Month: January 2023

Synthesis, evaluation and structure-activity relationships of 5-alkyl-2,3-dihydroimidazo[1,2-c]quinazoline, 2,3-dihydroimidazo[1,2-c]quinazolin-5(6H)-thiones and their oxo-analogues as new potential bronchodilators was written by Bahekar, Rajesh H.;Rao, A. Raghu Ram. And the article was included in Arzneimittel-Forschung in 2001.Computed Properties of C7H4Br2N2 This article mentions the following:

With an aim to obtain potent bronchodilators, 2 series of 5-alkyl-2,3-dihydroimidazo[1,2-c]quinazolines (Va-1), 2,3-dihydroimidazo[1,2-c]quinazolin-5-(6H)-thiones (VIIIa-d) and their oxo-analogs (IXa-d) were designed. The compounds Va-1 were synthesized by two alternative routes. The former (Method A) based on the dehydrocyclization of 4-(1-hydroxyethyl)aminoquinazoline (IV) and the latter (Method B) involves the usage of 2-aminobenzonitrile (VI) which on reaction with ethylenediamine leads to the formation of the key intermediate 2-(2-aminophenyl)-4,5-dihydro-1H-imidazoles (VII). Finally the intermediate VII on condensation with different acid anhydrides yielded the title compound V. In general, method-A resulted the compound V in quantatively higher yields. 2,3-Dihydroimidazo[1,2-c]quinazolin-5 (6H)-thiones (VIII) were obtained by condensing VIi with carbon disulfide and a further oxidation of VIII gave their corresponding oxo-analogs (IX). The title compounds V, VIII and IX were evaluated for their bronchodilator activity using in vitro and in vivo (standard animal models) methods. All the test compounds exhibited bronchodilator activity. The structure activity relationship studies indicated good correlation between the nature of the substituent and bronchodilator activity. In the 5-alkyl substituted compounds V, a longer alkyl chain showed higher bronchodilator activity. Compounds VIII and IX were less potent and replacement of sulfur with oxygen showed no significant effect on the biol. activity. The presence of halogens altered the biol. activity in both the series. Among the compounds tested, 9-iodo-5-(propyl)-2,3-dihydroimidazo[1,2-c]quinazoline (VI) was the most potent (percentage protection = 87.1%; relative activity = 1.1 compared to the standard aminophylline). In the experiment, the researchers used many compounds, for example, 2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5Computed Properties of C7H4Br2N2).

2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5) 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. 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.Computed Properties of C7H4Br2N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Clickable Transformation of Nitriles (RCN) to Oxazolyl Sulfonyl Fluoride Warheads was written by Fang, Wan-Yin;Wang, Shi-Meng;Zhang, Zai-Wei;Qin, Hua-Li. And the article was included in Organic Letters in 2020.COA of Formula: C8H4F3NO This article mentions the following:

The protocol for simple, efficient, and mild synthesis of oxazolyl sulfonyl fluorides was developed through Rh₂(OAc)₄-catalyzed annulation of methyl-2-diazo-2-(fluorosulfonyl)acetate (MDF) or its Et ester derivative with nitriles. This practical method provides a general and direct route to a unique class of highly functionalized oxazolyl-decorated sulfonyl fluoride warheads with great potential in medicinal chem., chem. biol., and drug discovery. In the experiment, the researchers used many compounds, for example, 2-(Trifluoromethoxy)benzonitrile (cas: 63968-85-4COA of Formula: C8H4F3NO).

2-(Trifluoromethoxy)benzonitrile (cas: 63968-85-4) 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. 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.COA of Formula: C8H4F3NO

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Insight into and practical application of pH-controlled asymmetric transfer hydrogenation of aromatic ketones in water was written by Wu, Xiaofeng;Li, Xiaoguang;King, Frank;Xiao, Jianliang. And the article was included in Angewandte Chemie, International Edition in 2005.Application of 101219-69-6 This article mentions the following:

Much faster, more enantioselective, and more-productive catalysis was attained in the asym. transfer hydrogenation of aromatic ketones with the Noyori-Ikariya Ru-Ts-dpen catalyst in water under slightly basic conditions. At low pH values, the reaction was much less efficient and appears to operate through a different mechanism. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Application of 101219-69-6).

