Tag: M.W=250-300

Bartlett, Robert T. published the artcileSynthesis and pharmacological evaluation of a series of analogs of 1-methylisoguanosine, Recommanded Product: 2-Aminomalononitrile 4-methylbenzenesulfonate, the publication is Journal of Medicinal Chemistry (1981), 24(8), 947-54, database is CAplus and MEDLINE.

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 = OPO₃^2-) 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).

Journal of Medicinal Chemistry published new progress about 5098-14-6. 5098-14-6 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Salt,Sulfonic acid,Amine,Benzene, name is 2-Aminomalononitrile 4-methylbenzenesulfonate, and the molecular formula is C10H11N3O3S, Recommanded Product: 2-Aminomalononitrile 4-methylbenzenesulfonate.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Rosowsky, Andre published the artcileMethotrexate analogs. 4. 7-Methyl derivatives of methotrexate and dichloromethotrexate. New synthesis and some biological studies, HPLC of Formula: 5098-14-6, the publication is Journal of Medicinal Chemistry (1974), 17(12), 1308-11, database is CAplus and MEDLINE.

Conversion of methotrexate (I) [59-05-2] and 3′,5′-dichloromethotrexate (II) [528-74-5] to their 7-methyl analogs III [35190-25-1] and IV [53729-18-3], resp., to prevent metabolism in vivo to the inactive 7-hydroxy derivatives resulted in marked loss of antileukemic activity in mice and in vitro and loss of inhibitory potency against purified dihydrofolate reductase [9002-03-3] from Lactobacillus casei and L1210-FR8 tumor. The lack of antitumor activity presumably resulted from impaired enzyme binding. III was prepared from 2-amino-5-chloromethyl-3-cyano-6-methylpyrazine 1-oxide [53661-20-4] and diethyl N-(p-N-methylaminobenzoyl)glutamate [2378-95-2] by the method of E. C. Taylor, et al. (1973).

Journal of Medicinal Chemistry published new progress about 5098-14-6. 5098-14-6 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Salt,Sulfonic acid,Amine,Benzene, name is 2-Aminomalononitrile 4-methylbenzenesulfonate, and the molecular formula is C10H11N3O3S, HPLC of Formula: 5098-14-6.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Jeong, Susan published the artcileMacrocyclic Triarylethylenes via Heck Endocyclization: A System Relevant to Diazonamide Synthesis, COA of Formula: C10H11N3O3S, the publication is Journal of Organic Chemistry (1998), 63(24), 8640-8641, database is CAplus.

The author’s approach the preparation of diazonamide A (I) synthesis is described. Initial results show that Heck endocyclization can form highly functionalized lactam rings containing an imbedded 1,2-diaryl-1-(5-oxazolyl)ethylene. Thus, cross-coupling of vinylstannane II (PMB = p-methoxybenzyl) with functionalized oxazole III (prepared in 2 steps from Boc-Val-OH and aminomalononitrile tosylate) gave phenol IV in 89% yield after deprotection. Peptide coupling of IV with a protected O-benzyl-3-iodotyrosine derivative, followed by Pd-catalyzed macrocyclization gave macrocycle V, which contains the diazonamide AEF ring system.

Journal of Organic Chemistry published new progress about 5098-14-6. 5098-14-6 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Salt,Sulfonic acid,Amine,Benzene, name is 2-Aminomalononitrile 4-methylbenzenesulfonate, and the molecular formula is C10H11N3O3S, COA of Formula: C10H11N3O3S.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Shey, Chun Feng published the artcileSynthesis of 2,4-diamino-6-substituted pteridine, Product Details of C10H11N3O3S, the publication is Shida Xuebao (Taipei) (1984), 631-43, database is CAplus.

Title compounds I (R = Cl, OH), intermediates for methotrexate, were prepared Thus, cyclocondensation of 2,4,5,6-tetraaminopyrimidine with CO(CH₂OH)₂ gave I (R = OH) whereas cyclocondensation of 2-amino-3-cyano-5-chloromethylpyrazine with guanidine gave I (R = Cl).

Shida Xuebao (Taipei) published new progress about 5098-14-6. 5098-14-6 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Salt,Sulfonic acid,Amine,Benzene, name is 2-Aminomalononitrile 4-methylbenzenesulfonate, and the molecular formula is C25H47NO8, Product Details of C10H11N3O3S.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Tuo, Wei published the artcileDevelopment of novel oxazolo[5,4-d]pyrimidines as competitive CB₂ neutral antagonists based on scaffold hopping, Application In Synthesis of 5098-14-6, the publication is European Journal of Medicinal Chemistry (2018), 68-78, database is CAplus and MEDLINE.

