Month: February 2023

De novo synthesis of bifunctional conjugated microporous polymers for synergistic coordination mediated uranium entrapment was written by Yu, Boxuan;Zhang, Lei;Ye, Gang;Liu, Qingzhi;Li, Jiongli;Wang, Xudong;Chen, Jing;Xu, Shengming;Ma, Shengqian. And the article was included in Nano Research in 2021.Formula: C7H4Br2N2 This article mentions the following:

This work reports a de novo synthesis of novel bifunctional conjugated microporous polymers (CMPs) exhibiting a synergistic-effect involved coordination behavior to uranium. It is highlighted that the synthetic strategy enables the engineering of the coordination environment within amidoxime functionalized CMP frameworks by specifically introducing ortho-substituted amino functionalities, enhancing the affinity to uranyl ions via forming synergistic complexes. The CMPs exhibit high Brunauer-Emmett-Teller (BET) surface area, well-developed three-dimensional (3D) networks with hierarchical porosity, and favorable chem. and thermal stability because of the covalently cross-linked structure. Compared with the amino-free counterparts, the adsorption capacity of bifunctional CMPs was increased by almost 70%, from 105 to 174 mg/g, indicating evidently enhanced binding ability to uranium. Moreover, new insights into coordination mechanism were obtained by in-depth XPS anal. and d. functional theory (DFT) calculation, suggesting a dominant role of the oxime ligands forming a 1:1 metal ions/ligands (M/L) coordination model with uranyl ions while demonstrating the synergistic engagement of the amino functionalities via direct binding to uranium center and hydrogen-bonding involved secondary-sphere interaction. This work sheds light on the underlying principles of ortho-substituted functionalities directed synergistic effect to promote the coordination of amidoxime with uranyl ions. And the synthetic strategy established here would enable the task-specific development of more novel CMP-based functional materials for broadened applications. In the experiment, the researchers used many compounds, for example, 2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5Formula: C7H4Br2N2).

2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5) 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. Formula: C7H4Br2N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Solar thermochemical reactions. Part II. Synthesis of 2-aminothiophenes via Gewald reaction induced by solar thermal energy was written by Mekheimer, Ramadan Ahmed;Ameen, Mohamed Abdallah;Sadek, Kamal Usef. And the article was included in Chinese Chemical Letters in 2008.Name: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile This article mentions the following:

Green conditions were developed for the synthesis of substituted 2-aminothiophenes employing multicomponent reactions of a ketone with active methylene nitrile and elemental sulfur induced by free solar thermal energy. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Name: 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. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. 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.Name: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electrospinning NH₂-MIL-101/PAN nanofiber mats: A promising catalyst with Lewis acidic and basic bifunctional sites for organic transformation reactions was written by Hassan, Hassan M. A.;Alhumaimess, Mosaed S.;Kamel, Mahmoud M.;Alsohaimi, Ibrahim H.;Aljaddua, Huda I.;Aldosari, Obaid F.;Algamdi, Mohammad. S.;Mohamed, Rasha M. K.;El-Aassar, M. R.. And the article was included in Colloids and Surfaces, A: Physicochemical and Engineering Aspects in 2022.Safety of 2-(Anthracen-9-ylmethylene)malononitrile This article mentions the following:

Because of their distinctive characteristics, like great surface area and capability of structure modifications, Metal-organic frameworks (MOFs) were endorsed as outstanding candidates for catalysis purposes. The incorporation of MOF into an organic polymer frameworks is thought to be a promising approach to enhance the catalysts performance, however, a facile and low-cost approach to prepare such catalysts is currently missing. Herein, a direct approach for integration the MOF into nanofibers with improved catalytic organic transformation reactions without film rupture is reported. The electrospun NH₂-MIL-101 @polyacrylonitrile (PAN) catalyst nanofibers with varied MOF to PAN mass ratio was fabricated by a facile electrospinning approach and used as integrated catalyst for Friedel-Crafts acylation of anisole, esterification of amyl alc., and Knoveonagel condensation reaction of aldehydes. The fabricated MOF-catalysts nanofibers NH₂-MIL-101 @PAN show effective anisole acylation, ester production, and Knoveonagel condensation reaction. The anisole acylation, ester production, and Knoveonagel condensation efficiency boosted to 90%, 79%, and 98% after incorporating NH₂-MIL-101 nanocrystals into the elctrospun PAN nanofibers. The great surface area, available active centers in the pore architecture, and unsaturated Cr³⁺ Lewis acid centers are responsible for this exceptional performance. Because of its adaptability, our approach offers a cutting-edge and intriguing platform for the future tailoring of MOF fabrics with a wide range of practical uses. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Safety of 2-(Anthracen-9-ylmethylene)malononitrile).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Industrially, the main methods for producing nitriles are ammoxidation and hydrocyanation. Both routes are green in the sense that they do not generate stoichiometric amounts of salts.Safety of 2-(Anthracen-9-ylmethylene)malononitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

One-Pot Preparation of C₁-Homologated Aliphatic Nitriles from Aldehydes through a Wittig Reaction under Metal-Cyanide-Free Conditions was written by Ezawa, Masatoshi;Togo, Hideo. And the article was included in European Journal of Organic Chemistry in 2017.Synthetic Route of C8H13N This article mentions the following:

A one-pot protocol to obtain C₁-homologated aliphatic nitriles was achieved by treating aromatic and aliphatic aldehydes with the (methoxymethyl)triphenylphosphonium ylide followed by hydrolysis of the resulting Me vinyl ethers with pTsOH (Ts = para-toluenesulfonyl) and treatment with mol. iodine and aqueous ammonia under metal cyanide free conditions. Neopentyl-type nitriles, which could not be obtained by conventional methods that involved conversion of the neopentyl alc. into a tosylate and treatment with metal cyanide, were successfully obtained by using the present method. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Synthetic Route of C8H13N).

2-Cyclohexylacetonitrile (cas: 4435-14-7) 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. 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.Synthetic Route of C8H13N

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Discovery of Tetrasubstituted Imidazolines as Potent and Selective Neuropeptide Y Y5 Receptor Antagonists: Reduced Human Ether-a-go-go Related Gene Potassium Channel Binding Affinity and Potent Antiobesity Effect was written by Sato, Nagaaki;Ando, Makoto;Ishikawa, Shiho;Jitsuoka, Makoto;Nagai, Keita;Takahashi, Hirobumi;Sakuraba, Aya;Tsuge, Hiroyasu;Kitazawa, Hidefumi;Iwaasa, Hisashi;Mashiko, Satoshi;Gomori, Akira;Moriya, Ryuichi;Fujino, Naoko;Ohe, Tomoyuki;Ishihara, Akane;Kanatani, Akio;Fukami, Takehiro. And the article was included in Journal of Medicinal Chemistry in 2009.Name: 4-methoxypicolinonitrile This article mentions the following:

A series of novel imidazoline derivatives was synthesized and evaluated as neuropeptide Y (NPY) Y5 receptor antagonists. Optimization of previously reported imidazoline leads, I and II, was attempted by introduction of substituents at the 5-position on the imidazoline ring and modification of the bis(4-fluorophenyl) moiety. A number of potent derivatives without human ether-a-go-go related gene potassium channel (hERG) activity were identified. Selected compounds, including III, were shown to have excellent brain and CSF permeability. Compound III displayed a suitable pharmacokinetic profile for chronic in vivo studies and potently inhibited D-Trp³⁴NPY-induced acute food intake in rats. Oral administration of III resulted in a potent reduction of body weight in a diet-induced obese mouse model. In the experiment, the researchers used many compounds, for example, 4-methoxypicolinonitrile (cas: 36057-44-0Name: 4-methoxypicolinonitrile).

4-methoxypicolinonitrile (cas: 36057-44-0) 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 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.Name: 4-methoxypicolinonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Highly selective chemodosimeter for cyanide based on a doubly activated Michael acceptor type of coumarin thiazole fluorophore was written by Park, Seokan;Kim, Hae-Jo. And the article was included in Sensors and Actuators, B: Chemical in 2012.Recommanded Product: 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile This article mentions the following:

A doubly activated Michael acceptor type of coumarin thiazole fluorophore (1) was prepared and applied for the detection of cyanide ions in aqueous solution The chemodosimeter exhibited a highly selective and sensitive response to cyanide over other various anions through the Michael addition of cyanide to 1. Upon the addition of cyanide ions, the apparent color and fluorescence changes of 1 were observable with a detection limit of 2.3 μM of the cyanide anions in aqueous solution In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Recommanded Product: 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile).

7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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: 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The biological action of malononitriles. I. The effect of substituted malononitriles on the growth of transplanted tumors in mice was written by Gal, Emery M.;Fung, Fung-Haan;Greenberg, David M.. And the article was included in Cancer Research in 1952.Category: nitriles-buliding-blocks This article mentions the following:

The following compounds were prepared and tested for toxicity and effect on sarcoma, carcinoma, and myeloid leukemia in mice; compounds marked *inhibited tumor growth, || slightly promoted tumor growth, † were first synthesized here, ‡ irritated skin and mucous membranes, in each case the substituent on the methylene group of malononitrile is given: 2-(methoxycarboxy)ethyl-, 2-(ethoxycarboxy)ethyl-, 2-cyanoethyl-, methylenebis-, ethylidenebis-, heptylidenebis-, ethoxymethylene- *, aminomethylene-, glyceral- †, citral- †, tiglal- †, furfurylidene-, 5-nitrofurfurylidene- *‡, 2-thenylidene-, 5-nitro-2-thenylidene-, benzylidene- *‡, o-hydroxybenzylidene-, m-hydroxybenzylidene-, p-hydroxybenzylidene- *‡, 2,4-dihydroxybenzylidene-, 3,5-dihydroxybenzylidene-, o-methylbenzylidene- ‡, m-methylbenzylidene-, p-methylbenzylidene-, o-chlorobenzylidene- ‡, p-chlorobenzylidene- *, 2-hydroxy-5-chlorobenzylidene-, 2,4-dichlorobenzylidene-, 2,6-dichlorobenzylidene-, o-nitrobenzylidene- ‡, m-nitrobenzylidene-, p-nitrobenzylidene- *, 2,4-dinitrobenzylidene-, 2,6-dinitrobenzylidene-, 2-chloro-5-nitrobenzylidene ‡, p-methoxybenzylidene-, 2,4-dimethoxybenzylidene-, 2,5-dimethoxybenzylidene-, 3,4-dimethoxybenzylidene-, 3,4,5-trihydroxybenzylidene- †, 3,4,5-trimethoxybenzylidene- †, 3-methoxy-4-hydroxybenzylidene-, piperonal- *, cinnamal-, p-acetamidobenzylidene-, p-dimethylaminobenzylidene-, p-diethylaminobenzylidene-, 1-ethoxy-2-naphthylmethylene-, 9-anthral-, cinchoninal-, α-methylbenzylidene-, 1-methyl-2-(p-chlorophenyl)ethylidene-, 1-methyl-2-cyclopropylethylidene-, 1-methyl-2-(p-fluorophenyl)ethylidene-, 1-methyl-2-(p-methylphenyl)ethylidene-, 1-methyl-2-(p-nitrophenyl)ethylidene- *, 1-propyl-2-phenylethylidene-, 1-methyl-2-furylethylidene- *, 1-methyl-2-thienylethylidene-, isatylphenylazo- ||, p-dimethylaminophenylazo- †||, p-nitrophenylazo- ||, and p-chlorophenylazo- ||. Tested were also 1,3-dimethyl-2,2,4,4-cyclobutanetetranitrile, 2-cyano-1,4-endomethylene-4-cyclohexene ‡, and fumaronitrile. The effects were attributed to the structural properties of the particular compounds rather than to release of cyanide at different rates. Neither NaCN nor malononitrile retarded any of the tumors tested. Toxicity symptoms of the substituted malononitriles were much the same as those described for the parent compound by Heymans and Masoin (Arch. pharmacodynamie 3, 77(1897)). In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Category: nitriles-buliding-blocks).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. 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.Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Discovery, Optimization, and in Vivo Evaluation of Benzimidazole Derivatives AM-8508 and AM-9635 as Potent and Selective PI3Kδ Inhibitors was written by Shin, Youngsook;Suchomel, Julia;Cardozo, Mario;Duquette, Jason;He, Xiao;Henne, Kirk;Hu, Yi-Ling;Kelly, Ron C.;McCarter, John;McGee, Lawrence R.;Medina, Julio C.;Metz, Daniela;San Miguel, Tisha;Mohn, Deanna;Tran, Thuy;Vissinga, Christine;Wong, Simon;Wannberg, Sharon;Whittington, Douglas A.;Whoriskey, John;Yu, Gang;Zalameda, Leeanne;Zhang, Xuxia;Cushing, Timothy D.. And the article was included in Journal of Medicinal Chemistry in 2016.COA of Formula: C5H3ClN4 This article mentions the following:

Lead optimization efforts resulted in the discovery of two potent, selective, and orally bioavailable PI3Kδ inhibitors, 1 (AM-8508) and 2 (AM-9635), with good pharmacokinetic properties. The compounds inhibit B cell receptor (BCR)-mediated AKT phosphorylation (pAKT) in PI3Kδ-dependent in vitro cell based assays. These compounds which share a benzimidazole bicycle are effective when administered in vivo at unbound concentrations consistent with their in vitro cell potency as a consequence of improved unbound drug concentration with lower unbound clearance. Furthermore, the compounds demonstrated efficacy in a Keyhole Limpet Hemocyanin (KLH) study in rats, where the blockade of PI3Kδ activity by inhibitors 1 and 2 led to effective inhibition of antigen-specific IgG and IgM formation after immunization with KLH. In the experiment, the researchers used many compounds, for example, 4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4COA of Formula: C5H3ClN4).

4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4) 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.COA of Formula: C5H3ClN4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis and antimicrobial evaluation of new 4-{[(aryl)methylene]amino}-2-methyl-5,6-substituted thieno[2,3-d]pyrimidines was written by Naresh, K.;Rajeshwar, Y.;Jayaveera, K. N.. And the article was included in World Journal of Pharmacy and Pharmaceutical Sciences in 2014.Application of 70291-62-2 This article mentions the following:

A new series of 4-{[(aryl)methylene]amino}-2-methyl-5,6-substituted thieno[2,3-d]pyrimidines I (R₁R₂ = (CH₂)₃, (CH₂)₅; Ar = C₆H₅, 4-ClC₆H₄, 4-BrC₆H₄, 3-indolyl, etc.) was synthesized by the condensation of 4-amino-2,5,6-substituted theino[2,3-d]pyrimidines II with nine aromatic aldehydes. The compounds were further evaluated for the antibacterial and antifungal activity employing disk diffusion method. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Application of 70291-62-2).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) 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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Application of 70291-62-2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Convenient synthesis of disubstituted tacrine derivatives via electrophilic and copper induced reactions was written by Ekiz, Makbule;Tutar, Ahmet;Okten, Salih. And the article was included in Tetrahedron in 2016.Application of 68385-95-5 This article mentions the following:

The bromination of 2-aminobenzonitrile with mol. bromine (2 equiv) furnished 2-amino-3,5-dibromobenzonitrile in 98% yield. One-pot syntheses are described for dibromotacrine derivatives, e.g., I (Y = CH₂), utilizing Friedlander reactions. A convenient route is described for disubstituted derivatives of tacrines from dibromotacrine I (Y = CH₂, CH₂CH₂) (II) by various substitution reactions. Several disubstituted tacrines were synthesized by treatment of II with n-BuLi followed by trapping with an electrophile [Si(Me)₃Cl, S₂(Me)₂]. Both were converted to the corresponding cyano derivatives III (X = Br, Y = CH₂; X = CN, Y = CH₂; X = CN, CH₂CH₂) via copper-assisted nucleophilic substitution reactions in moderate yields (30%, 50%, and 60%, resp.). Copper-induced nucleophilic substitution of dibromide II (Y = CH₂CH₂) with NaOMe afforded mono-methoxide IV in 25% yield. In the experiment, the researchers used many compounds, for example, 2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5Application of 68385-95-5).

2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5) 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. 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.Application of 68385-95-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts