Category: nitriles-buliding-blocks

Bec, Anja; Hok, Lucija; Persoons, Leentje; Vanstreels, Els; Daelemans, Dirk; Vianello, Robert; Hranjec, Marijana published an article in 2021, the title of the article was Synthesis, Computational Analysis, and Antiproliferative Activity of Novel Benzimidazole Acrylonitriles as Tubulin Polymerization Inhibitors: Part 2.Reference of 3-Chloro-4-nitrobenzonitrile And the article contains the following content:

Classical linear and microwave-assisted synthesis methods was used to prepare novel N-substituted, benzimidazole-derived acrylonitriles I [R1 = H, cyano; R2 = Me, iso-Bu, Ph, etc.; R3 = H, 2-methoxy, 3,4,5-trimethoxy, etc.] with antiproliferative activity against several cancer cells in vitro. The most potent systems showed pronounced activity against all tested hematol. cancer cell lines, with favorable selectivity towards normal cells. The selection of lead compounds was also tested in vitro for tubulin polymerization inhibition as a possible mechanism of biol. action. A combination of docking and mol. dynamics simulations confirmed the suitability of the employed organic skeleton for the design of antitumor drugs and demonstrated that their biol. activity relies on binding to the colchicine binding site in tubulin. In addition, it also underlined that higher tubulin affinities are linked with (i) bulkier alkyl and aryl moieties on the benzimidazole nitrogen and (ii) electron-donating substituents on the Ph group that allow deeper entrance into the hydrophobic pocket within the tubulin’s β-subunit, consisting of Leu255, Leu248, Met259, Ala354, and Ile378 residues. The experimental process involved the reaction of 3-Chloro-4-nitrobenzonitrile(cas: 34662-29-8).Reference of 3-Chloro-4-nitrobenzonitrile

The Article related to phenylacrylonitrile benzimidazole preparation diastereoselective antitumor sar apoptosis mol docking, acrylonitriles, antiproliferative activity, benzimidazoles, docking analysis, molecular dynamics simulations, tubulin polymerization and other aspects.Reference of 3-Chloro-4-nitrobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

On March 31, 1991, Cristalli, Gloria; Eleuteri, Alessandra; Franchetti, Palmarisa; Grifantini, Mario; Vittori, Sauro; Lupidi, Giulio published an article.Category: nitriles-buliding-blocks The title of the article was Adenosine deaminase inhibitors: synthesis and structure activity relationships of imidazole analogs of erythro-9-(2-hydroxy-3-nonyl)adenine. And the article contained the following:

A series of erythro-1-(2-hydroxy-3-nonyl)imidazole derivatives were synthesized and evaluated for adenosine deaminase (ADA) inhibitory activity, in order to introduce simplifications in the ADA inhibitors erythro-9-(2-hydroxy-3-nonyl)adenine [EHNA, (I; X = N)] and 3-deaza-I (X = CH). Opening the pyrimidine or pyridine ring of I (X = N, CH), resp. led to compounds which are still ADA inhibitors. The most potent compound was erythro-1-(2-hydroxy-3-nonyl)imidazole-4-carboxamide (II; Ki = 3.53 × 10-8 M), which provided potential donor and acceptor sites for hydrogen bonding. Lack of one of this sites could account for the order of potency of all compounds examined in this series. Opening the same ring in adenosine and in 3-deazaadenosine led to fully inactive compounds These results support the hypothesis of the existence, at or near the enzyme active site, of a hydrophobic region able to bind the erythro-nonyl moiety. The experimental process involved the reaction of 2-Aminomalononitrile 4-methylbenzenesulfonate(cas: 5098-14-6).Category: nitriles-buliding-blocks

The Article related to adenosine deaminase inhibitor, erythrohydroxynonyladenine analog, structure activity relationship erythrohydroxynonylimidazole, adenine erythrohydroxylnonyl analog, imidazole erythrohydroxynonyl structure activity relationship and other aspects.Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

On November 20, 2008, Ohlmeyer, Michael J.; Bohnstedt, Adolph C.; Kingsbury, Celia; Ho, Koc-Kan; Quintero, Jorge Gabriel; You, Ming; Park, Haengsoon; Lu, Yingchun published a patent.Synthetic Route of 138801-92-0 The title of the patent was Preparation of purinones and imidazopyridinones as JAK3 kinase inhibitors useful as immunosuppressants. And the patent contained the following:

Title compounds e.g. [I; Q = CX1, N; X1 = H, cyano, halo, haloalkyl haloalkoxy; R4 = (substituted) aryl], were prepared Thus, (R)-4-(2,4-dimethoxybenzylamino)-3-[4-(6-fluorochroman-4-ylamino)-5-nitropyrimidin-2-ylamino]benzonitrile was stirred with Na2S2O4 and NaHCO3 in THF/H2O/MeOH to give (R)-4-(2,4-dimethoxybenzylamino)-3-[4-(6-fluorochroman-4-ylamino)-5-aminopyrimidin-2-ylamino]benzonitrile. The latter was microwaved with p-TsOH and (MeO)3CH in MeOH at 150° for 5 min. to give 3-[9-((R)-6-fluorochroman-4-yl)-9H-purin-2-yl]-3H-benzo[d]imidazole-5-carbonitrile. The latter and other title compounds showed JAK3 inhibitory activity with IC50 <100 nM. The experimental process involved the reaction of 4-Oxochroman-6-carbonitrile(cas: 138801-92-0).Synthetic Route of 138801-92-0

The Article related to purinone imidazopyridinone preparation jak3 kinase inhibitor, cancer inflammation psoriasis transplant rejection psoriasis treatment purinone preparation, chromanylpurinylbenzimidazole preparation autoimmune disease treatment and other aspects.Synthetic Route of 138801-92-0

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Zhu, Xing-Li; He, Wu-Jun; Yu, Liang-Liang; Cai, Chang-Wu; Zuo, Zong-Le; Qin, Da-Bin; Liu, Quan-Zhong; Jing, Lin-Hai published an article in 2012, the title of the article was Organocatalytic asymmetric vinylogous Michael addition of dicyanoolefins to imine intermediates generated in situ from arenesulfonylalkylindoles.Synthetic Route of 2510-01-2 And the article contains the following content:

An organocatalytic asym. vinylogous Michael addition of dicyanoolefins to vinylogous imine intermediates generated in situ from arenesulfonylalkylindoles has been developed. This protocol provides an easy and convenient approach to C-3 alkyl-substituted indole derivatives with high yields (up to 93%), diastereomeric ratios (up to 99:1 dr) and enantioselectivities (up to 99% ee). The resulting adducts can be also readily converted to pyrazolo derivatives or α-alkylation products of ketones without any decrease of the diastereoselectivities and enantioselectivities. The experimental process involved the reaction of 2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile(cas: 2510-01-2).Synthetic Route of 2510-01-2

The Article related to arenesulfonylalkylindole imine organocatalytic asym vinylogous michael addition dicyanoolefin, alkyl indole derivative enantioselective diastereoselective synthesis alkylation ketone pyrazole, michael adduct crystal structure and other aspects.Synthetic Route of 2510-01-2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

On March 31, 2020, Silva, Daniel; Mendes, Eduarda; Summers, Eleanor J.; Neca, Ana; Jacinto, Ana C.; Reis, Telma; Agostinho, Paula; Bolea, Irene; Jimeno, M. Luisa; Mateus, M. Luisa; Oliveira-Campos, Ana M. F.; Unzeta, Mercedes; Marco-Contelles, Jose; Majekova, Magdalena; Ramsay, Rona R.; Carreiras, M. Carmo published an article.Computed Properties of 75629-62-8 The title of the article was Synthesis, biological evaluation, and molecular modeling of nitrile-containing compounds: Exploring multiple activities as anti-Alzheimer agents. And the article contained the following:

Based on the monoamine oxidase (MAO) inhibition properties of aminoheterocycles with a carbonitrile group we have carried out a systematic exploration to discover new classes of carbonitriles endowed with dual MAO and AChE inhibitory activities, and Aβ anti-aggregating properties. Eighty-three nitrile-containing compounds, 13 of which are new, were synthesized and evaluated. In vitro screening revealed that 31, a new compound, presented the best lead for trifunctional inhibition against MAO A (0.34μM), MAO B (0.26μM), and AChE (52μM), while 32 exhibited a lead for selective MAO A (0.12μM) inhibition coupled to AChE (48μM) inhibition. Computational anal. revealed that the malononitrile group can find an advantageous position with the aromatic cleft and FAD of MAO A or MAO B. However, the total binding energy can be handicapped by an internal penalty caused by twisting of the ligand mol. and subsequent disruption of the conjugation (32 in MAO B compared to the conjugated 31). Conjugation is also important for AChE as well as the hydrophilic character of malononitrile that allows this group to be in close contact with the aqueous environment as seen for 83. Although the effect of 31 and 32 against Aβ1-42, was very weak, the effect of 63 and 65, and of the new compound 75, indicated that these compounds were able to disaggregate Aβ1-42 fibrils. The most effective was 63, a (phenylhydrazinylidene)propanedinitrile derivative that also inhibited MAO A (1.65μM), making it a potential lead for Alzheimer’s disease application. The experimental process involved the reaction of 2-((1H-Indol-3-yl)methylene)malononitrile(cas: 75629-62-8).Computed Properties of 75629-62-8

The Article related to nitrile compound acetylcholinesterase monoamine oxidase alzheimer agent biol evaluation, ache inhibitors, alzheimer’s disease, aβ1-42 disaggregating agents, mao inhibitors, in silico study, nitrile-containing compounds and other aspects.Computed Properties of 75629-62-8

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

On March 31, 2020, Silva, Daniel; Mendes, Eduarda; Summers, Eleanor J.; Neca, Ana; Jacinto, Ana C.; Reis, Telma; Agostinho, Paula; Bolea, Irene; Jimeno, M. Luisa; Mateus, M. Luisa; Oliveira-Campos, Ana M. F.; Unzeta, Mercedes; Marco-Contelles, Jose; Majekova, Magdalena; Ramsay, Rona R.; Carreiras, M. Carmo published an article.Formula: C10H11N3O3S The title of the article was Synthesis, biological evaluation, and molecular modeling of nitrile-containing compounds: Exploring multiple activities as anti-Alzheimer agents. And the article contained the following:

Based on the monoamine oxidase (MAO) inhibition properties of aminoheterocycles with a carbonitrile group we have carried out a systematic exploration to discover new classes of carbonitriles endowed with dual MAO and AChE inhibitory activities, and Aβ anti-aggregating properties. Eighty-three nitrile-containing compounds, 13 of which are new, were synthesized and evaluated. In vitro screening revealed that 31, a new compound, presented the best lead for trifunctional inhibition against MAO A (0.34μM), MAO B (0.26μM), and AChE (52μM), while 32 exhibited a lead for selective MAO A (0.12μM) inhibition coupled to AChE (48μM) inhibition. Computational anal. revealed that the malononitrile group can find an advantageous position with the aromatic cleft and FAD of MAO A or MAO B. However, the total binding energy can be handicapped by an internal penalty caused by twisting of the ligand mol. and subsequent disruption of the conjugation (32 in MAO B compared to the conjugated 31). Conjugation is also important for AChE as well as the hydrophilic character of malononitrile that allows this group to be in close contact with the aqueous environment as seen for 83. Although the effect of 31 and 32 against Aβ1-42, was very weak, the effect of 63 and 65, and of the new compound 75, indicated that these compounds were able to disaggregate Aβ1-42 fibrils. The most effective was 63, a (phenylhydrazinylidene)propanedinitrile derivative that also inhibited MAO A (1.65μM), making it a potential lead for Alzheimer’s disease application. The experimental process involved the reaction of 2-Aminomalononitrile 4-methylbenzenesulfonate(cas: 5098-14-6).Formula: C10H11N3O3S

The Article related to nitrile compound acetylcholinesterase monoamine oxidase alzheimer agent biol evaluation, ache inhibitors, alzheimer’s disease, aβ1-42 disaggregating agents, mao inhibitors, in silico study, nitrile-containing compounds and other aspects.Formula: C10H11N3O3S

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

On September 14, 2022, Mannarsamy, Maruthupandi; Nandeshwar, Muneshwar; Muduli, Gopendra; Prabusankar, Ganesan published an article.Application of 75629-62-8 The title of the article was Highly Active Cyclic Zinc(II) Thione Catalyst for C-C and C-N Bond Formation Reactions. And the article contained the following:

The first discrete seven-membered cyclic zinc(II) complex catalyzed room temperature Knoevenagel condensation reactions, and the synthesis of perimidine derivatives is reported under mild reaction conditions. The cyclic zinc(II) complex [(L)ZnBr2] (1) was isolated from the reaction between 1-(2-hydroxyethyl)-3-isopropyl-benzimidazol-2-thione (L, 2) and ZnBr2 (3). Complex 1 was characterized by different analytic techniques such as FTIR, CHNS, TGA, NMR, and SCXRD. The mononuclear zinc(II) complex 1 was used as a catalyst for Knoevenagel condensation reactions to isolate twenty different substituted methylene malononitriles with excellent yield. Besides, the zinc(II) thione complex 1 was used for the synthesis of 2,4-dihydroperimidine derivatives in a highly efficient manner. Catalyst 1 depicted wide substrate scopes. Overall, twenty different substituted methylene malononitriles and nine different perimidine derivatives were synthesized using catalyst 1 at room temperature The present study features a mild and fast synthetic approach along with excellent functional group tolerance. The experimental process involved the reaction of 2-((1H-Indol-3-yl)methylene)malononitrile(cas: 75629-62-8).Application of 75629-62-8

The Article related to preparation cyclic zinc hydroxyethylisopropylbenzimidazolthione coordination complex, crystal structure cyclic zinc hydroxyethylisopropylbenzimidazolthione coordination complex, thermal decomposition cyclic zinc hydroxyethylisopropylbenzimidazolthione coordination complex, knoevenagel condensation catalyst cyclic zinc hydroxyethylisopropylbenzimidazolthione coordination complex and other aspects.Application of 75629-62-8

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Bartlett, Robert T.; Cook, Alan F.; Holman, Michael J.; McComas, Warren W.; Nowoswait, Eugene F.; Poonian, Mohindar S.; Baird-Lambert, Judy A.; Baldo, Brian A.; Marwood, John F. published an article in 1981, the title of the article was Synthesis and pharmacological evaluation of a series of analogs of 1-methylisoguanosine.Product Details of 5098-14-6 And the article contains the following content:

Analogs of 1-methylisoguanosine (I, R = Me, R1 = H, R2 = OH) were evaluated as muscle relaxants, antiinflammatory agents, allergy inhibitors, and for cardiovascular activity. Cyclizing imidazole nucleoside II with RNCO (R = Et, Bu, octyl, Ph) and deprotecting gave I (R = Et, Bu, octyl, Ph; R1 = H, R2 = OH). Bromination of I (R = Me, R1 = H, R2 = OH) with Br2-H2O gave I (R = Me, R1 = Br, R2 = OH) which reacted with N2H4 to give I (R = Me, R1 = NHNH2, R2 = OH). This was cleaved with Raney Ni to give I (R = Me, R1 = NH2, R2 = OH). Deamination of 1-methylguanosine with NaNO2 in aqueous AcOH gave 1-methylxanthosine. Iodination of I (R = Me, R1 = H, R2 = OH) with Me(PhO)3P+I- gave I (R = Me, R1 = H, R2 = iodo) which was cyclized to III or deiodinated to I (R = Me, R1 = R2 = H). The phosphate ester I (R = Me, R1 = H, R2 = OPO32-) was prepared as well as cyclic phosphate IV. C-Nucleoside V was prepared from Me β-D-ribofuranosyl-1-carboximidate. Cyclizing the 9-(2-hydroxyethoxy)methyl analog of II with MeNCO gave acyclic analog VI. Similarly prepared was the β-D-arabinofuranosyl analog of I (R = Me, R1 = H, R2 = OH). The experimental process involved the reaction of 2-Aminomalononitrile 4-methylbenzenesulfonate(cas: 5098-14-6).Product Details of 5098-14-6

The Article related to isoguanosine analog pharmaceutical preparation, antiinflammatory isoguanosine analog preparation, heart rate isoguanosine analog preparation, allergy isoguanosine analog preparation, muscle relaxant isoguanosine analog preparation, antihypertensive isoguanosine analog preparation, hypothermia isoguanosine analog preparation, nucleoside pharmaceutical preparation and other aspects.Product Details of 5098-14-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

On October 1, 2010, Peng, Jing; Huang, Xin; Cui, Hai-Lei; Chen, Ying-Chun published an article.SDS of cas: 2510-01-2 The title of the article was Organocatalytic and Electrophilic Approach to Oxindoles with C3-Quaternary Stereocenters. And the article contained the following:

A Lewis base-catalyzed asym. allylic alkylation of Morita-Baylis-Hillman carbonates derived from isatins has been investigated, which provides an electrophilic pathway to access oxindoles, e.g. I, bearing C3-quaternary stereocenters. Excellent diastereoselectivity and high enantioselectivity have been obtained in the vinylogous functionalization of α,α-dicyanoolefin nucleophiles, giving multifunctional products with vicinal quaternary and tertiary chiral carbon centers. The experimental process involved the reaction of 2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile(cas: 2510-01-2).SDS of cas: 2510-01-2

The Article related to organocatalytic electrophilic oxindole preparation enantioselective diastereoselective allylic alkylation, spirocyclic oxindole preparation diastereoselective enantioselective intramol michael addition cyclization, lewis base catalyst allylic alkylation dicyanoolefin oxindole carbonate reactant, quaternary oxindole preparation stereoselective allylic alkylation and other aspects.SDS of cas: 2510-01-2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

On May 22, 2008, Ohlmeyer, Michael J.; Bohnstedt, Adolph; Kingsbury, Celia; Ho, Koc-Kan; Quintero, Jorge published a patent.Synthetic Route of 138801-92-0 The title of the patent was Preparation of 7-substituted purine derivatives as inhibitors of tyrosine kinase Jak3 for immunosuppression. And the patent contained the following:

The present invention provides novel purinone and related derivatives [I; Q1, Q2 = independently CX1, CX2, or N wherein Q1 and Q2 are not both N; Q3 = N or CH; X1, X2 = independently H, C1-6 alkyl, cyano, halo, halo-C1-6 alkyl, HO, C1-6 alkoxy, halo-C1-6 alkoxy, or NO2; R1 = H, C1-6 alkyl; y = 0 or an integer of 1-3 ; R2 and R3 are selected independently for each occurrence of (CR2R3) from H and C1-6 alkyl; R4 = each (un)substituted alkyl, heterocyclyl, aryl, or heteroaryl; R5 = alkyl, (un)substituted heterocyclyl, or C1-C6 alkyl wherein (a) one or two CH2 is replaced by a group chosen from NH and N(alkyl); (b) one or two CH2 is replaced by O; (c) one or two CH2 is replaced by (C:O); (d) two CH2 are replaced by CH:CH or CC; or (e) any chem. stable combination of (a), (b) (c) and (d); and wherein from zero to three hydrogens is replaced by a substituent chosen from: (a) halogen, hydroxy, cyano, lower alkylsulfonyl, lower alkylsulfonyloxy, amino, lower alkylamino, di(lower alkyl)amino, alkoxyamino, sulfonylamino, acylamino, arylamino, lower alkoxy; (b) (un)substituted heterocyclyl; (c) (un)substituted Ph; and (d) (un)substituted heteroaryl]. These compounds are inhibitors of Jak3 kinase and useful for the prevention and treatment of autoimmune diseases, inflammatory disease, mast cell mediated disease, hematol. malignancy, and transplant rejection. Thus, a solution of 20 mg 3-[9-((R)-6,8-difluorochroman-4-yl)-8-oxo-8,9-dihydro-7H-purin-2-yl]-3H-benzo[d]imidazole-5-carbonitrile in 2 mL MeCN was treated with 90 mg Me bromoacetate and 100 mg 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine on polystyrene (2.2 mmol base/g) and the mixture was stirred at room temperature 48 h, and then filtered to give, after concentration of the filtrate in vacuo, Me 2-[2-(6-cyano-1H-benzo[d]imidazol-1-yl)-9-((R)-6,8-difluorochroman-4-yl)-8-oxo-8,9-dihydropurin-7-yl]acetate (II). The compounds I including II showed IC50 of 101 nM-1 μM against tyrosine kinase Jak3. The experimental process involved the reaction of 4-Oxochroman-6-carbonitrile(cas: 138801-92-0).Synthetic Route of 138801-92-0

The Article related to purine derivative preparation immunosuppressant, autoimmune disease inflammatory disease prevention treatment purine derivative preparation, mast cell mediated disease prevention treatment purine derivative preparation, hematol malignancy transplant rejection prevention treatment purine derivative preparation, tyrosine kinase jak3 inhibitor purine derivative and other aspects.Synthetic Route of 138801-92-0

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts