Category: 87694-50-6

Sin, Ny; Kim, Kyung Bo; Elofsson, Mikael; Meng, Lihao; Auth, Hak; Kwok, Benjamin H. B.; Crews, Craig M. published their research in Bioorganic & Medicinal Chemistry Letters on August 2 ,1999. The article was titled 《Total synthesis of the potent proteasome inhibitor epoxomicin: a useful tool for understanding proteasome biology》.Formula: C13H26N2O4 The article contains the following contents:

Epoxomicin (I), a peptide α’,β’-epoxy-ketone isolated from the actinomycete strain NumberQ996-17, possesses potent in vivo anti-tumor and anti-inflammatory activities. The authors report the first syntheses of I, [3H]-I , and a biotinylated I analog as well as the absolute configuration of the epoxide stereo-center. The natural product and derivatives have permitted the first identification of the proteasome as the specific cellular target of I. In the experimental materials used by the author, we found (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Formula: C13H26N2O4)

(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) belongs to amides.Formula: C13H26N2O4Amides are pervasive in nature and technology. Proteins and important plastics like Nylons, Aramid, Twaron, and Kevlar are polymers whose units are connected by amide groups (polyamides); these linkages are easily formed, confer structural rigidity, and resist hydrolysis.

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

Related Products of 87694-50-6On March 4, 2020, Schwartz, Brett D.; Zhang, Meng Yao; Attard, Riley H.; Gardiner, Michael G.; Malins, Lara R. published an article in Chemistry – A European Journal. The article was 《Structurally Diverse Acyl Bicyclobutanes: Valuable Strained Electrophiles》. The article mentions the following:

This work reported two efficient pathways for the rapid preparation of over 20 structurally diverse bicyclo[1.1.0]butane (BCB) ketones, such as I [R = cuban-1-yl, BOCHNCH2, 4-MeOC6H4, etc.] encompassing simple alkyl and aryl derivatives, as well as unprecedented amino acid, dipeptide, bioisostere, and bifunctional linchpin reagents currently inaccessible using literature methods. Analogs were readily forged in two steps and in high yields from simple carboxylic acids or through unsym. ketone synthesis beginning with a convenient carbonyl dication equivalent The utility of this novel toolbox of strained electrophiles for selective modification of proteinogenic nucleophiles was highlighted. The results came from multiple reactions, including the reaction of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Related Products 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.Related Products of 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

HPLC of Formula: 87694-50-6On October 1, 2014 ,《Semi-synthesis of biologically active nisin hybrids composed of the native lanthionine ABC-fragment and a cross-stapled synthetic DE-fragment》 was published in Bioorganic & Medicinal Chemistry. The article was written by Slootweg, Jack C.; Peters, Nienke; Quarles van Ufford, H. C.; Breukink, Eefjan; Liskamp, Rob M. J.; Rijkers, Dirk T. S.. The article contains the following contents:

The antimicrobial peptide nisin is a promising template for designing novel peptide-based antibiotics to improve its drug-like properties. First steps in that direction represent the synthesis of hybrid nisin derivatives that contain a native nisin ABC-part and synthesized cross-stapled DE-ring fragments and are described here. The biol. activity of the newly synthesized nisin derivatives was evaluated in order to compare the bioactivity of the synthetic DE-ring containing mimic and native lanthionine-bridged DE-ring containing nisin. The native nisin ABC-ring system was obtained via chymotrypsin digestion of full-length nisin, and was subsequently functionalized at the C-terminal carboxylate with two different amino alkyne moieties. Next, nisin hybrids were successfully prepared using Cu(I)-catalyzed azide alkyne cycloaddition ‘click’ chem. by chemo-selective ligation of the ABC-alkyne with the N-terminal azido functionalized dicarba-DE ring mimic. The newly synthesized compounds were active as potent lipid II binders and retained antimicrobial activity in a growth inhibition assay. However, pore formation was not observed, possibly either due to the different character of the ‘staples’ as compared to the parent sulfides, or due to the triazole moiety as a sub-optimal amide bond isostere. In the experiment, the researchers used many compounds, for example, (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6HPLC of Formula: 87694-50-6)

(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) belongs to amides.HPLC of Formula: 87694-50-6Amides are pervasive in nature and technology. Proteins and important plastics like Nylons, Aramid, Twaron, and Kevlar are polymers whose units are connected by amide groups (polyamides); these linkages are easily formed, confer structural rigidity, and resist hydrolysis.

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

《Preparation of Weinreb amides using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM)》 was written by Hioki, Kazuhito; Kobayashi, Hiroko; Ohkihara, Rumi; Tani, Shohei; Kunishima, Munetaka. Synthetic Route of C13H26N2O4 And the article was included in Chemical & Pharmaceutical Bulletin on April 30 ,2004. The article conveys some information:

Weinreb amides were successfully prepared from the corresponding carboxylic acids by using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) as a coupling reagent to form the activated ester, which then, reacted with N,O-dimethylhydroxylamine·HCl to form the amide. Methanol, iso-propanol and acetonitrile were useful solvents for the reaction because they solubilized DMT-MM. Weinreb amides of PhCO2H, 4-ClC6H4CO2H, PhCH:CHCO2H, PhCH(Me)CO2H, Cbz-Gly-OH, Boc-Leu-OH, Boc-Trp-OH, Boc-Pro-OH, PhCOCO2H and EtO2C(CH2)4CO2H were synthesized in moderate to very high yields.(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Synthetic Route of C13H26N2O4) was used in this study.

(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.Synthetic Route of C13H26N2O4 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

Pehere, Ashok D.; Nguyen, Steven; Garlick, Sarah K.; Wilson, Danny W.; Hudson, Irene; Sykes, Matthew J.; Morton, James D.; Abell, Andrew D. published an article on January 15 ,2019. The article was titled 《Tripeptide analogues of MG132 as protease inhibitors》, and you may find the article in Bioorganic & Medicinal Chemistry.Synthetic Route of C13H26N2O4 The information in the text is summarized as follows:

The 26S proteasome and calpain are linked to a number of important human diseases. Here, we report a series of analogs of the prototypical tripeptide aldehyde inhibitor MG132 that show a unique combination of high activity and selectivity for calpains over proteasome. Tripeptide aldehydes (1-3) with an aromatic P3 substituent show enhanced activity and selectivity against ovine calpain 2 relative to chymotrypsin-like activity of proteasome. Docking studies reveal the key contacts between inhibitors and calpain to confirm the importance of the S3 pocket with respect to selectivity between calpains 1 and 2 and the proteasome.(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Synthetic Route of C13H26N2O4) was used in this study.

(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.Synthetic Route of C13H26N2O4

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

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

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

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

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