(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. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Application of 101219-69-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Cyclopropenone-Catalyzed Direct Conversion of Aldoximes and Primary Amides into Nitriles was written by Rai, Ankita;Yadav, Lal Dhar S.. And the article was included in European Journal of Organic Chemistry in 2013.Formula: C6H5NS This article mentions the following:

Efficient conversion of aldoximes and primary amides into nitriles by employing cyclopropenone as an organocatalyst is reported. The reaction proceeds smoothly under mild conditions with 5 mol-% catalyst loading to afford nitriles in excellent yields (78-94 %) in a single operation. This method is equally applicable to both aldoximes and primary amides bearing aromatic, heterocyclic, and aliphatic moieties. The convenient and catalytic procedure widens the scope of the utilization of cyclopropenones in organic synthesis. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Formula: C6H5NS).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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.Formula: C6H5NS

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Highly efficient amination in neat water of benzyl chlorides with dialkylformamides catalyzed by N-heterocyclic carbene-palladium(II)-1-methylimidazole complex was written by Chen, Wen-Xin;Zhang, Cai-Yun;Lu, Jian-Mei. And the article was included in Journal of Chemical Research in 2013.Safety of 4-(Morpholinomethyl)benzonitrile This article mentions the following:

N,N-dialkylbenzylamines were synthesized from substituted benzyl chlorides and dialkylformamides in good to almost quant. yields in a eco-friendly solvent, water, in the presence of NHC-Pd(II)-Im complex. In the experiment, the researchers used many compounds, for example, 4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4Safety of 4-(Morpholinomethyl)benzonitrile).

4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4) 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. 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.Safety of 4-(Morpholinomethyl)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Immobilization of chiral Rh catalyst on glass and application to asymmetric transfer hydrogenation of aryl ketones in aqueous media was written by Cheng, Tan-Yu;Zhuang, Jing-Lan;Yao, Hui;Zhang, Huai-Sheng;Liu, Guo-Hua. And the article was included in Chinese Chemical Letters in 2014.Reference of 101219-69-6 This article mentions the following:

A chiral catalyst, Cp^*RhTsDPEN (Cp^* = pentamethylcyclopentadiene, TsDPEN = substituted N-phenylsulfonyl-1,2-diphenylethylenediamine), was synthesized and immobilized at the surface of glass. The immobilized catalyst exhibited good catalytic efficiency for asym. transfer hydrogenation of aromatic ketones in water with HCO₂Na as hydrogen source. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Reference of 101219-69-6).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Structure-activity relationships for 2-anilino-6-phenylpyrido[2,3-d]pyrimidin-7(8H)-ones as inhibitors of the cellular checkpoint kinase Wee1 was written by Palmer, Brian D.;Smaill, Jeff B.;Rewcastle, Gordon W.;Dobrusin, Ellen M.;Kraker, Alan;Moore, Charles W.;Steinkampf, Randall W.;Denny, William A.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2005.Safety of 2-(2,6-Dibromophenyl)acetonitrile This article mentions the following:

A series of 2-anilino-6-phenylpyrido[2,3-d]pyrimidin-7(8H)-ones, e.g., I, were synthesized and evaluated for their inhibitory properties against the non-receptor kinase c-Src and the G2/M checkpoint kinase Wee1. Overall, the compounds were 10-100-fold more potent inhibitors of c-Src than Wee1, and variation of substituents on the 6-Ph ring did not markedly alter this preference. Solubilizing substituents off the 2-anilino ring in many cases increased Wee1 activity, thus lowering this preference to about 10-fold. 5-Alkyl substituted analogs were generally Wee1 selective, but at the expense of absolute potency. In the experiment, the researchers used many compounds, for example, 2-(2,6-Dibromophenyl)acetonitrile (cas: 67197-53-9Safety of 2-(2,6-Dibromophenyl)acetonitrile).

2-(2,6-Dibromophenyl)acetonitrile (cas: 67197-53-9) 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.Safety of 2-(2,6-Dibromophenyl)acetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Pyridinylpyrimidines selectively inhibit human methionine aminopeptidase-1 was written by Zhang, Pengtao;Yang, Xinye;Zhang, Feiran;Gabelli, Sandra B.;Wang, Renxiao;Zhang, Yihua;Bhat, Shridhar;Chen, Xiaochun;Furlani, Manuel;Amzel, L. Mario;Liu, Jun O.;Ma, Dawei. And the article was included in Bioorganic & Medicinal Chemistry in 2013.Recommanded Product: 4-methoxypicolinonitrile This article mentions the following:

Cellular protein synthesis is initiated with methionine in eukaryotes with few exceptions. Methionine aminopeptidases (MetAPs) which catalyze the process of N-terminal methionine excision are essential for all organisms. In mammals, type 2 MetAP (MetAP2) is known to be important for angiogenesis, while type 1 MetAP (MetAP1) has been shown to play a pivotal role in cell proliferation. Authors’ previous high-throughput screening of a com. compound library uncovered a novel class of inhibitors for both human MetAP1 (HsMetAP1) and human MetAP2 (HsMetAP2). This class of inhibitors contains a pyridinylpyrimidine core. To understand the structure-activity relationship (SAR) and to search for analogs of 2 with greater potency and higher HsMetAP1-selectivity, a total of 58 analogs were acquired through either com. source or by inhouse synthesis and their inhibitory activities against HsMetAP1 and HsMetAP2 were determined Through this systematic medicinal chem. anal., the authors have identified: (1) 5-chloro-6-methyl-2-pyridin-2-ylpyrimidine as the min. element for the inhibition of HsMetAP1; (2) 5′-chloro as the favored substituent on the pyridine ring for the enhanced potency against HsMetAP1; and (3) long C4 side chains as the essentials for higher HsMetAP1-selectivity. As a result of the SAR campaign, six compounds were found to be among the most selective and potent inhibitors of purified HsMetAP1 reported to date. In addition, crystallog. anal. of one representative inhibitor (I) in complex with N-terminally truncated HsMetAP1 was also performed. Map gene. In the experiment, the researchers used many compounds, for example, 4-methoxypicolinonitrile (cas: 36057-44-0Recommanded Product: 4-methoxypicolinonitrile).

4-methoxypicolinonitrile (cas: 36057-44-0) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 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: 4-methoxypicolinonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Bifunctional design of stable metal-organic framework bearing triazole-carboxylate mixed ligand: Highly efficient heterogeneous catalyst for knoevenagel condensation reaction under mild conditions was written by Liu, Feixiong;Kumar, Sandeep;Li, Shuangshuang;You, Hengzhi;Ren, Peng;Zhao, Limin. And the article was included in Catalysis Communications in 2020.Recommanded Product: 55490-87-4 This article mentions the following:

A highly water stable zinc metal-organic framework (ZnMOF), {[Zn(HL)₂]}_n, was synthesized using a triazole-carboxylate-based mixed ligand (L = 5-(4H-1,2,4-triazol-4-yl)isophthalic acid). A 2D MOF was formed by hydrothermal synthesis, and extended to a 3D supramol. network through strong hydrogen bonding. This MOF was fully characterized by Fourier-transformation IR spectroscopy, thermogravimetric anal., single-crystal X-ray diffraction (XRD), powder XRD and elemental anal. Owing to the d10 configuration of this ZnMOF, its luminescent properties were suitable for the sensing of the CN^– ions over other anions, as inferred from the florescence result. However, regarding the catalytic mechanism, this ZnMOF showed a strong ability to react with CN^–, which might be due to the hydrogen bonding between the COOH groups without coordination. This interaction behavior with CN^– ions makes the ZnMOF a promising heterogeneous catalyst for Knoevenagel condensations using malononitrile and aldehyde derivatives as reactants under mild conditions. All reactions were conducted in water as a green solvent. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Recommanded Product: 55490-87-4).

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. 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.Recommanded Product: 55490-87-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis and Characterization of Amidato Divalent Lanthanide Complexes and Their Use in Forming 2,4-Quinazolidinones from CO₂ and 2-Aminobenzonitriles was written by Wang, Qianyu;Lu, Chengrong;Zhao, Bei;Yao, Yingming. And the article was included in European Journal of Organic Chemistry in 2016.Application In Synthesis of 2-Amino-3-chlorobenzonitrile This article mentions the following:

Four amidato divalent lanthanide complexes, {LⁿLn[N(TMS)₂]THF}₂ [n = 1, Ln = Eu (I); n = 2, Ln = Eu (III), Yb (IV); HL¹ = tBuC₆H₄CONHC₆H₃(iPr)₂; HL² = C₆H₅CONHC₆H₃(iPr)₂] and {L³Eu[N(TMS)₂]THF}{L³₂Eu(THF)₂} (II) [HL³ = ClC₆H₄CONHC₆H₃(iPr)₂], were synthesized and extensively characterized. This is the first time that the amidato lanthanide amides I–IV were used to catalyze the reactions of CO₂ and 2-aminobenzonitriles to form quinazoline-2,4(1H,3H)-diones at atm. pressure. All the complexes efficiently catalyzed the transformation, with complex III showing the highest activity. This catalytic system gave good to excellent yields, and good functional group tolerance. Preliminary studies were conducted to investigate the reaction mechanism. In the experiment, the researchers used many compounds, for example, 2-Amino-3-chlorobenzonitrile (cas: 53312-77-9Application In Synthesis of 2-Amino-3-chlorobenzonitrile).

2-Amino-3-chlorobenzonitrile (cas: 53312-77-9) 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. 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.Application In Synthesis of 2-Amino-3-chlorobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts