Author: Jessica.F

Dong, Xiao-Wu; Zhang, Jian-Kang; Xu, Lei; Che, Jin-Xin; Cheng, Gang; Hu, Xiao-Bei; Sheng, Li; Gao, An-Hui; Li, Jia; Liu, Tao; Hu, Yong-Zhou; Zhou, Yu-Bo published an article on February 15 ,2019. The article was titled 《Covalent docking modelling-based discovery of tripeptidyl epoxyketone proteasome inhibitors composed of aliphatic-heterocycles》, and you may find the article in European Journal of Medicinal Chemistry.Safety of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide The information in the text is summarized as follows:

The potential of specific proteasome inhibitors to act as anti-cancer agents has attracted intensive investigations. The proteasome can be covalently inhibited by epoxyketone derivatives via a two-step reaction. Several computational approaches have been developed to mimic the covalent binding event. Compound 1 (I) composed of a six-membered heterocyclic ring was designed by using covalent docking. With a possible different binding mode from the clin. compound Carfilzomib, it occupied the S5 pocket of 20S proteasome and showed favorable inhibitory activity. Subsequently optimization and evaluation were taken place. Among these compounds, 11h (II) demonstrated extraordinary in vitro inhibitory activity and selectivity, and good in vivo proteasome inhibitory activity, a favorable pharmacokinetic profile and xenograft tumor inhibition. The possible binding pattern of compound II against proteasome was further fully explored via calculations, providing a theor. basis for finding potent proteasome inhibitors. After reading the article, we found that the author used (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Safety 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. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole.Safety of (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

Garcia-Urricelqui, Ane; de Cozar, Abel; Mielgo, Antonia; Palomo, Claudio published an article on February 4 ,2021. The article was titled 《Probing α-Amino Aldehydes as Weakly Acidic Pronucleophiles: Direct Access to Quaternary α-Amino Aldehydes by an Enantioselective Michael Addition Catalyzed by Bronsted Bases》, and you may find the article in Chemistry – A European Journal.Recommanded Product: 87694-50-6 The information in the text is summarized as follows:

The chem. of α-amino aldehydes was expanded beyond their limits by documenting the first direct α-alkylation of α-branched α-amino aldehydes with nitroolefins. The reaction produced densely functionalized products bearing up to two, quaternary and tertiary, vicinal stereocenters with high diastereo- and enantioselectivity. DFT modeling lead to the proposal that intramol. hydrogen bonding between the NH group and the carbonyl oxygen atom in the starting α-amino aldehyde was key for reaction stereocontrol. 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. 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.Recommanded Product: 87694-50-6

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

In 2014,European Journal of Organic Chemistry included an article by Barroso, Raquel; Escribano, Maria; Cabal, Maria-Paz; Valdes, Carlos. Reference of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide. The article was titled 《Tosylhydrazide-Promoted Diastereoselective Intramolecular 1,3-Dipolar Cycloadditions: Synthesis of Tetrahydropyrrolo[3,4-c]pyrazoles》. The information in the text is summarized as follows:

A very straightforward diastereoselective synthesis of tetrahydropyrrolo[3,4-c]pyrazoles by intramol. 1,3-dipolar cycloaddition is described. The starting materials for the synthetic route are N-Boc-protected α-amino acids, which are first transformed into N-allyl-α-amino ketones through conventional methodologies. Then, a one-pot sequence that involves formation of a tosylhydrazone from the ketone, base-induced decomposition of the hydrazone, and intramol. 1,3-dipolar cycloaddition of the diazo compound generated, gives rise to the bicyclic systems with total diastereoselectivity and high preservation of the enantiomeric purity. However, the analogous process employing α-amino aldehydes lacks stereoselectivity. DFT computational modeling has been carried out to account for the different behavior of the two types of systems. 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: 87694-50-6Reference of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide) 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.“,” In primary and secondary amides, the presence of N–H dipoles allows amides to function as H-bond donors as well. Reference of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide

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

Peng, Tian-Yu; Xu, Zhe-Yuan; Zhang, Feng-Lian; Li, Bin; Xu, Wen-Ping; Fu, Yao; Wang, Yi-Feng published an article in Angewandte Chemie, International Edition. The title of the article was 《Dehydroxylative Alkylation of α-Hydroxy Carboxylic Acids Derivatives via a Spin-Center Shift》.Application In Synthesis of 2-Hydroxy-N-phenylacetamide The author mentioned the following in the article:

