Category: amides-buliding-blocks

In 2011,LaMarche, Matthew J.; Leeds, Jennifer A.; Amaral, Kerri; Brewer, Jason T.; Bushell, Simon M.; Dewhurst, Janetta M.; Dzink-Fox, JoAnne; Gangl, Eric; Goldovitz, Julie; Jain, Akash; Mullin, Steve; Neckermann, Georg; Osborn, Colin; Palestrant, Deborah; Patane, Michael A.; Rann, Elin M.; Sachdeva, Meena; Shao, Jian; Tiamfook, Stacey; Whitehead, Lewis; Yu, Donghui published 《Antibacterial optimization of 4-aminothiazolyl analogues of the natural product GE2270 A: Identification of the cycloalkylcarboxylic acids》.Journal of Medicinal Chemistry published the findings.Application of 71432-55-8 The information in the text is summarized as follows:

4-Aminothiazolyl analogs of the antibiotic natural product GE2270 A were designed, synthesized, and optimized for their activity against Gram pos. bacterial infections. Optimization efforts focused on improving the physicochem. properties (e.g., aqueous solubility and chem. stability) of the 4-aminothiazolyl natural product template while improving the in vitro and in vivo antibacterial activity. Structure-activity relationships were defined, and the solubility and efficacy profiles were improved over those of previous analogs and GE2270 A. These studies identified novel, potent, soluble, and efficacious elongation factor-Tu inhibitors, which bear cycloalkylcarboxylic acid side chains, and culminated in the selection of development candidates amide (I) (R1 = C:O) and urethane I (R1 = OC:O). In addition to this study using tert-Butyl N,N’-diisopropylcarbamimidate, there are many other studies that have used tert-Butyl N,N’-diisopropylcarbamimidate(cas: 71432-55-8Application of 71432-55-8) was used in this study.

tert-Butyl N,N’-diisopropylcarbamimidate(cas: 71432-55-8) belongs to anime. The reaction of alkyl halides, R―X, where X is a halogen, or analogous reagents with ammonia (or amines) is useful with certain compounds. Not all alkyl halides are effective reagents; the reaction is sluggish with secondary alkyl groups and fails with tertiary ones. Its usefulness is largely confined to primary alkyl halides (those having two hydrogen atoms on the reacting site).Application of 71432-55-8

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

《The chemistry of N-substituted benzotriazoles. Part 20. Mono-N-tert-butylation of aromatic and heteroaromatic amines》 was published in Journal of the Chemical Society in 1989. These research results belong to Katritzky, Alan R.; Vanden Eynde, Jean Jacques. Related Products of 70298-88-3 The article mentions the following:

Adducts R1CH(1-benzotriazolyl)NHR2, (R1 = Pr, CHMe2, CMe3, R2 = 2-, 3-pyridyl, Ph, 4-methyl-2-pyridyl, 5-chloro-2-pyridyl, 3-ClC6H4, 3-, 4-O2NC6H4), readily available from aldehydes, primary aromatic or heteroaromatic amines, and benzotriazole are converted by H2O2-SeO2 into mixtures of R1CONHR2 and HCONR1R2 in proportions which depend rationally on the nature of the R1 group. For R1 = CMe3, the formamide Me3CNR2CHO is formed in satisfactory yields, thus enabling the title reaction to be achieved. After reading the article, we found that the author used 2,2-Dimehtyl-N-pyridin-3-yl-propionamide(cas: 70298-88-3Related Products of 70298-88-3)

2,2-Dimehtyl-N-pyridin-3-yl-propionamide(cas: 70298-88-3) belongs to anime.Typically the presence of an amine functional group is deduced by a combination of techniques, including mass spectrometry as well as NMR and IR spectroscopies. 1H NMR signals for amines disappear upon treatment of the sample with D2O. In their infrared spectrum primary amines exhibit two N-H bands, whereas secondary amines exhibit only one.Related Products of 70298-88-3

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

Tao, Ming; Bihovsky, Ron; Kauer, James C. published their research in Bioorganic & Medicinal Chemistry Letters on December 17 ,1996. The article was titled 《Inhibition of calpain by peptidyl heterocycles》.Product Details of 87694-50-6 The article contains the following contents:

Dipeptidyl and tripeptidyl heterocycles designed to mimic peptide ketoamides and ketoacids were prepared and evaluated in vitro as inhibitors of human calpain I. For example, Boc-Leu-Leu-imidazole, I, inhibited calpain I at low micromolar concentrations In the part of experimental materials, we found many familiar compounds, such as (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.Product Details of 87694-50-6 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.

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

Miletin, Miroslav; Dolezal, Martin; Opletalova, Veronika; Hartl, Jiri; Kral’ova, Katarina; Machacek, Milos published an article in Molecules [online computer file]. The title of the article was 《Some anilides of 2-alkylthio- and 2-chloro-6-alkylthio-4-pyridinecarboxylic acids: synthesis and photosynthesis-inhibiting activity》.Computed Properties of C6H4Cl2N2O The author mentioned the following in the article:

Many compounds containing a -CONH- group display photosynthesis-inhibiting activity. Based on this structural feature, a group of anilides of 2-alkylthio- (I) or 2-chloro-6-alkylthio-4-pyridinecarboxylic acids (II) was synthesized. The prepared compounds were tested for their inhibition of the oxygen evolution rate (OER) in spinach chloroplasts. A quasi-parabolic dependence between photosynthesis-inhibiting activity and the lipophilicity of the compounds was determined The inhibitory activity of compounds I was higher than that of II for comparable lipophilicity values. The results came from multiple reactions, including the reaction of 2,6-Dichloroisonicotinamide(cas: 89281-13-0Computed Properties of C6H4Cl2N2O)

2,6-Dichloroisonicotinamide(cas: 89281-13-0) belongs to anime. Acylation is one of the most important reactions of primary and secondary amines; a hydrogen atom is replaced by an acyl group (a group derived from an acid, such as RCOOH or RSO3H, by removal of ―OH, such as RC(=O)―, RS(O)2―, and so on). Reagents may be acid chlorides (RCOC1, RSO2C1), anhydrides ((RCO)2O), or even esters (RCOOR′); the products are amides of the corresponding acids.Computed Properties of C6H4Cl2N2O

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

Lawson, Edward C.; Santulli, Rosemary J.; Dyatkin, Alexey B.; Ballentine, Scott A.; Abraham, William M.; Rudman, Sandra; Page, Clive P.; de Garavilla, Lawrence; Damiano, Bruce P.; Kinney, William A.; Maryanoff, Bruce E. published an article in Bioorganic & Medicinal Chemistry. The title of the article was 《Selection of a 2-azabicyclo[2.2.2]octane-based α4β1 integrin antagonist as an inhaled anti-asthmatic agent》.Category: amides-buliding-blocks The author mentioned the following in the article:

The α4β1 integrin, expressed on eosinophils and neutrophils, induces inflammation in the lung by facilitating cellular infiltration and activation. From a number of potent α4β1 antagonists that the authors evaluated for safety and efficacy, compound (I) was selected as a lead candidate for antiasthma therapy by the inhalation route. The authors devised an optimized stereoselective synthesis to facilitate the preparation of a sufficiently large quantity of I for assessment in vivo. Administration of I to allergen-sensitive sheep by inhalation blocked the late-phase response of asthma and abolished airway hyper-responsiveness at 24 h following the antigen challenge. Addnl., the recruitment of inflammatory cells into the lungs was inhibited. Administration of I to ovalbumin-sensitized guinea pigs i.p. blocked airway resistance and inhibited the recruitment of inflammatory cells. The experimental part of the paper was very detailed, including the reaction process of 2,6-Dichloroisonicotinamide(cas: 89281-13-0Category: amides-buliding-blocks)

2,6-Dichloroisonicotinamide(cas: 89281-13-0) belongs to anime. Acylation is one of the most important reactions of primary and secondary amines; a hydrogen atom is replaced by an acyl group (a group derived from an acid, such as RCOOH or RSO3H, by removal of ―OH, such as RC(=O)―, RS(O)2―, and so on). Reagents may be acid chlorides (RCOC1, RSO2C1), anhydrides ((RCO)2O), or even esters (RCOOR′); the products are amides of the corresponding acids.Category: amides-buliding-blocks

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

In 2011,Angewandte Chemie, International Edition included an article by Zhang, Min; Imm, Sebastian; Baehn, Sebastian; Neumann, Helfried; Beller, Matthias. Recommanded Product: 2-Hydroxy-N-phenylacetamide. The article was titled 《Synthesis of α-amino acid amides: ruthenium-catalyzed amination of α-hydroxy amides》. The information in the text is summarized as follows:

An efficient ruthenium-catalyzed amination of α-hydroxy acid derivatives is reported. Using a variety of amines, including anilines, primary and secondary aliphatic amines, and ammonia, a wide range of amino acid amides was obtained from α-hydroxy amides or esters. Combination of Ru3(CO)12 and 1,2-bis(dicyclohexylphosphino)ethane was the best catalyst system. In the experiment, the researchers used many compounds, for example, 2-Hydroxy-N-phenylacetamide(cas: 4746-61-6Recommanded Product: 2-Hydroxy-N-phenylacetamide)

2-Hydroxy-N-phenylacetamide(cas: 4746-61-6) 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.Recommanded Product: 2-Hydroxy-N-phenylacetamide 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

Fu, Yiqiu; Xu, Bo; Zou, Xiaomin; Ma, Chao; Yang, Xiaoming; Ke, Mou; Fu, Gang; Yang, Lue; Xu, Ping published an article on February 15 ,2007. The article was titled 《Design and synthesis of a novel class of furan-based molecules as potential 20S proteasome inhibitors》, and you may find the article in Bioorganic & Medicinal Chemistry Letters.Electric Literature of C13H26N2O4 The information in the text is summarized as follows:

A class of furan-based compounds as potential 20S proteasome inhibitors have been designed and synthesized, among which nine compounds are peptide derivatives and six mols. are statine peptidomimetics. The C-terminal furanyl moiety was introduced to target mols. as furan-based amino acids. All the compounds were obtained steadily with moderate to high yield. Compound I was a selective moderate potent proteasome peptidomimetic inhibitor. It inhibited HepG2 and HL-60 proliferation effectively. In the experiment, the researchers used many compounds, for example, (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Electric Literature of C13H26N2O4)

(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) belongs to amides.Electric Literature of C13H26N2O4 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.

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

Recommanded Product: 87694-50-6On September 12, 2018 ,《Defining the Determinants of Specificity of Plasmodium Proteasome Inhibitors》 was published in Journal of the American Chemical Society. The article was written by Yoo, Euna; Stokes, Barbara H.; de Jong, Hanna; Vanaerschot, Manu; Kumar, T. R. S.; Lawrence, Nina; Njoroge, Mathew; Garcia, Arnold; Van der Westhuyzen, Renier; Momper, Jeremiah D.; Ng, Caroline L.; Fidock, David A.; Bogyo, Matthew. The article contains the following contents:

The Plasmodium proteasome is an emerging antimalarial target due to its essential role in all the major life cycle stages of the parasite and its contribution to the establishment of resistance to artemisinin (ART)-based therapies. However, because of a similarly essential role for the host proteasome, the key property of any antiproteasome therapeutic is selectivity. Several parasite-specific proteasome inhibitors have recently been reported, however, their selectivity must be improved to enable clin. development. Here we describe screening of diverse libraries of non-natural synthetic fluorogenic substrates to identify determinants at multiple positions on the substrate that produce enhanced selectivity. We find that selection of an optimal electrophilic “”warhead”” is essential to enable high selectivity that is driven by the peptide binding elements on the inhibitor. We also find that host cell toxicity is dictated by the extent of coinhibition of the human β2 and β5 subunits. Using this information, we identify compounds with over 3 orders of magnitude selectivity for the parasite enzyme. Optimization of the pharmacol. properties resulted in mols. that retained high potency and selectivity, were soluble, sufficiently metabolically stable and orally bioavailable. These mols. are highly synergistic with ART and can clear parasites in a mouse model of infection, making them promising leads as antimalarial drugs.(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Recommanded Product: 87694-50-6) was used in this study.

(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) 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: 87694-50-6

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

SDS of cas: 87694-50-6On November 15, 2021 ,《Structure-activity relationship study of hydroxyethylamine isostere and P1′ site structure of peptide mimetic BACE1 inhibitors》 appeared in Bioorganic & Medicinal Chemistry. The author of the article were Kobayashi, Kazuya; Otani, Takuya; Ijiri, Saki; Kawasaki, Yuki; Matsubara, Hiroki; Miyagi, Takahiro; Kitajima, Taishi; Iseki, Risa; Ishizawa, Katsuyasu; Shindo, Naoka; Okawa, Kouta; Ueda, Kouta; Ando, Syun; Kawakita, Momoka; Hattori, Yasunao; Akaji, Kenichi. The article conveys some information:

An aromatic substituent has been introduced into a known hydroxyethylamine (HEA)-type BACE1 inhibitor containing the superior substrate sequence to enhance inhibitory activity. The HEA-type isosteres bearing different hydroxyl group and Me group configurations were prepared through a branched synthesis approach using intra- and inter-mol. epoxide opening reactions. The effect of their configuration was evaluated, showing that an R-configuration improved the inhibitory activity, while introduction of a Me group on the isostere decreased the activity. Based on the non-substituted isostere with an R-configuration, 21 derivatives containing various substituents at the P1′ site were synthesized. Our evaluation of the derivatives showed that the structure of the P1′ site had a clear effect on activity, and highly potent inhibitor 40g, which showed sub-micromolar activity against recombinant BACE1 (rBACE1), was identified. The docking simulation of 40g with rBACE1 suggested that a carboxymethyl group at the para-position of the P1′ benzene ring interacted with Lys285 in the S1′ pocket. The results came from multiple reactions, including the reaction of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6SDS of cas: 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.SDS of cas: 87694-50-6 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

Name: (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamideOn March 31, 2012, Mallik, Shyam Kumar; Li, Da Yu; Cui, Minghua; Song, Hyun-Ok; Park, Hyun; Kim, Hak Sung published an article in Archives of Pharmacal Research. The article was 《Synthesis and evaluation of peptidyl α,β-unsaturated carbonyl derivatives as anti-malarial calpain inhibitors》. The article mentions the following:

Malarial calpain is a cysteine protease believed to be a central mediator essential for parasitic activities. N-Acetyl-L-leucyl-L-leucyl-L-norleucinal (ALLN), a calpain inhibitor, showed an excellent inhibitory effect on the erythrocytic stages of Plasmodium falciparum. However the aldehyde group of ALLN makes it susceptible to metabolism Therefore, we designed α,β-unsaturated carbonyl peptides that could serve as electrophiles for cysteine residues in calpain. Among the synthetic analogs based on the structure of ALLN, peptidyl esters (I) (R1 = i-Bu, R2 = Boc, Cbz; R1 = Ph, R2 = Cbz; Boc = tert-butoxycarbonyl, Cbz = benzyloxycarbonyl) showed the most potent anti-malarial effects, with the same IC50 values of 5.0 μM. Also they showed the high selective toxicity for the malaria vs. Hela cell with 40.6, 69.2 and 24.3 fold for I (R1 = i-Bu, R2 = Boc, Cbz; R1 = Ph, R2 = Cbz) resp. Dipeptidyl α,β-unsaturated carbonyl derivatives consisting of two amino acids gave better anti-malarial effects than those consisting with one amino acid. The fluctuation in anti-malarial activity with small changes in chem. structure indicates the possibilities of improving synthetic analogs. In the experiment, the researchers used many compounds, for example, (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Name: (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. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole.Name: (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide 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