lamer, Tess; Vuong, Wayne; van Belkum, Marco J.; Gu, Zhengxian; Lin, Fusen; Du, Yanhua; Xu, Jia; Rahim, Mohammad; Young, Howard S.; Vederas, John C.; Tyrrell, D. Lorne; Lemieux, M. Joanne; Nieman, James A., the main research direction is peptidomimetic acyloxymethylketone warhead lactam glutamine mimic synthesis anticoronavirus agent; SARS CoV2 3CLpro protease inhibitor covalent adduct crystal structure.Formula: C5H7NO2.

Recurring coronavirus outbreaks, such as the current COVID-19 pandemic, establish a necessity to develop direct-acting antivirals that can be readily administered and are active against a broad spectrum of coronaviruses. Described in this Article are novel α-acyloxymethylketone warhead peptidomimetic compounds with a six-membered lactam glutamine mimic in P1. Compounds with potent SARS-CoV-2 3CL protease and in vitro viral replication inhibition were identified with low cytotoxicity and good plasma and glutathione stability. Compounds 15e, 15h, and 15l displayed selectivity for SARS-CoV-2 3CL protease over CatB and CatS and superior in vitro SARS-CoV-2 antiviral replication inhibition compared with the reported peptidomimetic inhibitors with other warheads. The cocrystn. of 15l with SARS-CoV-2 3CL protease confirmed the formation of a covalent adduct. α-Acyloxymethylketone compounds also exhibited antiviral activity against an alphacoronavirus and non-SARS betacoronavirus strains with similar potency and a better selectivity index than remdesivir. These findings demonstrate the potential of the substituted heteroaromatic and aliphatic α-acyloxymethylketone warheads as coronavirus inhibitors, and the described results provide a basis for further optimization.

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Journal of the American Chemical Society called Effect of structure on kinetics and mechanism of the alkaline hydrolysis of anilides, Author is Biechler, Sydney S.; Taft, Robert W. Jr., which mentions a compound: 22426-30-8, SMILESS is CC(C)(C#N)C(O)=O, Molecular C5H7NO2, Recommanded Product: 2-Cyano-2-methylpropanoic acid.

The rates of the aqueous alk. hydrolysis of CF3CONHPh (I) and a series of N-methylanilides, RCONMePh (II), were determined at 2.55° spectrophotometrically. I (3.5 g.) in 60 cc. dry Me2CO treated with 3.7 g. powd. KOH and 1.7 cc. MeI in 10 cc. dry Me2CO, refluxed 0.5 hr., and filtered, the filtrate evaporated, the residual oil diluted with H2O and extracted with Et2O, and the extract worked up gave MePhNCOCF3, m. 25-6°. PhNHMe, 6.4 g. HCO2H, and 20 cc. PhMe refluxed with the azeotropic removal of H2O and distilled gave MePhNCHO, b15 130°, n25D 1.552. PhNH2 (5 g.), a pinch of powd. KOH, and 4 g. CHF2CO2Et refluxed 2 days gave PhNHCOCHF2, m. 58° (aqueous EtOH). PhOCH2COCl (5 g.) in 25 cc. dry Et2O treated dropwise with MeNHPh until the reaction ceased and filtered, and the filtrate washed and worked up gave PhOCH2CONMePh, m. 92-3° (aqueous EtOH). In the same manner was prepared ClCH2CONMePh (III), m. 68-9° (aqueous EtOH). III (7.7 g.) and 10 cc. Me3N heated 3 hrs. in 20 cc. absolute EtOH and the resulting viscous liquid dried over refluxing xylene in a drying pistol gave betaine-N-methylanilide, hygroscopic solid. NCCH2CO2Et (20 g.) added to 10 g. Na in 100 g. absolute EtOH, the mixture treated with cooling with 50 cc. MeI in 20 cc. EtOH, refluxed 4 hrs., and evaporated, the residue diluted with H2O and extracted with Et2O, and the extract worked up gave NCCMe2CO2Et, b15 75°, n25D 1.4098; the ester saponified, the acid, m. 54-5°, converted to the acid chloride, b13 58°, and this dissolved in Et2O and treated dropwise with PhNHMe gave Me2C(CN)CONMePh, m. 55-6° (aqueous EtOH). I (0.328 g.) and 0.679M NaOH in aqueous dioxane kept 2 days and extracted with Et2O, and the extract dried and treated with dry HCl yielded 54.4% PhNH2.HCl; the aqueous layer treated with 10 cc. concentrated HCl and extracted with Et2O, the Et2O removed at 33°, and the residue titrated with NaOH showed 59.6% recovery of CF3CO2H. The rate constants, k1 × 103 min.-1 for the alk. hydrolysis of I in 50% aqueous dioxane at a constant ionic strength (0.500M) and in H2O at 25°, were determined at various concentrations of hydroxyl ion (M concentration of OH- given); the hydrolysis proceeded by 1st-order kinetics, and proceeded by the rate law k1 = k2(OH-)/1 + (OH-)K. The rate constants, k1 min.-1, for the II (R = CF3, CHF2, CH2Cl, CH2N+Me3, CMe2CN, CH2OPh, H) were determined in H2O at 25.5° in the presence and absence of Na2SO4 at varying hydroxyl ion and added salt concentrations The rate law followed by the II is k1 = k2(OH-) + k3(OH-)2. The ratio k3/k2 for the hydrolysis in H2O at 25.5° and an ionic strength of 0.6M was determined for the various II (R and ratio given): CF3 190, CHF2 34, CMe2CN 0.5, CH2OPh 0.7, H 3.4, CH2Cl 2.0, CH2N+Me3 5.6. The mechanism of the hydrolysis of I and II is discussed and correlated with the exptl. data.

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Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method