A strategically distinct dehydroxylative alkylation reaction of α-hydroxy carboxylic acid derivatives I (Ar1 = 4-NCC6H4, 4-EtO2CC6H4, 2-pyridyl, etc.) with alkenes is developed. The reaction starts with the attack of a 4-dimethylaminopyridine (DMAP)-boryl radical to the carbonyl oxygen atom, followed by a spin-center shift (SCS) to trigger the C-O bond scission. The resulting α-carbonyl radicals couple with a wide range of alkenes to furnish various alkylated products II (Ar1 = 4-NCC6H4, 4-EtO2CC6H4, 2-pyridyl, etc.; R = n-Bu, Ph, 3-MeC6H4, etc.) . This strategy allows for the efficient conversion of a wide array of α-hydroxy amides and esters derived from several biomass mols. and natural products to value-added compounds Exptl. and computational studies verified the reaction mechanism. In the experiment, the researchers used many compounds, for example, 2-Hydroxy-N-phenylacetamide(cas: 4746-61-6Application In Synthesis of 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.Application In Synthesis of 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

The author of 《Relative stabilities of glycolanilide and thioglycolanilide chelates》 were Apte, K. P.; Bhattacharya, A. K.. And the article was published in Journal of Inorganic and Nuclear Chemistry in 1973. Quality Control of 2-Hydroxy-N-phenylacetamide The author mentioned the following in the article:

Equilibrium constants were determined by pH titrations for complexation of H+ and M3+ (M = Al, Cr) with L (LH = glycolanilide, thioglycolanilide). In the part of experimental materials, we found many familiar compounds, such as 2-Hydroxy-N-phenylacetamide(cas: 4746-61-6Quality Control of 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.Quality Control of 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

In 2013,Selivanova, Svetlana V.; Stellfeld, Timo; Heinrich, Tobias K.; Muller, Adrienne; Kramer, Stefanie D.; Schubiger, P. August; Schibli, Roger; Ametamey, Simon M.; Vos, Bernhard; Meding, Jorg; Bauser, Marcus; Hutter, Joachim; Dinkelborg, Ludger M. published 《Design, Synthesis, and Initial Evaluation of a High Affinity Positron Emission Tomography Probe for Imaging Matrix Metalloproteinases 2 and 9》.Journal of Medicinal Chemistry published the findings.Reference of tert-Butyl N,N’-diisopropylcarbamimidate The information in the text is summarized as follows:

The activity of matrix metalloproteinases (MMPs) is elevated locally under many pathol. conditions. Gelatinases MMP2 and MMP9 are of particular interest because of their implication in angiogenesis, cancer cell proliferation and metastasis, and atherosclerotic plaque rupture. The aim of this study was to identify and develop a selective gelatinase inhibitor for imaging active MMP2/MMP9 in vivo. We synthesized a series of N-sulfonylamino acid derivatives with low to high nanomolar inhibitory potencies. (R)-2-(4-(4-Fluorobenzamido)phenylsulfonamido)-3-(1H-indol-3-yl)propanoic acid (7) exhibited the best in vitro binding properties: MMP2 IC50 = 1.8 nM, MMP9 IC50 = 7.2 nM. Radiolabeling of 7 with no carrier added 18F-radioisotope was accomplished starting from iodonium salts as precursors. The radiochem. yield strongly depended on the iodonium counteranion (ClO4- > Br- > TFA- > tosylate). 18F-7 was obtained in up to 20% radiochem. yield (decay corrected), high radiochem. purity, and >90 GBq/μmol specific radioactivity. The radiolabeled compound showed excellent stability in vitro and in mice in vivo. In the experiment, the researchers used many compounds, for example, tert-Butyl N,N’-diisopropylcarbamimidate(cas: 71432-55-8Reference of tert-Butyl N,N’-diisopropylcarbamimidate)

tert-Butyl N,N’-diisopropylcarbamimidate(cas: 71432-55-8) belongs to anime. To avoid the problem of multiple alkylation, methods have been devised for “blocking” substitution so that only one alkyl group is introduced. The Gabriel synthesis is one such method; it utilizes phthalimide, C6H4(CO)2NH, whose one acidic hydrogen atom has been removed upon the addition of a base such as KOH to form a salt.Reference of tert-Butyl N,N’-diisopropylcarbamimidate

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

In 2018,Lopez-Tapia, Francisco; Brotherton-Pleiss, Christine; Yue, Peibin; Murakami, Heide; Costa Araujo, Ana Carolina; Reis dos Santos, Bruna; Ichinotsubo, Erin; Rabkin, Anna; Shah, Raj; Lantz, Megan; Chen, Suzie; Tius, Marcus A.; Turkson, James published 《Linker variation and structure-activity relationship analysis of carboxylic acid-based small molecule STAT3 inhibitors》.ACS Medicinal Chemistry Letters published the findings.Application In Synthesis of tert-Butyl N,N’-diisopropylcarbamimidate The information in the text is summarized as follows:

The mol. determinants for the activities of the reported benzoic acid (SH4-54), salicylic acid (BP-1-102), and benzohydroxamic acid (SH5-07)-based STAT3 inhibitors were investigated to design optimized analogs. All three leads are based on an N-methylglycinamide scaffold, with its two amine groups condensed with three different functionalities. The three functionalities and the CH2 group of the glycinamide scaffold were sep. modified. The replacement of the pentafluorobenzene or cyclohexylbenzene, or replacing the benzene ring of the aromatic carboxylic or hydroxamic acid motif with heterocyclic components (containing nitrogen and oxygen elements) all decreased potency. Notably, the Ala-linker analogs, (I) (R1 = H and OH), and the Pro-based derivative (II) (X = CH2), all with (R)-configuration at the chiral center, had improved inhibitory activity and selectivity against STAT3 DNA-binding activity in vitro, with IC50 of 3.0 ± 0.9, 1.80 ± 0.94, and 2.4 ± 0.2 μM, resp. Compounds I and II and other analogs inhibited constitutive STAT3 phosphorylation and activation in human breast cancer and melanoma lines, and blocked tumor cell viability, growth, colony formation, and migration in vitro. Pro-based analog, II (X = O)(sodium salt), with a relatively polar tetrahydropyranyl (THP) ring, instead of the cyclohexyl, showed improved permeability. In general, the (R)-configuration Pro-based analogs showed the overall best profile, including physicochem. properties (e.g., microsomal metabolic stability, Caco-2 permeability), and in particular, II (X = CH2) showed improved tumor-cell specificity. The results came from multiple reactions, including the reaction of tert-Butyl N,N’-diisopropylcarbamimidate(cas: 71432-55-8Application In Synthesis of tert-Butyl N,N’-diisopropylcarbamimidate)

tert-Butyl N,N’-diisopropylcarbamimidate(cas: 71432-55-8) belongs to anime. In organic chemistry, amines are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (NH3), wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group (these may respectively be called alkylamines and arylamines; amines in which both types of substituent are attached to one nitrogen atom may be called alkylarylamines).Application In Synthesis of tert-Butyl N,N’-diisopropylcarbamimidate

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

In 2018,Yu, Jin-Sheng; Noda, Hidetoshi; Shibasaki, Masakatsu published 《Quaternary β2,2-amino acids: Catalytic asymmetric synthesis and incorporation into peptides by Fmoc-based solid-phase peptide synthesis》.Angewandte Chemie, International Edition published the findings.Recommanded Product: 71432-55-8 The information in the text is summarized as follows:

β-Amino acid incorporation has emerged as a promising approach to enhance the stability of parent peptides and to improve their biol. activity. Owing to the lack of reliable access to β2,2-amino acids in a setting suitable for peptide synthesis, most contemporary research efforts focus on the use of β3- and certain β2,3-amino acids. Herein, we report the catalytic asym. synthesis of β2,2-amino acids and their incorporation into peptides by Fmoc-based solid-phase peptide synthesis (Fmoc-SPPS). A quaternary carbon center was constructed by the palladium-catalyzed decarboxylative allylation of 4-substituted isoxazolidin-5-ones. The N-O bond in the products not only acts as a traceless protecting group for β-amino acids but also undergoes amide formation with α-ketoacids derived from Fmoc-protected α-amino acids, thus providing expeditious access to α-β2,2-dipeptides ready for Fmoc-SPPS. 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: 71432-55-8Recommanded Product: 71432-55-8) was used in this study.

tert-Butyl N,N’-diisopropylcarbamimidate(cas: 71432-55-8) belongs to anime. Amines characteristically form salts with acids; a hydrogen ion, H+, adds to the nitrogen. With the strong mineral acids (e.g., H2SO4, HNO3, and HCl), the reaction is vigorous. Salt formation is instantly reversed by strong bases such as NaOH. Neutral electrophiles (compounds attracted to regions of negative charge) also react with amines; alkyl halides (R′X) and analogous alkylating agents are important examples of electrophilic reagents.Recommanded Product: 71432-55-8

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

In 2018,Nowak, Monika; Fornal, Emilia; Kontek, Renata; Sroczynski, Dariusz; Jozwiak, Andrzej; Augustowska, Ewelina; Warpas, Anna; Adamczyk, Marta; Malinowski, Zbigniew published 《Synthesis of acylnaphthylamines and their applications in the formation of benzoquinazolines》.ARKIVOC (Gainesville, FL, United States) published the findings.SDS of cas: 78191-00-1 The information in the text is summarized as follows:

The synthesis of acyl N-Boc-1-naphthylamines I (R1 = Me, t-Bu) and N-Boc-2-naphthylamines II (R2 = Me, i-Pr) and their transformation into alkyl substituted benzoquinazolines III (R3 = Me, t-Bu; X = H, Br) and alkyl substituted benzoquinazolinones IV (R4 = Me, i-Pr), V (R5 = Me, t-Bu) through the reaction with formamide or potassium cyanate in the presence of ammonium acetate is described. Presented acyl derivatives were obtained from the reactions of the corresponding lithiated N-Boc naphthylamines with various acetylating agents like AcCl, Ac2O, AcOEt, PivCl, i-PrCOCl and also Weinreb amides. Biol. screening of the potential cytotoxicity on the HT29 cell line and lymphocytes were demonstrated for some benzoquinazoline derivatives After reading the article, we found that the author used N-Methoxy-N-methylacetamide(cas: 78191-00-1SDS of cas: 78191-00-1)

N-Methoxy-N-methylacetamide(cas: 78191-00-1) belongs to anime. In organic chemistry, amines are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (NH3), wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group (these may respectively be called alkylamines and arylamines; amines in which both types of substituent are attached to one nitrogen atom may be called alkylarylamines).SDS of cas: 78191-00-1

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

In 2018,Xiao, Peihong; Cao, Yanjun; Gui, Yingying; Gao, Lu; Song, Zhenlei published 《Me3Si-SiMe2[oCON(iPr)2-C6H4]: An Unsymmetrical Disilane Reagent for Regio- and Stereoselective Bis-Silylation of Alkynes》.Angewandte Chemie, International Edition published the findings.Application In Synthesis of N-Methoxy-N-methylacetamide The information in the text is summarized as follows:

The air-stable unsym. disilane Me3Si-SiMe2[o-CON(iPr)2C6H4] was developed for bis-silylation of alkynes. This reagent tolerates a range of functional groups, providing Z-vinyl disilanes in high yields. It is proposed that the phenyl-ring-tethered amide group directs oxidative addition of Pd0 into the Si-Si bond, which might facilitate formation of a six-membered Pd cycle, generating products with good to excellent regioselectivity. In the experimental materials used by the author, we found N-Methoxy-N-methylacetamide(cas: 78191-00-1Application In Synthesis of N-Methoxy-N-methylacetamide)

N-Methoxy-N-methylacetamide(cas: 78191-00-1) belongs to anime. Halogenation, in which one or more hydrogen atoms of an amine is replaced by a halogen atom, occurs with chlorine, bromine, and iodine, as well as with some other reagents, notably hypochlorous acid (HClO). With primary amines the reaction proceeds in two stages, producing N-chloro- and N,N-dichloro-amines, RNHCl and RNCl2, respectively. With tertiary amines, an alkyl group may be displaced by a halogen.Application In Synthesis of N-Methoxy-N-methylacetamide

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