Month: October 2022

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

In 2011,Aubry, Sylvain; Sasaki, Kaname; Eloy, Laure; Aubert, Genevieve; Retailleau, Pascal; Cresteil, Thierry; Crich, David published 《Exploring the potential of the β-thiolactones in bioorganic chemistry》.Organic & Biomolecular Chemistry published the findings.Product Details of 71432-55-8 The information in the text is summarized as follows:

A series of novel peptide-based β-thiolactones were synthesized and assayed for cytotoxicity against several human cancer cell lines, where they showed greater activity than the corresponding β-lactones and β-lactams. Several of the β-thiolactones prepared showed strong inhibitory activity in vitro against human cathepsins B and L. In the experiment, the researchers used tert-Butyl N,N’-diisopropylcarbamimidate(cas: 71432-55-8Product Details of 71432-55-8)

tert-Butyl N,N’-diisopropylcarbamimidate(cas: 71432-55-8) belongs to anime. Nitrous acid converts secondary amines (aliphatic or aromatic) to N-nitroso compounds (nitrosamines): R2NH + HNO2 → R2N―NO. Some nitrosamines are potent cancer-inducing substances, and their possible formation is a serious consideration when nitrites, which are salts of nitrous acid, are present in foods or pharmaceutical preparations. Tertiary amines give rise to nitrosamines more slowly; an alkyl group is eliminated as an aldehyde or ketone, along with nitrous oxide, N2O.Product Details of 71432-55-8

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

In 2016,Inai, Makoto; Ouchi, Hitoshi; Asahina, Aya; Asakawa, Tomohiro; Hamashima, Yoshitaka; Kan, Toshiyuki published 《Practical total syntheses of acromelic acids A and B》.Chemical & Pharmaceutical Bulletin published the findings.COA of Formula: C11H24N2O The information in the text is summarized as follows:

Practical total syntheses of acromelic acids A and B, which were scarce natural products isolated from toxic mushroom by Shirahama and Matsumoto, were accomplished in 13 (36% total yield) and 17 steps (6.9% total yield), resp., from 2,6-dichloropyridine. Beginning with regioselective transformation of sym. 2,6-dichloropyridine by either ortho-lithiation or bromination, nitroalkenes (I) (R1 = CO2Me, OMe; R2 = OMe, CO2t-Bu) were provided. Stereoselective construction of the vicinal stereocenters at the C-3, 4 positions of acromelic acids A and B was performed by a Ni-catalyzed asym. conjugate addition of α-ketoesters to the nitroalkenes. Construction of the pyrrolidine ring was accomplished in a single operation via a sequence consisting of reduction of the nitro group, intramol. condensation with the ketone, and reduction of the resulting ketimine. 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: 71432-55-8COA of Formula: C11H24N2O) was used in this study.

tert-Butyl N,N’-diisopropylcarbamimidate(cas: 71432-55-8) belongs to anime. Examples of direct uses of amines and their salts are as corrosion inhibitors in boilers and in lubricating oils (morpholine), as antioxidants for rubber and roofing asphalt (diarylamines), as stabilizers for cellulose nitrate explosives (diphenylamine), as protectants against damage from gamma radiation (diarylamines), as developers in photography (aromatic diamines), as flotation agents in mining, as anticling and waterproofing agents for textiles, as fabric softeners, in paper coating, and for solubilizing herbicides.COA of Formula: C11H24N2O

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

In 2019,Journal of the American Chemical Society included an article by Du, Kang; Thorarinsdottir, Agnes E.; Harris, T. David. Synthetic Route of C2H4BrNO. The article was titled 《Selective Binding and Quantitation of Calcium with a Cobalt-Based Magnetic Resonance Probe》. The information in the text is summarized as follows:

The authors report a cobalt-based paramagnetic chem. exchange saturation transfer (PARACEST) magnetic resonance (MR) probe that is able to selectively bind and quantitate the concentration of Ca2+ under physiol. conditions. The parent LCoII complex features an uncoordinated crown ether moiety in close proximity to the CoII center. Addition of Na+ or Ca2+ leads to binding of these metal ions within the crown ether. Single-crystal x-ray diffraction and solid-state magnetic measurements reveal the presence of a metal-specific coordination environment and magnetic anisotropy at Co, with the axial zero-field splitting parameter of the Na+ and Ca2+ complex differing by over 90%. Owing to these differences, solution-based measurements under physiol. conditions indicate reversible binding of Na+ and Ca2+ to give well-separated CEST peaks at 69 and 80 ppm, resp. Dissociation constants for different cation-bound complexes of LCo, as determined by 1H NMR spectroscopy, demonstrate high selectivity toward Ca2+. This finding, in conjunction with the large excess of Na+ in physiol. environments, minimizes interference from related cations, such as Mg2+ and K+. Finally, variable-[Ca2+] CEST spectra establish the ratio between the CEST peak intensities for the Ca2+- and Na+-bound probes (CEST80 ppm/CEST69 ppm) as a measure of [Ca2+], providing the first example of a ratiometric quantitation of Ca2+ concentration using PARACEST. Taken together, these results demonstrate the ability of transition metal PARACEST probes to afford a concentration-independent measure of [Ca2+], and provide a new approach for designing MR probes for cation sensing. The experimental part of the paper was very detailed, including the reaction process of 2-Bromoacetamide(cas: 683-57-8Synthetic Route of C2H4BrNO)

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.Synthetic Route of C2H4BrNO

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

In 2019,Chemistry – A European Journal included an article by Schwaerzer, Kuno; Bellan, Andreas; Zoeschg, Maximilian; Karaghiosoff, Konstantin; Knochel, Paul. Category: amides-buliding-blocks. The article was titled 《Magnesium Aldimines Prepared by Addition of Organomagnesium Halides to 2,4,6-Trichlorophenyl Isocyanide: Synthesis of 1,2-Dicarbonyl Derivatives》. The information in the text is summarized as follows:

The selective addition of organomagnesium reagents to 2,4,6-trichlorophenyl isocyanide leading to magnesiated aldimines I [R = n-Bu, Ph, Me2NC6H4, etc.] was reported. These aldimines reacted with Weinreb amides, ketones or carbonates to provide the corresponding carbonyl derivatives after acidic cleavage. This allowed for an efficient synthesis of 1,2-dicarbonyl compounds II [R1 = c-hexyl, Ph, 4-MeOC6H4, etc.] and α-hydroxy ketones III [R2R3 = (CH2)5, R2 = R3 = Ph, R2 = c-Pr, R3 = 4-FC6H4].N-Methoxy-N-methylacetamide(cas: 78191-00-1Category: amides-buliding-blocks) was used in this study.

N-Methoxy-N-methylacetamide(cas: 78191-00-1) belongs to anime. Reduction of nitro compounds, RNO2, by hydrogen or other reducing agents produces primary amines cleanly (i.e., without a mixture of products), but the method is mostly used for aromatic amines because of the limited availability of aliphatic nitro compounds. Reduction of nitriles and oximes (R2C=NOH) also yields primary amines.Category: amides-buliding-blocks

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

The author of 《Synthesis and identification of heteroaromatic N-benzyl sulfonamides as potential anticancer agents》 were Hopkins, Megan D.; Abebe, Felagot A.; Scott, Kristina A.; Ozmer, Garett L.; Sheir, Alec A.; Schroeder, Lucas J.; Sheaff, Robert J.; Lamar, Angus A.. And the article was published in Organic & Biomolecular Chemistry in 2019. Related Products of 70-55-3 The author mentioned the following in the article:

A new approach for regioselective incorporation of a sulfonamide unit to heteroarene scaffolds has been developed and is reported within. As a result, a variety of primary benzylic N-alkylsulfonamides have been prepared via a two-step (one pot) formation from the in situ reduction of an intermediate N-sulfonyl imine under mild, practical conditions. The compounds have been screened against a variety of cell lines for cytotoxicity effects using a Cell Titer Blue assay. The cell viability investigation identifies a subset of N-benzylic sulfonamides derived from the indole scaffold to be targeted for further development into novel mols. with potential therapeutic value. The most cytotoxic of the compounds prepared, I (R1 = Me, R2,R3 = H; R4 = 4-ClC6H4), exhibited higher potency than other well-known anticancer agents Indisulam and ABT-751. The results came from multiple reactions, including the reaction of 4-Methylbenzenesulfonamide(cas: 70-55-3Related Products of 70-55-3)

4-Methylbenzenesulfonamide(cas: 70-55-3) belongs to anime. Hydrogen peroxide (H2O2) and peroxy acids generally add an oxygen atom to the nitrogen of amines. With primary amines, this step is normally followed by further oxidation, leading to nitroso compounds, RNO, or nitro compounds, RNO2. Secondary amines are converted to hydroxylamines, R2NOH, and tertiary amines to amine oxides, R3NO.Related Products of 70-55-3

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

《Synthesis and structures of amido-functionalized N-heterocyclic nickel(II) carbene complexes》 was published in Journal of Organometallic Chemistry in 2020. These research results belong to Lu, Sheng-Zhi; Yang, Hsueh-Hui; Chang, Wei-Ju; Hsueh, Hsin-Hsueh; Lin, Yong-Chieh; Liu, Fu-Chen; Lin, Ivan J. B.; Lee, Gene-Hsiang. Product Details of 683-57-8 The article mentions the following:

A series of bis-bidentate nickel(II) complexes [Ni(R-bimy-CH2CONH)2] (bimyH = benzimidazole; R = Me (3), Et (4), Ph (5)) bearing amido-functionalized N-heterocyclic carbene ligands, and pincer-type nickel(II) complexes [Ni(Py-bimy-CH2CONH)X] (X = Cl (6), Br (7)) bearing an amido- and pyridyl-functionalized N-heterocyclic carbene ligand were prepared These complexes were characterized by NMR (1D and 2D) and single-crystal x-ray diffraction. Complexes 3-5 possess cis configuration, and the carbene ligands bound to the nickel atom through C2 carbon and NH nitrogen in a bis-bidentate coordination mode. In complexes 6 and 7, the pyridyl substituent was also N-bound to the nickel metal center resulting in a pincer-type coordination mode. As observed from the proton NMR spectra, the six-membered chelate rings in complexes 3-5 rendered the protons of the methylene moieties diastereotopic, and the cis configuration made the free rotation of the Et substituent in 4 and the Ph substituent in 5 hampered by the adjacent substituent. The catalytic activity of these nickel complexes in Kumada cross-coupling of phenylmagnesium bromide with aryl chlorides was also investigated. The results indicated that pincer-type complexes 6 and 7 displayed excellent to moderate catalytic activity depending on the aryl chloride used.2-Bromoacetamide(cas: 683-57-8Product Details of 683-57-8) was used in this study.

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.Product Details of 683-57-8

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