Category: amides-buliding-blocks

Rydfjord, Jonas published the artcileRoute to 3-Amidino Indoles via Pd(II)-Catalyzed C-H Bond Activation, Quality Control of 2451-91-4, the publication is Organic Letters (2017), 19(15), 4066-4069, database is CAplus and MEDLINE.

We report a facile synthesis of 3-amidino indoles from indoles and cyanamides. The reaction is Pd(II)-catalyzed and proceeds via C-H bond activation of the indole in its 3-position followed by a 1,2-addition of the resulting indole-palladium σ-complex to a cyanamide, which provides the corresponding amidine. The preference for 4,5-diazafluoren-9-one (DAF) as the ligand is investigated using DFT calculations, and a plausible reaction pathway is presented.

Organic Letters published new progress about 2451-91-4. 2451-91-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Benzene, name is N,N-Dibenzylcyanamide, and the molecular formula is C15H14N2, Quality Control of 2451-91-4.

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

Getlik, Matthaus published the artcileStructure-Based Optimization of a Small Molecule Antagonist of the Interaction Between WD Repeat-Containing Protein 5 (WDR5) and Mixed-Lineage Leukemia 1 (MLL1), SDS of cas: 947533-21-3, the publication is Journal of Medicinal Chemistry (2016), 59(6), 2478-2496, database is CAplus and MEDLINE.

WD repeat-containing protein 5 (WDR5) is an important component of the multiprotein complex essential for activating mixed-lineage leukemia 1 (MLL1). Rearrangement of the MLL1 gene is associated with onset and progression of acute myeloid and lymphoblastic leukemias, and targeting the WDR5-MLL1 interaction may result in new cancer therapeutics. Our previous work showed that binding of small mol. ligands to WDR5 can modulate its interaction with MLL1, suppressing MLL1 methyltransferase activity. Initial structure-activity relationship studies identified N-(2-(4-methylpiperazin-1-yl)-5-substituted-phenyl) benzamides as potent and selective antagonists of this protein-protein interaction. Guided by crystal structure data and supported by in silico library design, we optimized the scaffold by varying the C-1 benzamide and C-5 substituents. This allowed us to develop the first highly potent (K_disp < 100 nM) small mol. antagonists of the WDR5-MLL1 interaction and demonstrate that N-(4-(4-methylpiperazin-1-yl)-3′-(morpholinomethyl)-[1,1′-biphenyl]-3-yl)-6-oxo-4-(trifluoromethyl)-1,6-dihydropyridine-3-carboxamide 16d (OICR-9429) is a potent and selective chem. probe suitable to help dissect the biol. role of WDR5.

Journal of Medicinal Chemistry published new progress about 947533-21-3. 947533-21-3 belongs to amides-buliding-blocks, auxiliary class Pyridine,Boronic acid and ester,Amine,Amide,Boronic Acids,Boronic Acids,Boronic acid and ester,, name is (6-Acetamidopyridin-3-yl)boronic acid, and the molecular formula is C7H9BN2O3, SDS of cas: 947533-21-3.

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

Melekhova, Anna A. published the artcileCopper(I)-Catalyzed 1,3-Dipolar Cycloaddition of Ketonitrones to Dialkylcyanamides: A Step toward Sustainable Generation of 2,3-Dihydro-1,2,4-oxadiazoles, HPLC of Formula: 2451-91-4, the publication is ACS Omega (2017), 2(4), 1380-1391, database is CAplus and MEDLINE.

Cu^I -catalyzed cycloaddition of the ketonitrones Ph₂C=N⁺ (R’)O^– (R’ = Me, CH₂Ph) to the disubstituted cyanamides NCNR₂ (R = Me₂ , Et₂ , (CH₂)₄ , (CH₂)₅ , (CH₂)₄O, C₉H₁₀, (CH₂Ph)₂ , Ph(Me)) gives corresponding 5-aminosubstituted 2,3-dihydro- 1,2,4-oxadiazoles (16 examples) in good to moderate yields. The reaction proceeds under mild conditions (CH₂Cl₂ , RT or 45 °C) and requires 10 mol% of [Cu(NCMe)₄](BF₄) as the catalyst. Somehow reduced yields are due to the individual properties of 2,3- dihydro-1,2,4-oxadiazoles, which easily undergo ring-opening via the N-O bond splitting. Results of the DFT calculations reveal that the cycloaddition of ketonitrones to Cu^I -bound cyanamides is a concerted process and the copper-catalyzed reaction is controlled by the predominant contribution of HOMO_dipole-LUMO_{dipolarophile} interaction (group I by the Sustmann’s classification). Metal-involving process is much more asynchronous and profitable from both kinetic and thermodn. viewpoints than the hypothetical metal-free reaction.

ACS Omega published new progress about 2451-91-4. 2451-91-4 belongs to amides-buliding-blocks, auxiliary class Nitrile,Amine,Benzene, name is N,N-Dibenzylcyanamide, and the molecular formula is C15H14N2, HPLC of Formula: 2451-91-4.

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

Nasibullin, Igor published the artcileSynthetic prodrug design enables biocatalytic activation in mice to elicit tumor growth suppression, Recommanded Product: (S)-2-(N-((2′-(1H-Tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)pentanamido)-3-methylbutanoic acid, the publication is Nature Communications (2022), 13(1), 39, database is CAplus and MEDLINE.

Considering the intrinsic toxicities of transition metals, their incorporation into drug therapies must operate at minimal amounts while ensuring adequate catalytic activity within complex biol. systems. As a way to address this issue, this study investigates the design of synthetic prodrugs that are not only tuned to be harmless, but can be robustly transformed in vivo to reach therapeutically relevant levels. To accomplish this, retrosynthetic prodrug design highlights the potential of naphthylcombretastatin-based prodrugs, which form highly active cytostatic agents via sequential ring-closing metathesis and aromatization. Structural adjustments will also be done to improve aspects related to catalytic reactivity, intrinsic bioactivity, and hydrolytic stability. The developed prodrug therapy is found to possess excellent anticancer activities in cell-based assays. Furthermore, in vivo activation by i.v. administered glycosylated artificial metalloenzymes can also induce significant reduction of implanted tumor growth in mice.

Nature Communications published new progress about 137862-53-4. 137862-53-4 belongs to amides-buliding-blocks, auxiliary class GPCR/G Protein,Angiotensin Receptor, name is (S)-2-(N-((2′-(1H-Tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)pentanamido)-3-methylbutanoic acid, and the molecular formula is C24H29N5O3, Recommanded Product: (S)-2-(N-((2′-(1H-Tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)pentanamido)-3-methylbutanoic acid.

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

Watanabe, M. published the artcileTandem directed metalation reactions. Short syntheses of polycyclic aromatic hydrocarbons and ellipticine alkaloids, COA of Formula: C10H14N2O, the publication is Journal of the American Chemical Society (1980), 102(4), 1457-60, database is CAplus.

Starting with N,N-diethylbenzamides and aromatic aldehydes and proceeding via ortho lithiated intermediates, a one-pot synthesis of anthraquinones, e.g. I and II, was achieved. The scope and limitations of this tandem metalation sequence was explored for a variety of aromatic and heteroaromatic amides and aldehydes. The use of this reaction for the short syntheses of carcinogenic polycyclic aromatic hydrocarbons and antitumor ellipticine alkaloids, e.g. III was demonstrated.

Journal of the American Chemical Society published new progress about 530-40-5. 530-40-5 belongs to amides-buliding-blocks, auxiliary class Pyridine,Amine,Amide, name is N,N-Diethylisonicotinamide, and the molecular formula is C12H25Br, COA of Formula: C10H14N2O.

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

Zhao, Yigang published the artcileC-H Activation by Amide Chelation Control: Ruthenium-Catalyzed Direct Synthesis of 2-Aryl-3-furanamides, Formula: C10H14N2O, the publication is Advanced Synthesis & Catalysis (2014), 356(7), 1527-1532, database is CAplus.

A new, catalytic methodol. for the synthesis of heterobiaryls by the ruthenium-catalyzed C-H activation/cross-coupling of heterocyclic amides with 2-aryl-1,3,2-dioxaborinanes is surveyed. From this survey, the highly regioselective reaction of furan-3-carboxamide to give 2-aryl-3-furanamides is optimized and generalized in scope with respect to the 2-aryl-1,3,2-dioxaborinane partners. E.g., in presence of RuH₂(CO)(PPh₃)₃ in toluene, reaction of N,N-diethylfuran-3-carboxamide with 2-aryl-1,3,2-dioxaborinane derivative (I) gave 92% heterobiaryl (II). Established thereby is a one-step synthetic method which may supercede the broadly applied two-step directed ortho metalation (DoM)-cross coupling reaction involving cryogenic and strong base conditions and which has potential for further ortho and remote metalation chem.

Advanced Synthesis & Catalysis published new progress about 530-40-5. 530-40-5 belongs to amides-buliding-blocks, auxiliary class Pyridine,Amine,Amide, name is N,N-Diethylisonicotinamide, and the molecular formula is C11H10N4, Formula: C10H14N2O.

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

Secatto, Adriana published the artcileThe leukotriene B4/BLT1 axis is a key determinant in susceptibility and resistance to histoplasmosis, Application In Synthesis of 321673-30-7, the publication is PLoS One (2014), 9(1), e85083/1-e85083/9, 9 pp., database is CAplus and MEDLINE.

The bioactive lipid mediator leukotriene B4(LTB4) greatly enhances phagocyte antimicrobial functions against a myriad of pathogens. In murine histoplasmosis, inhibition of the LT-generating enzyme 5-lipoxygenase (5-LO) increases the susceptibility of the host to infection. In this study, we investigated whether murine resistance or susceptibility to Histoplasma capsulatum infection is associated with leukotriene production and an enhancement of in vivo and/or in vitro antimicrobial effector function. We show that susceptible C57BL/6 mice exhibit a higher fungal burden in the lung and spleen, increased mortality, lower expression levels of 5-LO and leukotriene B4 receptor 1 (BLT1) and decreased LTB4 production compared to the resistant 129/Sv mice. Moreover, we demonstrate that endogenous and exogenous LTs are required for the optimal phagocytosis of H. capsulatum by macrophages from both murine strains, although C57BL/6 macrophages are more sensitive to the effects of LTB4 than 129/Sv macrophages. Therefore, our results provide novel evidence that LTB4 production and BLT1 signaling are required for a histoplasmosis-resistant phenotype.

PLoS One published new progress about 321673-30-7. 321673-30-7 belongs to amides-buliding-blocks, auxiliary class Immunology/Inflammation,Scavenger receptor, name is [(2-Hexylcyclopentylidene)amino]thiourea, and the molecular formula is C5H11NO2S, Application In Synthesis of 321673-30-7.

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

Aksinenko, A. Yu. published the artcileModification of phenothiazine and carbazole derivatives with trifluoromethyl-containing 1,3,5-oxadiazines and imidazolidinediones, Formula: C2H4ClNO, the publication is Russian Chemical Bulletin (2021), 70(11), 2180-2184, database is CAplus.

Modification of phenothiazine and carbazole derivatives with trifluoromethyl-containing 1,3,5-oxadiazines and imidazolidinediones based on the copper(I)-catalyzed alkyne-azide 1,3-cycloaddition was carried out.

Russian Chemical Bulletin published new progress about 79-07-2. 79-07-2 belongs to amides-buliding-blocks, auxiliary class Chloride,Amine,Aliphatic hydrocarbon chain,Amide,Inhibitor, name is 2-Chloroacetamide, and the molecular formula is C2H4ClNO, Formula: C2H4ClNO.

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

Peng, Yanqing published the artcileAmides by microwave-assisted dehydration of ammonium salts of carboxylic acids, Synthetic Route of 2447-79-2, the publication is Organic Preparations and Procedures International (2002), 34(1), 95-97, database is CAplus.

A direct and rapid procedure for the preparation of primary amides from ammonium salts of carboxylic acids in formamide under microwave irradiation is presented. Different types of carboxylic acids were converted to their corresponding amides by this procedure with satisfactory yields. The ammonium salts of carboxylic acids were formed in situ from ammonium bicarbonate and corresponding carboxylic acids. Formamide was suitable for this procedure both as a solvent and a dehydrating agent. This procedure compares favorably to other classical methods and it has the advantages of simple work-up, short reaction time, and the use of inexpensive and readily available reagents.

Organic Preparations and Procedures International published new progress about 2447-79-2. 2447-79-2 belongs to amides-buliding-blocks, auxiliary class Chloride,Amine,Benzene,Amide, name is 2,4-Dichlorobenzamide, and the molecular formula is C7H5Cl2NO, Synthetic Route of 2447-79-2.

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

Zhang, Zhichao published the artcileNovel soluble myeloid cell leukemia sequence 1 (Mcl-1) inhibitor (E,E)-2-(benzylaminocarbonyl)-3-styrylacrylonitrile (4g) developed using a fragment-based approach, HPLC of Formula: 15029-36-4, the publication is European Journal of Medicinal Chemistry (2013), 141-149, database is CAplus and MEDLINE.

Based on a known nanomolar Bcl-2 homol. domain 3 (BH3) mimetic 3-thiomorpholin-8-oxo-8H-acenaphtho[1,2-b] pyrrole-9-carbonitrile (I, MW: 331), we applied a fragment-based approach to obtain BH3 mimetics with improved affinity and improved solubility in a water-ethanol (9:1) cosolvent. After the deconstruction of I, we obtained fragment cyanoacetamide (II), which was determined to be a ligand efficiency (LE) hot part. After a rational optimization through fragment evolution beginning with fragment II, a smaller Mcl-1 inhibitor (E,E)-2-(benzylaminocarbonyl)-3-styrylacrylonitrile (III, MW: 288) with a 6-fold increase in affinity compared to I was obtained, as predicted by our optimization curve and identified by Mcl-1 protein NMR (NMR).

European Journal of Medicinal 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 C9H7NO2, HPLC of Formula: 15029-36-4.

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