A series of novel oxazolo[5,4-d]pyrimidines I [R¹ = H, Cl, F, CF₃; R² = H, Me; R³ = n-Bu, cyclohexylmethyl, 1-methylpiperazinyl, etc.] was designed via a scaffold hopping strategy and synthesized through a newly developed approach. All these compounds I were evaluated for their biol. activity toward CB₁/CB₂ cannabinoid receptors, their metabolic stability in mice liver microsomes and their cytotoxicity against several cell lines. Eight compounds I [R¹ = Cl, CF₃; R² = H, Me; R³ = 1-methylpiperazinyl, 1-ethylpiperazinyl, 1-acetylpiperazinyl] were identified as CB₂ ligands with K_i values less than 1 ΜM. It was noteworthy that compounds I [R¹ = Cl; R² = Me; R³ = 1-methylpiperazinyl, 1-ethylpiperazinyl] showed CB₂ binding affinity in the nanomolar range and significant selectivity over CB₁ receptors. Interestingly, functionality studies imply that they behaved as competitive neutral antagonists. Moreover, all tested compounds I were devoid of cytotoxicity toward several cell lines, including Chinese hamster ovary cells (CHO) and human colorectal adenocarcinoma cells HT29.

European Journal of Medicinal Chemistry published new progress about 5098-14-6. 5098-14-6 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Salt,Sulfonic acid,Amine,Benzene, name is 2-Aminomalononitrile 4-methylbenzenesulfonate, and the molecular formula is C12H16O3, Application In Synthesis of 5098-14-6.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Morwick, Tina published the artcileEvolution of the Thienopyridine Class of Inhibitors of IκB Kinase-β: Part I: Hit-to-Lead Strategies, Application of 2-Aminomalononitrile 4-methylbenzenesulfonate, the publication is Journal of Medicinal Chemistry (2006), 49(10), 2898-2908, database is CAplus and MEDLINE.

High-throughput screening is routinely employed as a method for the identification of novel hit structures. Large numbers of active compounds are typically procured in this way and must undergo a rigorous validation process. This process is described in detail for a collection of screening hits identified as inhibitors of IκB kinase-β (IKKβ), a key regulatory enzyme in the nuclear factor-κB (NF-κB) pathway. From these studies, a promising hit series was selected. Subsequent lead generation activities included the development of a pharmacophore hypothesis and structure-activity relationship (SAR) for the hit series. This led to the exploration of related scaffolds offering addnl. opportunities, and the various structural classes were comparatively evaluated for enzyme inhibition, selectivity, and drug-like properties. A novel lead series of thienopyridines was thereby established, and this series advanced into lead optimization for further development.

Journal of Medicinal Chemistry published new progress about 5098-14-6. 5098-14-6 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Salt,Sulfonic acid,Amine,Benzene, name is 2-Aminomalononitrile 4-methylbenzenesulfonate, and the molecular formula is C10H11N3O3S, Application of 2-Aminomalononitrile 4-methylbenzenesulfonate.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Taylor, Edward C. published the artcilePteridines. Part XLII. Synthesis of some benzo[g]pteridines. A novel aromatization reaction, Application of 2-Aminomalononitrile 4-methylbenzenesulfonate, the publication is Heterocycles (1977), 6(4), 449-57, database is CAplus.

The benzopteridine I (R = NH2, R1 = R2 = H) was prepared by condensing 6-chloro-2-oximinocyclohexanone-HCl with H2NCH(CN)2.4-MeC6H4SO3H, aromatizing the quinoxaline oxide II by heating with HOAc, and condensing 2-amino-3-cyanoquinoxaline (III) with guanidine-HCl. Condensation of III with HC(OEt)3 gave I (R-R2 = H). I (R = NH2, R1 = R2 = H) was treated with HCl to give benzo[g]pterin. I [R = NH2, R1R2 = (CH)4] was obtained from 2-oximino-1-tetralone.

Heterocycles published new progress about 5098-14-6. 5098-14-6 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Salt,Sulfonic acid,Amine,Benzene, name is 2-Aminomalononitrile 4-methylbenzenesulfonate, and the molecular formula is C5H6N2O2, Application of 2-Aminomalononitrile 4-methylbenzenesulfonate.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Taylor, Edward C. published the artcilePteridines. 41. Synthesis and dihydrofolate reductase inhibitory activity of some cycloalka[g]pteridines, Computed Properties of 5098-14-6, the publication is Journal of Medicinal Chemistry (1977), 20(9), 1215-18, database is CAplus and MEDLINE.

Eleven homologous 2,4-diaminocycloalka[g]pteridines and derivatives with cycloalkane ring size varying from 5 to 15 were prepared by cyclic condensation of aminomalonitrile tosylate [5098-14-6] with α-oximinocycloalkanones to give aminocyanocycloalka[b]pyrazine oxides followed by deoxygenation and guanidine cyclization, or guanidine cyclization of the pyrazine oxides followed by deoxygenation, or by condensation of 2,4,5,6-tetraaminopyrimidine-HCl [39944-62-2] with a cycloalka-1,2-dione. Inhibition of dihydrofolate reductase [9002-03-3] from Lactobacillus casei, rat liver, L1210, and Trypanosoma cruzi depended on cycloalkane ring size, with 2,4-diaminocyclododeca[g]pteridine (I) [53274-34-3] being most active.

Journal of Medicinal Chemistry published new progress about 5098-14-6. 5098-14-6 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Salt,Sulfonic acid,Amine,Benzene, name is 2-Aminomalononitrile 4-methylbenzenesulfonate, and the molecular formula is C10H16O2, Computed Properties of 5098-14-6.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Haight, Anthony R. published the artcileA Scaleable Synthesis of Fiduxosin, Name: 2-Aminomalononitrile 4-methylbenzenesulfonate, the publication is Organic Process Research & Development (2004), 8(6), 897-902, database is CAplus.

Fiduxosin (I) is under development for the treatment of benign prostatic hyperplasia. A convergent strategy required methodologies for preparation of an enantiomerically pure 3,4-cis-disubstituted pyrrolidine and a 2,3,5-trisubstituted thienopyrazine in a regiospecific manner. A [3+2] cycloaddition of an enantiopure azomethine ylide followed by a diastereoselective crystallization was employed to prepare the benzopyranopyrrolidine in high diastereomeric and enantiomeric purity. Conditions for reduction of an O-aryl lactone susceptible to epimerization were developed, and cyclization of the alc./phenol to the ether was accomplished in high yield. The thienopyrazine was prepared by condensation of Me thioglycolate and a regiospecifically prepared 2-bromo-3-cyano-5-phenylpyrazine. Conditions for effective halogen substitutive deamination to prepare regiospecific trisubstituted pyrazines is described.

Organic Process Research & Development published new progress about 5098-14-6. 5098-14-6 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Salt,Sulfonic acid,Amine,Benzene, name is 2-Aminomalononitrile 4-methylbenzenesulfonate, and the molecular formula is C10H11N3O3S, Name: 2-Aminomalononitrile 4-methylbenzenesulfonate.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Cheng, Qiuli published the artcileAntifouling and Antibacterial Polymer-Coated Surfaces Based on the Combined Effect of Zwitterions and the Natural Borneol, Recommanded Product: 2-Aminomalononitrile 4-methylbenzenesulfonate, the publication is ACS Applied Materials & Interfaces (2021), 13(7), 9006-9014, database is CAplus and MEDLINE.

The development and application of natural antibacterial materials have always been the focus of biomedical research. Borneol as a natural antibacterial compound has received extensive attention. However, the hydrophobicity caused by its unique structure limits its application range to a certain extent. In this study, we combine zwitterionic 2-methacryloyloxyethyl phosphorylcholine (MPC) with a complex bicyclic monoterpene structure borneol compound and prepare an excellent antifouling and antibacterial surface via the Schiff-base bond. The prepared coating has excellent hydrophilicity verified by the contact angle (CA), and its polymer layer is confirmed by XPS. The zwitterion MPC and borneol moieties in the copolymer play a coordinating role, relying on super hydration and the special stereochem. structure to prevent protein adsorption and inhibit bacterial adhesion, resp., which are demonstrated by bovine serum albumin (BSA) adsorption and antibacterial activity test. Moreover, the water-soluble borneol derivative as the antibacterial surfaces we designed here was biocompatible toward MRC-5 (lung fibroblasts), as showed by in vitro cytotoxicity assays. Such results indicate the potential application of the as-prepared hydrophilic surfaces in the biomedical materials.

ACS Applied Materials & Interfaces published new progress about 5098-14-6. 5098-14-6 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Salt,Sulfonic acid,Amine,Benzene, name is 2-Aminomalononitrile 4-methylbenzenesulfonate, and the molecular formula is C10H11N3O3S, Recommanded Product: 2-Aminomalononitrile 4-methylbenzenesulfonate.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts