Tag: M.W=100-150

Shaik, Jeelan Basha published the artcileSynthesis, Biological Evaluation, and Molecular Docking of 8-imino-2-oxo-2H,8H-pyrano[2,3-f]chromene Analogs: New Dual AChE Inhibitors as Potential Drugs for the Treatment of Alzheimer’s Disease, Name: 2-Cyano-N-ethylacetamide, the publication is Chemical Biology & Drug Design (2016), 88(1), 43-53, database is CAplus and MEDLINE.

Alzheimer’s disease onset and progression are associated with the dysregulation of multiple and complex physiol. processes, and a successful therapeutic approach should therefore address more than one target. In line with this modern paradigm, a series of 8-imino-2-oxo-2H,8H-pyrano[2,3-f]chromene analogs (4a-q) were synthesized and evaluated for their multitarget-directed activity on acetylcholinesterase, butyrylcholinesterase (BuChE), 2,2′-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS) radical, and amyloid-β peptide (Aβ) specific targets for Alzheimer’s disease therapy. Most of the synthesized compounds showed remarkable acetylcholinesterase inhibitory activities in low nM concentrations and good ABTS radical scavenging activity, however, no evidence of BuChE inhibitory activity. Among them, 3-bromobenzylamide derivative N-(3-bromobenzyl)-8-imino-2-oxo-2H,8H-pyrano [2,3-f]chromene-9-carboxamide (4m) exhibited the best acetylcholinesterase inhibitory activity with IC₅₀ value of 13±1.4 nM which is 51-fold superior to galantamine, a reference drug. Kinetic and mol. docking studies indicated (4m) as mixed-type inhibitor, binding simultaneously to catalytic active and peripheral anionic sites of acetylcholinesterase. Five compounds N-cyclohexyl-8-imino-2-oxo-2H,8H-pyrano[2,3-f] chromene-9-carboxamide (4e), 8-imino-9-(morpholine-4-carbonyl)-2H,8H-pyrano [2,3-f]chromen-2-one (4f), N-benzyl-8-imino-2-oxo-2H,8H-pyrano[2,3-f] chromene-9-carboxamide (4g), 8-imino-N-(1-(4-methoxyphenyl)ethyl)-2-oxo-2H,8H- pyrano[2,3-f]chromene-9-carboxamide (4j), and N-(2,4-dimethoxybenzyl)-8-imino-2-oxo-2H,8H- pyrano[2,3-f]chromene-9-carboxamide (4k) have shown 1.4- to 2.5-fold of higher antioxidant activities than trolox. Interestingly, the most active compound (4m) demonstrated dosage-dependent acceleration of Aβ_1-42 aggregation, which may reduce toxicity of oligomers. Overall, these results lead to discovery of fused tricyclic coumarins as promising dual binding site inhibitors of acetylcholinesterase and afford multifunctional compounds with potential impact for further pharmacol. development in Alzheimer’s therapy.

Chemical Biology & Drug Design published new progress about 15029-36-4. 15029-36-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Aliphatic hydrocarbon chain,Amide, name is 2-Cyano-N-ethylacetamide, and the molecular formula is C12H10O4S, Name: 2-Cyano-N-ethylacetamide.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Delledonne, Andrea published the artcileBis-isonicotinoyl linkers containing polyaromatic scaffolds: synthesis, structure and spectroscopic properties, Safety of Isonicotinamide, the publication is Physical Chemistry Chemical Physics (2022), 24(2), 1191-1201, database is CAplus and MEDLINE.

New synthesis of extended linkers containing different polyaromatic chromophores functionalized with isonicotinoyl moieties I (R = 3,7-naphthalene-diyl, biphenyl-4,4′-diyl, fluorene-2,7-diyl, etc.) have been synthesized by Pd-catalyzed cross-coupling reactions involving isonicotinamide and the appropriate aromatic dibromides such as 2,6-dibromonaphthalene, 2,7-dibromofluorene, 9,10-dibromoanthracene, etc. The optimized protocol led to the isolation of the target mols. in good yield and with high purity. Electronic absorption and emission spectra were collected both in solution (DMF) and in the solid state. TDDFT calculations were carried out to investigate the effect of the isonicotinoyl moieties on the spectral features of the central chromophores.

Physical Chemistry Chemical Physics published new progress about 1453-82-3. 1453-82-3 belongs to amides-buliding-blocks, auxiliary class Pyridine,Amine,Amide, name is Isonicotinamide, and the molecular formula is C6H6N2O, Safety of Isonicotinamide.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Matulenko, Mark A. published the artcile5-(3-Bromophenyl)-7-(6-morpholin-4-ylpyridin-3-yl)pyrido[2,3-d]pyrimidin-4-ylamine: structure-activity relationships of 7-substituted heteroaryl analogs as non-nucleoside adenosine kinase inhibitors, HPLC of Formula: 14294-10-1, the publication is Bioorganic & Medicinal Chemistry (2005), 13(11), 3705-3720, database is CAplus and MEDLINE.

4-Amino-5,7-disubstituted pyridopyrimidines are potent, non-nucleoside inhibitors of adenosine kinase (AK). The authors recently identified a potent, orally efficacious analog I containing a 7-pyridylmorpholine substituted ring system as the key structural element of this template. The pharmacol. effects of five- and six-membered heterocyclic ring replacements for the pyridine ring in I are reported. These replacements were found to have interesting effects on in vivo efficacy and genotoxicity as well as in vitro potency. The authors discovered that the nitrogen in the heterocyclic ring at C(7) is important for the modulation of mutagenic side effects (Ames assay).

Bioorganic & Medicinal Chemistry published new progress about 14294-10-1. 14294-10-1 belongs to amides-buliding-blocks, auxiliary class Morpholine,Thiourea,Amine,Amide, name is Morpholine-4-carbothioamide, and the molecular formula is C5H10N2OS, HPLC of Formula: 14294-10-1.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Kim, Paul published the artcileA study to discover novel pharmaceutical cocrystals of pelubiprofen with a machine learning approach compared, Name: Isonicotinamide, the publication is CrystEngComm (2022), 24(21), 3938-3952, database is CAplus.

Pelubiprofen (PF), a biopharmaceutical classification system (BCS) class II non-steroidal anti-inflammatory drug, has been on the market only in its crystalline form. To discover the first cocrystal form(s) of the drug, artificial neural network (ANN) modeling and the pKa rule were adopted to predict the most probable coformers that could form cocrystals with PF. Among candidate mols. examined theor. and exptl., isonicotinamide (INA) and nicotinamide (NCA) formed PF-based cocrystals through evaporative crystallization The structures of the PF-INA and PF-NCA cocrystals were verified through multiple characterization techniques, including single-crystal X-ray diffraction. These two cocrystals demonstrated remarkably better water solubility and dissolution behaviors than did pure PF in both acidic and neutral solutions Even with deficiency in the prediction capability, the combination of machine learning-based and knowledge-based coformer screening and the subsequent synthetic experiments would be a potential approach for discovering novel pharmaceutical cocrystals in the future.

CrystEngComm published new progress about 1453-82-3. 1453-82-3 belongs to amides-buliding-blocks, auxiliary class Pyridine,Amine,Amide, name is Isonicotinamide, and the molecular formula is C6H6N2O, Name: Isonicotinamide.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Griffiths, John published the artcileSynthesis, light absorption and fluorescence properties of new thiazole analogues of the xanthene dyes, Recommanded Product: Morpholine-4-carbothioamide, the publication is Dyes and Pigments (2003), 57(2), 107-114, database is CAplus.

The synthesis of a new class of cationic dye is described, whose chromophoric system is formally related to that of the cationic xanthene dyes in which one of the aminophenyl rings is replaced by a 2-aminothiazole ring. The light absorption and fluorescence properties of a range of representative dyes of this type have been investigated. The dyes were found to absorb at shorter wavelengths than their xanthene analogs (λ_max 490-506 nm in methanol), in agreement with theor. predictions, and they also showed moderate to intense fluorescence in dichloromethane solution, with Stokes shifts ranging from 33 to 50 nm.

Dyes and Pigments published new progress about 14294-10-1. 14294-10-1 belongs to amides-buliding-blocks, auxiliary class Morpholine,Thiourea,Amine,Amide, name is Morpholine-4-carbothioamide, and the molecular formula is C5H10N2OS, Recommanded Product: Morpholine-4-carbothioamide.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Fefelova, S. R. published the artcileRegioselective Synthesis of Pyridin-2-One Derivatives Based on Ethyl(1-Phenylethylidene)Cyanoacetate and Cyanoacetamides, HPLC of Formula: 15029-36-4, the publication is Chemistry of Heterocyclic Compounds (New York, NY, United States) (2014), 50(8), 1133-1136, database is CAplus.

Et (1-phenylethylidene)cyanoacetate reacted with cyanoacetamides in an alc. solution of sodium ethoxide, forming various pyridin-2-ones. The cyclization direction of the Michael adducts was affected by the nucleophilicity of the cyanoacetamide used as a CH acid.

Chemistry of Heterocyclic Compounds (New York, NY, United States) published new progress about 15029-36-4. 15029-36-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Aliphatic hydrocarbon chain,Amide, name is 2-Cyano-N-ethylacetamide, and the molecular formula is C5H8N2O, HPLC of Formula: 15029-36-4.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Kutschy, P. published the artcileReactivity of N’-substituted N-(4-pentynoyl)- and N-[2-(2-propynyl)-4-pentynoyl]thioureas, Category: amides-buliding-blocks, the publication is Chemical Papers (1987), 41(4), 519-26, database is CAplus.

Treatment of HCCCH₂CHRCONHCSNR¹R² (I; R = H, HCCCH₂; R¹, R² = H, Ph; R¹R²N = morpholino) with EtONa and HgCl₂ or Hg(OAc)₂ resp., results in splitting-off the acyl residue and formation of H₂NCSNR¹R². Heating I (R = HCCCH₂, R¹R²N = morpholino) EtOH with a catalytic amount of TiCl₃ gave 58% (HCCCH₂)₂CHCONHCSOEt. Treating I (R = H, HCCCH₂; R¹ = R² = Ph) with Br₂ in CHCl₃ gave 80-87% the benzothiazoline derivatives II (R = H, HCCCH₂).

Chemical Papers published new progress about 14294-10-1. 14294-10-1 belongs to amides-buliding-blocks, auxiliary class Morpholine,Thiourea,Amine,Amide, name is Morpholine-4-carbothioamide, and the molecular formula is C5H10N2OS, Category: amides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Rastogi, R. R. published the artcileKetene SS-acetals. Part 10. Reaction of α-oxoketene SS-acetals with N-alkylcyanoacetamides: a new general method for substituted and fused 2,7-dialkyl-8-amino-5-cyano-2,7-naphthyridine-1,6(2H,7H)-diones, Formula: C5H8N2O, the publication is Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) (1978), 554-8, database is CAplus.

The reaction of α-oxoketene dithioacetals with NCCH₂CONHR (I; R = Me, Et) in the presence of NaOCHMe₂ gave 25-93% 2,7-naphthyridine derivatives via N-alkylpyridone intermediates. E.g., naphthyridine II was obtained (38%) by reaction of (MeS)₂C:CHCOPh with I (R = Me). (MeS)₂C:CRCN (III; R = Ph, p-ClC₆H₄, CN) gave 46-68% pyridones IV (R = Me, Et, R¹ = Ph, p-ClC₆H₄, CN) under similar conditions, whereas cyclic ketene dithioacetals V (n = 1,2) gave 71-80% fused naphthyridines VI (n = 1, 2, R = Me, Et). Naphthonaphthyridones VII (R = Me, Et; n = 1, R¹ = H, OMe; n = 2, R¹ = H) were obtained in high yield from the reaction of ketene dithioacetals VIII (n = 1, R¹ = H, OMe; n = 2, R = H) with I (R = Me, Et).

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) published new progress about 15029-36-4. 15029-36-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Aliphatic hydrocarbon chain,Amide, name is 2-Cyano-N-ethylacetamide, and the molecular formula is C5H8N2O, Formula: C5H8N2O.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Yokoyama, Masataka published the artcileS,N double rearrangement. 3. Reaction mechanism, Product Details of C5H8N2O, the publication is Journal of Organic Chemistry (1984), 49(1), 74-8, database is CAplus.

¹³C-labeling and crossover experiments indicated that cyclizations such as that of I with BzOH to give II proceed via a thiaallylic rearrangement of the initial ring-closure product formed from the CN and SH groups and BzOH.

Journal of Organic Chemistry published new progress about 15029-36-4. 15029-36-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Aliphatic hydrocarbon chain,Amide, name is 2-Cyano-N-ethylacetamide, and the molecular formula is C7H7ClN2, Product Details of C5H8N2O.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Kuhnert, Maren published the artcileTracing Binding Modes in Hit-to-Lead Optimization: Chameleon-Like Poses of Aspartic Protease Inhibitors, Formula: C5H8N2O, the publication is Angewandte Chemie, International Edition (2015), 54(9), 2849-2853, database is CAplus and MEDLINE.

Successful lead optimization in structure-based drug discovery depends on the correct deduction and interpretation of the underlying structure-activity relationships (SAR) to facilitate efficient decision-making on the next candidates to be synthesized. Consequently, the question arises, how frequently a binding mode (re)-validation is required, to ensure not to be misled by invalid assumptions on the binding geometry. We present an example in which minor chem. modifications within one inhibitor series lead to surprisingly different binding modes. X-ray structure determination of eight inhibitors derived from one core scaffold resulted in four different binding modes in the aspartic protease endothiapepsin, a well-established surrogate for e.g. renin and β-secretase. In addition, we suggest an empirical metrics that might serve as an indicator during lead optimization to qualify compounds as candidates for structural revalidation.

Angewandte Chemie, International Edition published new progress about 15029-36-4. 15029-36-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Aliphatic hydrocarbon chain,Amide, name is 2-Cyano-N-ethylacetamide, and the molecular formula is C5H8N2O, Formula: C5H8N2O.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics