Category: 87694-50-6

Zhang, Wen; Wang, Xueyuan; Zhang, Haoyang; Wen, Tiantian; Yang, Lin; Miao, Hang; Wang, Jia; Liu, Hailong; Yang, Xu; Lei, Meng; Zhu, Yongqiang published an article in Bioorganic & Medicinal Chemistry. The title of the article was 《Discovery of novel tripeptide propylene oxide proteasome inhibitors for the treatment of multiple myeloma》.COA of Formula: C13H26N2O4 The author mentioned the following in the article:

The ubiquitin proteasome pathway (UPP) plays a critical role in the maintenance of cell homeostasis and the development of diseases, such as cancer and neurodegenerative disease. A series of novel tripeptide propylene oxide compounds as proteasome inhibitors were designed, synthesized and biol. investigated in this manuscript. The enzymic activities of final compounds against 20S human proteasome were investigated and structure-activity relationship (SAR) was summarized. Some potent compounds were further evaluated to inhibit the proliferation of multiple myeloma (MM) cancer cell lines RPMI8226 and U266B. The results showed that some compounds were active against MM cancer cell lines with IC50 values of less than 50 nM. The microsomal metabolic stabilities in human, rat and mice species were carried out and the results showed that compounds (I) (R1 = iso-Bu, Bn) were stable enough to be in vivo investigated. The in vivo pharmacokinetic results showed that compounds I (R1 = iso-Bu, Bn) had acceptable biol. parameters for both ig and iv administrations. In vivo antitumor activities of compounds I (R1 = iso-Bu, Bn) with the doses of 100 mg/kg and 50 mg/kg BIW were performed by using RPMI8226 xenograft nude mouse model. Toxicities of compounds I (R1 = iso-Bu, Bn) were not observed during the experiment and dose dependent effect was obvious and the tumor volume was greatly inhibited. In addition to this study using (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide, there are many other studies that have used (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6COA of Formula: C13H26N2O4) was used in this study.

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

In 2014,Organic & Biomolecular Chemistry included an article by Xin, Bo-Tao; de Bruin, Gerjan; Verdoes, Martijn; Filippov, Dmitri V.; van der Marel, Gijs A.; Overkleeft, Herman S.. Recommanded Product: 87694-50-6. The article was titled 《Exploring dual electrophiles in peptide-based proteasome inhibitors: carbonyls and epoxides》. The information in the text is summarized as follows:

Peptide epoxyketones are potent and selective proteasome inhibitors. Selectivity is governed by the epoxyketone dual electrophilic warhead, which reacts with the N-terminal threonine 1,2-amino alc. uniquely present in proteasome active sites. We studied a series of C-terminally modified oligopeptides featuring adjacent electrophiles based on the epoxyketone warhead. We found that the carbonyl moiety in the natural warhead is essential, but that the adjacent epoxide can be replaced by a carbonyl, though with considerable loss of activity. The results came from multiple reactions, including the reaction of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Recommanded Product: 87694-50-6)

(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) belongs to amides.Recommanded Product: 87694-50-6 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

Related Products of 87694-50-6On March 31, 1999, Falkiewicz, Bogdan; Kowalska, Katarzyna; Kolodziejczyk, Aleksandra S.; Wisniewski, Kaximierz; Lankiewicz, Leszek published an article in Nucleosides & Nucleotides. The article was 《Synthesis of new chiral peptide nucleic acid (PNA) monomers by a simplified reductive amination method》. The article mentions the following:

The aim of this work was the preparation of four new peptide nucleic acid (PNA) monomers, e.g. I [R = iso-Bu, CH2Ph, (R)-CH(OCH2Ph)CH3, CH2C6H4-4-OCH2Ph; Boc = Me3CO2C] by reductive amination of Nα-Boc-protected chiral amino aldehydes, derived from Leu, Phe, Tyr(Bzl), and Thr(Bzl), with Me glycinate. To the crude 2-substituted Me N-(2-Boc-aminoethyl)glycinates obtained, thymin-1-ylacetic acid was coupled using TBTU procedure in a one-pot reaction. PNA monomers were isolated and characterized. In the experiment, the researchers used (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.Related Products of 87694-50-6 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

In 1985,Journal of Medicinal Chemistry included an article by Martinez, Jean; Bali, Jean Pierre; Rodriguez, Marc; Castro, B.; Magous, R.; Laur, Jeanine; Lignon, Marie Francoise. Recommanded Product: 87694-50-6. The article was titled 《Synthesis and biological activities of some pseudo-peptide analogs of tetragastrin: the importance of the peptide backbone》. The information in the text is summarized as follows:

Title pseudo-peptide analogs I (Boc = Me3CO2C, R = H) (II), Boc-Trp-NHCH(CH2CHMe2)CH2-Asp-Phe-NH2 (III), and Boc-Trp-Leu-NHCH(CH2CO2H)CH2-Phe-NH2 (IV) were prepared by conventional solution methods. Thus, Boc-Trp-OH was condensed with MeONHMe.HCl by DCC to give Boc-TrpN(OMe)Me, which was reduced by LiAlH4 to give tryptophanal V. R1-Leu-Asp(OCH2Ph)-Phe-NH2 (VI, R1 = Boc) was prepared and then Boc-deblocked to give VI (R1 = H), which was treated with V in the presence of NaBH3CN to give I (R = CH2Ph), which was debenzylated by hydrogenolysis to give II. III was prepared similarly from Boc-Trp-NHCH(CH2CHMe2)CHO and H-Asp(OCH2Ph)-Phe-NH2, whereas PhCH2O2CNHCH(CH2CO2CMe3)CHO was prepared and used in the synthesis of IV. II and III have the same affinity as tetragastrin (VII) for gastrin receptor on isolated mucosal cells, whereas IV exhibited lower affinity. The acid secretion-stimulating activity of I in rats was identical to that of VII; III did not exhibit agonist activity but was able to antagonize the action of gastrin. In the experiment, the researchers used many compounds, for example, (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Recommanded Product: 87694-50-6)

(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) belongs to amides.Recommanded Product: 87694-50-6 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

In 2010,Chemistry – A European Journal included an article by Tietze, Daniel; Tischler, Marco; Voigt, Stephan; Imhof, Diana; Ohlenschlaeger, Oliver; Goerlach, Matthias; Buntkowsky, Gerd. HPLC of Formula: 87694-50-6. The article was titled 《Development of a Functional cis-Prolyl Bond Biomimetic and Mechanistic Implications for Nickel Superoxide Dismutase》. The information in the text is summarized as follows:

During recent years several peptide-based Ni superoxide dismutase (NiSOD) models have been developed. These NiSOD models show an important structural difference compared to the native NiSOD enzyme, which could cause a completely different mechanism of superoxide dismutation. In the native enzyme the peptide bond between Leu4 and Pro5 is cis-configured, while the NiSOD models exhibit a trans-configured peptide bond between these two residues. To shed light on how the configuration of this single peptide bond influences the activity of the NiSOD model peptides, a new cis-prolyl bond surrogate was developed. As surrogate we chose a leucine/alanine-based disubstituted 1,2,3-triazole, which was incorporated into the NiSOD model peptide replacing residues Leu4 and Pro5. The yielded 1,5-disubstituted triazole nickel peptide exhibited high SOD activity, which was approx. the same activity as its parent trans-configured analog. Hence, the conformation of the prolyl peptide bond apparently has of minor importance for the catalytic activity of the metallopeptides as postulated in literature. Furthermore, it is shown that the triazole metallopeptide is forming a stable cyanide adduct as a substrate analog model complex. The results came from multiple reactions, including the reaction of (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: 87694-50-6 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

Application In Synthesis of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamideOn September 16, 1988 ,《Synthesis of the dipeptide hydroxyethylene isostere of Leu-Val, a transition state mimic for the control of enzyme function》 was published in Journal of Organic Chemistry. The article was written by Wuts, Peter G. M.; Putt, Sterling R.; Ritter, Allen R.. The article contains the following contents:

Dipeptide isosteres mimic the transition states of proteolytic enzymes or alter or enhance the function of regulatory peptides. A general approach was developed that may be used to prepare a diverse array of dipeptide hydroxyethylene isosteres. Thus, a mimic of Leu-Val, the cleavage site of the enzyme renin, was prepared The sequence begins with addition of CH2:CHMgBr to leucinal derivative Boc-Leu-H (Boc = Me3CO2C) to form the corresponding allylic alc. This is converted to the acetonide, ozonized, and equilibrated to give the trans aldehyde I (R = CHO) as the primary product. A Wadsworth-Emmons olefination, followed by hydrogenation, affords the ester I [R = CH2CH(CHMe2)CO2Et] as a mixture of isomers. Hydrolysis of the acetonide and purification gives the desired lactone II in 23% overall yield from Boc-leucinol. The results came from multiple reactions, including the reaction of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Application In Synthesis 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.Application In Synthesis of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamideAmides 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

Electric Literature of C13H26N2O4On November 30, 2014 ,《Design, Synthesis and Biological Evaluation of Peptidyl Epoxyketone Proteasome Inhibitors Composed of β-amino Acids》 appeared in Chemical Biology & Drug Design. The author of the article were Zhang, Jiankang; Han, Mengmeng; Ma, Xiaodong; Xu, Lei; Cao, Jiayi; Zhou, Yubo; Li, Jia; Liu, Tao; Hu, Yongzhou. The article conveys some information:

A series of novel di- and tripeptidyl epoxyketone derivatives composed of β-amino acids were designed, synthesized and evaluated for their proteasome inhibitory activities and antiproliferation activities against two multiple myeloma cell lines RPMI 8226 and NCI-H929 and normal cells (peripheral blood mononucleated cells). Among these tested compounds, tripeptidyl analogs showed much more potent activities than dipeptides, and four tripeptidyl compounds exhibited proteasome inhibitory activities with IC50 values ranging from 0.97±0.05 to 1.85±0.11 μm. In addition, all the four compounds showed antiproliferation activities with IC50 values at low micromolar levels against two multiple myeloma cell lines and weak activities against normal cells. Furthermore, Western blot anal. was performed to verify the proteasome inhibition induced by compounds I [R = 4-FC6H4] and I [R = 4-MeOC6H4]. All the exptl. results validated that the β-amino acid building block has the potential for the development of proteasome inhibitors. In addition to this study using (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide, there are many other studies that have used (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Electric Literature of C13H26N2O4) was used in this study.

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

Formula: C13H26N2O4On October 14, 1994 ,《Influence of Lipophilicity on the Biological Activity of Cyclic Pseudopeptide NK-2 Receptor Antagonists》 was published in Journal of Medicinal Chemistry. The article was written by Quartara, Laura; Fabbri, Gaetano; Ricci, Renzo; Patacchini, Riccardo; Pestellini, Vittorio; Maggi, Carlo Alberto; Pavone, Vincenzo; Giachetti, Antonio; Arcamone, Federico. The article contains the following contents:

A series of cyclic pseudopeptides cyclo(Leuψ[CH2NH]Xaa-Gln-Trp-Phe-β-Ala) (I; Xaa = α-amino acid residue), was prepared to establish the role of the Xaa side chain for tachykinin NK-2 receptor antagonist activity. Syntheses have been carried out in solid phase with either 9-fluorenylmethoxycarbonyl (Fmoc) or tert-butoxycarbonyl (Boc) strategy. The antagonist potency on NK-2 receptors in the hamster isolated trachea (HT) and the rabbit isolated pulmonary artery (RPA) bioassays increases with Xaa lipophilicity; I [Xaa = β-cyclohexylalanine, Asp(NHCH2Ph)] were the two most active antagonists (pA2 = 9.06 and 9.26 on HT, resp.). A significant linear correlation was found between pA2 values determined in HT and RPA bioassays and capacity factors measured in reversed phase HPLC. The comparison between the biol. activities of cyclic hexapeptides containing or not containing the aminomethylene moiety proved the crucial role of the pseudopeptide bond for determining high antagonist potency at the NK-2 receptor. In addition to this study using (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide, there are many other studies that have used (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Formula: C13H26N2O4) 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.Formula: C13H26N2O4

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

Patel, Bhavesh H.; Mason, Andrew M.; Patel, Hetal; Coombes, R. Charles; Ali, Simak; Barrett, Anthony G. M. published their research in Journal of Organic Chemistry on August 5 ,2011. The article was titled 《Conversion of α-Amino Acids into Bioactive o-Aminoalkyl Resorcylates and Related Dihydroxyisoindolinones》.Formula: C13H26N2O4 The article contains the following contents:

The synthesis of biol. active o-aminoalkyl resorcylates and related dihydroxyisoindolinones, e.g. I, from functionalized α-amino acids without the use of phenolic protection is described. The key aminoalkyl-diketo-dioxinone intermediates were prepared utilizing a crossed Claisen condensation reaction in the presence of diethylzinc. The aromatic unit was constructed via late stage cyclization and aromatization, and subsequent modification provided the novel resorcylates which showed activity against a selection of receptors and kinases, including 5-HT and CDK.(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Formula: C13H26N2O4) 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.Formula: C13H26N2O4

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