Category: amides-buliding-blocks

Reference of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamideOn September 25, 1988 ,《Diastereoconversion of 1-alkynyl-2-aminoalkanols through oxazoline-2-ones with Sn2 type inversion of the hydroxy group》 was published in Chemical & Pharmaceutical Bulletin. The article was written by Kano, Shinzo; Yokomatsu, Tsutomu; Iwasawa, Haruo; Shibuya, Shiroshi. The article contains the following contents:

Treatment of (R,S)-RCCCH(OH)CHR1NHCO2CMe3 [R = Ph, R1 = Me, CH2Ph, CH2CHMe2; R = H(CH2)4, R1 = CH2CHMe2] with SOCl2 in Et2O at 0° gives the corresponding trans-oxazolidinones II (R2 = H) with isomerization. Conversion to II (R2 = CO2CMe3) followed by hydrolysis gives (S,S)-RCCCH(OH)CHR1NHCO2CMe3. The (S,S)-isomers are converted similarly to the (R,S)-isomers. After reading the article, we found that the author used (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Reference of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide)

(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) belongs to amides. Amides include many other important biological compounds, as well as many drugs like paracetamol, penicillin and LSD. Low-molecular-weight amides, such as dimethylformamide, are common solvents.Reference of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

《Zipped-up chain-type coordination polymers: unsymmetrical amide-containing ligands inducing β-sheet or helical structures》 was written by Uemura, Kazuhiro; Kumamoto, Yuki; Kitagawa, Susumu. Recommanded Product: 64479-78-3 And the article was included in Chemistry – A European Journal in 2008. The article conveys some information:

The crystal structures of thirteen AgI coordination polymers involving py-CONH-(CH2)n-py (py = pyridine; n = 0, 1) derivatives were determined by single-crystal x-ray analyses. All of the compounds form 1-dimensional chains composed of AgI atoms and bridging ligands {[Ag(py-CONH-(CH2)n-py)][X]}n (X = PF6-, ClO4-, BF4-, and NO3- with solvent mols.). The unsym. coordination environments around AgI atoms induce direction in the chains, i.e., -[NH-(CH2)n-py-Ag-py-CO]-, which resembles the alignment of amino acid chains in proteins. In {[Ag(4-pia)][X]}n (1 ⊃ X; 4-pia = N-(4-pyridyl)isonicotinamide; X = PF6-, ClO4-, BF4-, and NO3-), {[Ag(4-pmia)][X]}n (2 ⊃ X; 4-pmia = N-(pyridin-4-ylmethyl)isonicotinamide; X = PF6-, ClO4-·H2O, and NO3-·H2O), and {[Ag(3-pmia)][X]}n (3 ⊃ X; 3-pmia = N-(pyridin-3-ylmethyl)isonicotinamide; X = PF6-, ClO4-, BF4-, and NO3-·H2O), each chain is aligned parallel to neighboring chains, but adjacent chains run in the opposite direction. Particularly in {[Ag(3-pmia)]-[PF6]}n (3 ⊃ PF6-), {[Ag(3-pmia)][ClO4]}n (3 ⊃ ClO4-), and {[Ag(3-pmia)][BF4]}n (3 ⊃ BF4-), amide moieties of 3-pmia ligands are complementarily H bonded to amide moieties in neighboring chains, as in the β-sheet motif in proteins. However, in {[Ag(4-pmna)][PF6]·MeOH}n (4-pmna = N-(pyridin-4-ylmethyl)nicotinamide), all chains in the crystal form left-handed (4a ⊃ PF6-·MeOH) and right-handed (4b ⊃ PF6-·MeOH) helical structures with a helical pitch of 28 Å. Heterogeneous anion exchanges proceed reversibly in 2, but not in 3, which provides information about the thermal stabilities of the crystals. The results came from multiple reactions, including the reaction of N-(Pyridin-4-yl)isonicotinamide(cas: 64479-78-3Recommanded Product: 64479-78-3)

N-(Pyridin-4-yl)isonicotinamide(cas: 64479-78-3) belongs to amides. The solubilities of amides and esters are roughly comparable. Typically amides are less soluble than comparable amines and carboxylic acids since these compounds can both donate and accept hydrogen bonds.Recommanded Product: 64479-78-3

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

《Molecular Hydrogels from Bolaform Amino Acid Derivatives: A Structure-Properties Study Based on the Thermodynamics of Gel Solubilization》 was published in Chemistry – A European Journal in 2012. These research results belong to Nebot, Vicent J.; Armengol, Jose; Smets, Johan; Prieto, Susana Fernandez; Escuder, Beatriu; Miravet, Juan F.. COA of Formula: C11H9N3O The article mentions the following:

Insight is provided into the aggregation thermodn. associated with hydrogel formation by mol. gelators derived from L-valine and L-isoleucine. Solubility data from NMR measurements are used to extract thermodn. parameters for the aggregation in water. At room temperature and up to 55°C, these systems form self-assembled fibrillar networks in water with quite low or zero enthalpic component, whereas the entropy of the aggregation is favorable. These results are explained by considering that the hydrophobic effect is dominant in the self-assembly. However, studies by NMR and IR spectroscopy reveal that intermol. hydrogen bonding is also a key issue in the aggregation process of these mols. in water. The low enthalpy values measured for the self-assembly process are ascribed to the result of a compensation of the favorable intermol. hydrogen-bond formation and the unfavorable enthalpy component of the hydrophobic effect. Addnl., by using the hydrophobic character as a design parameter, enthalpy-controlled hydrogel formation, as opposed to entropy-controlled hydrogel formation, can be achieved in water if the gelator is polar enough. It is noteworthy that these two types of hydrogels, enthalpy- vs. entropy-driven hydrogels, present quite different response to temperature changes in properties such as the min. gelator concentration or the rheol. moduli. Finally, the presence of a polymorphic transition in a hydrogel upon heating above 70°C is reported and ascribed to the weakening of the hydrophobic effect upon heating. The new soft polymorphic materials present dramatically different solubility and rheol. properties. Altogether these results are aimed to contribute to the rational design of mol. hydrogelators, which could be used for the tailored preparation of this type of soft materials. The reported results could also provide ground for the rationale of different self-assembly processes in aqueous media. The experimental process involved the reaction of N-(Pyridin-4-yl)isonicotinamide(cas: 64479-78-3COA of Formula: C11H9N3O)

N-(Pyridin-4-yl)isonicotinamide(cas: 64479-78-3) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole.COA of Formula: C11H9N3O The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors. In primary and secondary amides, the presence of N–H dipoles allows amides to function as H-bond donors as well.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

《Design and synthesis of tripeptidyl furylketones as selective inhibitors against the β5 subunit of human 20S proteasome》 was written by Sun, Qi; Zhou, Tongliang; Xi, Dandan; Li, Xiaona; Lu, Zirui; Xu, Fengrong; Wang, Chao; Niu, Yan; Xu, Ping. Product Details of 87694-50-6 And the article was included in European Journal of Medicinal Chemistry on April 15 ,2020. The article conveys some information:

A series of tripeptidic proteasome inhibitors with furylketone as C-terminus were designed and synthesized. Biochem. evaluations against β1, β2 and β5 subunits revealed that they acted selectively on β5 subunit with IC50s against chymotrypsin-like (CT-L) activity in micromolar range. LC-MS/MS anal. of the ligand-20S proteasome mixture showed that the most potent compound (I) (IC50 = 0.18μM) made no covalent modification on 20S proteasome. However, it was identified acting in a slowly reversible manner in wash-out assay and the reversibility was much lower than that of MG132, suggesting the possibility of these tripeptidic furylketones forming reversible covalent bonds with 20S proteasome. Several compounds were selected for anti-proliferative assay towards multiple cancer cell lines, and compound I displayed comparable potency to pos. control (MG132) in all cell lines tested. Furthermore, the pharmacokinetic (PK) data in rats indicated I behaved similarly (Cmax, 2007μg/L; AUC0-t, 680μg/L·h; Vss, 0.66 L/kg) to the clin. used agent carfilzomib. All these data suggest I is a good lead compound to be developed to novel anti-tumor agent. The experimental process involved the reaction of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Product Details of 87694-50-6)

(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole. The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors.Product Details of 87694-50-6 In primary and secondary amides, the presence of N–H dipoles allows amides to function as H-bond donors as well.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 683-57-8In 2020 ,《Chemical synthesis of an enzyme containing an artificial catalytic apparatus》 was published in Australian Journal of Chemistry. The article was written by Torbeev, Vladimir; Kent, Stephen B. H.. The article contains the following contents:

With the goal of investigating electronic aspects of the catalysis of peptide bond hydrolysis, an analog of HIV-1 protease was designed in which a non-peptide hydroxy-isoquinolinone artificial catalytic apparatus replaced the conserved Asp25-Thr26-Gly27 sequence in each 99-residue polypeptide chain of the homodimeric enzyme mol. The enzyme analog was prepared by total chem. synthesis and had detectable catalytic activity on known HIV-1 protease peptide substrates. Compared with uncatalyzed hydrolysis, the analog enzyme increased the rate of peptide bond hydrolysis by ∼108-fold. Extensions of this unique approach to the study of enzyme catalysis in HIV-1 protease are discussed. In the experiment, the researchers used 2-Bromoacetamide(cas: 683-57-8Application of 683-57-8)

2-Bromoacetamide(cas: 683-57-8) can be used in preparation of (2-carbamoylmethoxy-5-chloro-benzyl)-carbamic acid tert-butyl ester. It was aslo used as precursor to dehydropeptidase I inactivator.Application of 683-57-8

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics