Month: October 2022

Goetz, D. H.; Choe, Y.; Hansell, E.; Chen, Y. T.; McDowell, M.; Jonsson, C. B.; Roush, B. C.; McKerrow, J.; Craik, C. S. published an article in Biochemistry. The title of the article was 《Substrate Specificity Profiling and Identification of a New Class of Inhibitor for the Major Protease of the SARS Coronavirus》.Application In Synthesis of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide The author mentioned the following in the article:

Severe acute respiratory syndrome (SARS) is an emerging infectious disease associated with a high rate of mortality. The SARS-associated coronavirus (SARS-CoV) has been identified as the etiol. agent of the disease. Although public health procedures have been effective in combating the spread of SARS, concern remains about the possibility of a recurrence. Various approaches are being pursued for the development of efficacious therapeutics. One promising approach is to develop small mol. inhibitors of the essential major polyprotein processing protease 3Clpro. Here we report a complete description of the tetrapeptide substrate specificity of 3Clpro using fully degenerate peptide libraries consisting of all 160 000 possible naturally occurring tetrapeptides. The substrate specificity data show the expected P1-Gln P2-Leu specificity and elucidate a novel preference for P1-His containing substrates equal to the expected preference for P1-Gln. These data were then used to develop optimal substrates for a high-throughput screen of a 2000 compound small-mol. inhibitor library consisting of known cysteine protease inhibitor scaffolds. We also report the 1.8 Å X-ray crystal structure of 3Clpro bound to an irreversible inhibitor. This inhibitor, an α,β-epoxyketone, inhibits 3Clpro with a k3/Ki of 0.002 μM-1 s-1 in a mode consistent with the substrate specificity data. Finally, we report the successful rational improvement of this scaffold with second generation inhibitors. These data provide the foundation for a rational small-mol. inhibitor design effort based upon the inhibitor scaffold identified, the crystal structure of the complex, and a more complete understanding of P1-P4 substrate specificity. After reading the article, we found that the author used (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. 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. Application In Synthesis of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide

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

Hu, Xiafei; Chen, Xiangxiang; Li, Bo; He, Gang; Chen, Gong published an article on February 5 ,2021. The article was titled 《Construction of peptide macrocycles via radical-mediated intramolecular C-H alkylations》, and you may find the article in Organic Letters.Quality Control of H-Lys(Boc)-OH The information in the text is summarized as follows:

Enzyme-catalyzed radical-mediated C-H functionalization reactions allow nature to create natural products of unusual three-dimensional structures from simple linear peptide precursors. In comparison, chemist’s ability to harness radical C-H functionalization reactions for synthesis of complex peptides remains limited. In this work, new methods have been developed to construct peptide macrocycles via radical-mediated intramol. C-H alkylation reactions under photoredox catalysis. Linear peptide precursors equipped with a C-terminal N-(acyloxy)phthalimide ester can cyclize with the α C-H bond of N-terminal glycine or aryl C-H bond of N-heteroarene capping units in high yield and selectivity under mild conditions. The strategy uses the C-H cyclization step to incorporate lysine, homolysine, and various heteroarene-derived amino acid linchpins into peptide macrocycles, enabling convergent and flexible synthesis of complex peptide macrocycles from simple building blocks. The results came from multiple reactions, including the reaction of H-Lys(Boc)-OH(cas: 2418-95-3Quality Control of H-Lys(Boc)-OH)

H-Lys(Boc)-OH(cas: 2418-95-3) belongs to amino acids. In addition to subunits of proteins, amino acids have many other functions as well, including osmoregulation (proline), neurotransmitters (gamma-aminobutyric acid), metabolic intermediates (ornithine and citrulline), and inhibitors (dehydroproline).Quality Control of H-Lys(Boc)-OH

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

The author of 《Tuning gel state properties of supramolecular gels by functional group modification》 were Ghosh, Dipankar; Mulvee, Matthew T.; Damodaran, Krishna K.. And the article was published in Molecules in 2019. Recommanded Product: 64479-78-3 The author mentioned the following in the article:

The factors affecting the self-assembly process in low mol. weight gelators (LMWGs) were investigated by tuning the gelation properties of a well-known gelator N-(4-pyridyl)isonicotinamide (4PINA). The N-H···N interactions responsible for gel formation in 4PINA were disrupted by altering the functional groups of 4PINA, which was achieved by modifying pyridyl moieties of the gelator to pyridyl N-oxides. We synthesized two mono-N-oxides (INO and PNO) and a di-N-oxide (diNO) and the gelation studies revealed selective gelation of diNO in water, but the two mono-N-oxides formed crystals. The mech. strength and thermal stabilities of the gelators were evaluated by rheol. and transition temperature (Tgel) experiments, resp., and the anal. of the gel strength indicated that diNO formed weak gels compared to 4PINA. The SEM image of diNO xerogels showed fibrous microcrystalline networks compared to the efficient fibrous morphol. in 4PINA. Single-crystal X-ray anal. of diNO gelator revealed that a hydrogen-bonded dimer interacts with adjacent dimers via C-H···O interactions. The non-gelator with similar dimers interacted via C-H···N interaction, which indicates the importance of specific non-bonding interactions in the formation of the gel network. The solvated forms of mono-N-oxides support the fact that these compounds prefer crystalline state rather than gelation due to the increased hydrophilic interactions. The reduced gelation ability (min. gel concentration (MGC)) and thermal strength of diNO may be attributed to the weak intermol. C-H···O interaction compared to the strong and unidirectional N-H···N interactions in 4PINA. In the experiment, the researchers used many compounds, for example, N-(Pyridin-4-yl)isonicotinamide(cas: 64479-78-3Recommanded Product: 64479-78-3)

N-(Pyridin-4-yl)isonicotinamide(cas: 64479-78-3) 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. Recommanded Product: 64479-78-3

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

In 2019,Chemical Science included an article by Zhang, Ziyan; Yadagiri, Dongari; Gevorgyan, Vladimir. Synthetic Route of C7H9NO2S. The article was titled 《Light-induced metal-free transformations of unactivated pyridotriazoles》. The information in the text is summarized as follows:

A highly efficient and practical method for incorporation of the arylmethylpyridyl moiety into diverse mols. were developed. This method features the transition metal-free light-induced room temperature transformation of pyridotriazoles into pyridyl carbenes, which were capable of smooth arylation, X-H insertion and cyclopropanation reactions. The synthetic usefulness of the developed method was illustrated in a facile synthesis of biol. active mols. In the part of experimental materials, we found many familiar compounds, such as 4-Methylbenzenesulfonamide(cas: 70-55-3Synthetic Route of C7H9NO2S)

4-Methylbenzenesulfonamide(cas: 70-55-3) belongs to anime. Amine, any member of a family of nitrogen-containing organic compounds that is derived, either in principle or in practice, from ammonia (NH3). Naturally occurring amines include the alkaloids, which are present in certain plants; the catecholamine neurotransmitters (i.e., dopamine, epinephrine, and norepinephrine); and a local chemical mediator, histamine, that occurs in most animal tissues.Synthetic Route of C7H9NO2S

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

In 2019,Heterocycles included an article by Tanimoto, Iku; Kawai, Kentaro; Sato, Akane; Yoshino, Tatsuhiko; Matsunaga, Shigeki. Recommanded Product: N-Methoxy-N-methylacetamide. The article was titled 《One-step synthesis of 4H-3,1-benzoxazin-4-ones from Weinreb amides and 1,4,2-dioxazol-5-ones via cobalt-catalyzed C-H bond activation》. The information in the text is summarized as follows:

A one-step synthesis of 4H-3,1-benzoxazin-4-ones e.g., 2-phenyl-4H-benzo[d][1,3]oxazin-4-one from readily available Weinreb amides I (R = t-Bu, Ph, thiophen-2-yl, etc.) and 1,4,2-dioxazol-5-ones e.g., N-methoxy-N-methylbenzamide under Cp*Co(III) catalysis is described. The reactions proceeded in moderate to good yields with high functional group compatibility. After reading the article, we found that the author used N-Methoxy-N-methylacetamide(cas: 78191-00-1Recommanded Product: N-Methoxy-N-methylacetamide)

N-Methoxy-N-methylacetamide(cas: 78191-00-1) belongs to anime. Aniline, ethanolamines, and several other amines are major industrial commodities used in making rubber, dyes, pharmaceuticals, and synthetic resins and fibres and for a host of other applications. Most of the numerous methods for the preparation of amines may be broadly divided into two groups: (1) chemical reduction (replacement of oxygen with hydrogen atoms in the molecule) of members of several other classes of organic nitrogen compounds and (2) reactions of ammonia or amines with organic compounds.Recommanded Product: N-Methoxy-N-methylacetamide

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

The author of 《Highly fluorinated metal complexes as dual 19F and PARACEST imaging agents》 were Yu, Meng; Bouley, Bailey S.; Xie, Da; Que, Emily L.. And the article was published in Dalton Transactions in 2019. Category: amides-buliding-blocks The author mentioned the following in the article:

We reported a set of water-soluble transition metal complexes that can serve as both 19F and PARACEST magnetic resonance imaging agents. The high number of equivalent fluorine atoms and the paramagnetic effect of metals offer these complexes high 19F sensitivity as demonstrated by in vitro19F MRI experiments The complexes contain carboxamide groups appended onto a cyclen macrocycle, which provide 1H CEST peaks well differentiated from bulk water. The Co(II) agent displays two CEST peaks that can be utilized for ratiometric pH determination and the concept of combining 19F MR and PARACEST as complementary imaging techniques was demonstrated with the Fe(II) complex.2-Bromoacetamide(cas: 683-57-8Category: amides-buliding-blocks) 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.Category: amides-buliding-blocks

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

《Copper-catalyzed carbonylative synthesis of β-homoprolines from N-fluoro-sulfonamides》 was published in Organic Letters in 2020. These research results belong to Zhang, Youcan; Yin, Zhiping; Wu, Xiao-Feng. Recommanded Product: 70-55-3 The article mentions the following:

A new methodol. for the carbonylative transformation of N-fluoro-sulfonamides into N-sulfonyl-β-homoproline esters has been described. In the presence of a catalytic amount of Cu(OTf)2, a range of β-homoproline derivatives were prepared in moderate to good yield. The reaction proceeds via the intramol. cyclization and intermol. carbonylation of a free carbon radical. Notably, this procedure offers the possibility to build potential functionalized bioactive mols. The experimental process involved the reaction of 4-Methylbenzenesulfonamide(cas: 70-55-3Recommanded Product: 70-55-3)

4-Methylbenzenesulfonamide(cas: 70-55-3) 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.Recommanded Product: 70-55-3

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

《Direct inhibition of Keap1-Nrf2 Protein-Protein interaction as a potential therapeutic strategy for Alzheimer’s disease》 was written by Sun, Yi; Huang, Jiaxuan; Chen, Yufei; Shang, Hao; Zhang, Wannian; Yu, Jianqiang; He, Ling; Xing, Chengguo; Zhuang, Chunlin. Related Products of 683-57-8 And the article was included in Bioorganic Chemistry in 2020. The article conveys some information:

The Kelch-like ECH-associated protein 1 (Keap1)-nuclear factor erythroid 2-related factor 2 (Nrf2) pathway works as the key regulator against oxidative stress damage in many cells and organs. It has been a widely proposed therapeutic target for neurodegenerative diseases, including Alzheimer’s disease (AD). This study aimed at determining the neuroprotective activity of 9 (NXPZ-2), a small-mol. compound that directly inhibits the Keap1-Nrf2 protein-protein interaction, in an amyloid beta 1-42 (Aβ1-42) oligomer intracerebroventricularly (i.c.v.) injected mouse model. Behavioral tests showed that NXPZ-2 treatment dose-relatedly ameliorated learning and memory dysfunction in Aβ1-42-treated mice. HE and Nissl staining showed that NXPZ-2 improved brain tissue pathol. changes in AD mice by increasing neuron quantity and function. Western blot anal. of the hippocampus and cortex showed up-regulated Nrf2 in whole cell lysate, with increased nuclear translocation to increase Nrf2-targeted antioxidant enzymes (HO-1, NQO-1) and decreased p-Tau in NXPZ-2-treated mice. ELISA results showed that NXPZ-2 treatment increased serum Nrf2 and significantly decreased serum Aβ1-42 levels in AD mice. Furthermore, hippocampal and cortical superoxide dismutase (SOD) and glutathione (GSH) levels increased, while malondialdehyde (MDA) levels decreased. No obvious toxicity was observed in primary cultured mouse cortical neurons and organs with NXPZ-2 treatment. No ameliorative effect was observed of NXPZ-2 in Nrf2 knockout AD mice. Collectively, our findings demonstrated that NXPZ-2 could be a promising therapeutic agent against AD, and provided the first set of exptl. evidence, in a mouse model, to support Keap1-Nrf2 interaction as a validated target for the Nrf2 reactivation in AD.2-Bromoacetamide(cas: 683-57-8Related Products 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.Related Products of 683-57-8

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

In 2022,Pitcher, Noel P.; Harjani, Jitendra R.; Zhao, Yichao; Jin, Jianwen; Knight, Daniel R.; Li, Lucy; Putsathit, Papanin; Riley, Thomas V.; Carter, Glen P.; Baell, Jonathan B. published an article in ACS Omega. The title of the article was 《Development of 1,2,4-Oxadiazole Antimicrobial Agents to Treat Enteric Pathogens within the Gastrointestinal Tract》.Formula: C11H24N2O The author mentioned the following in the article:

Colonization of the gastrointestinal (GI) tract with pathogenic bacteria is an important risk factor for the development of certain potentially severe and life-threatening healthcare-associated infections, yet efforts to develop effective decolonization agents have been largely unsuccessful thus far. Herein, we report modification of the 1,2,4-oxadiazole class of antimicrobial compounds with poorly permeable functional groups in order to target bacterial pathogens within the GI tract. We have identified that the quaternary ammonium functionality of analog 26a (I) results in complete impermeability in Caco-2 cell monolayers while retaining activity against GI pathogens Clostridioides difficile and multidrug-resistant (MDR) Enterococcus faecium. Low compound recovery levels after oral administration in rats were observed, which suggests that the analogs may be susceptible to degradation or metabolism within the gut, highlighting a key area for optimization in future efforts. This study demonstrates that modified analogs of the 1,2,4-oxadiazole class may be potential leads for further development of colon-targeted antimicrobial agents. 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: 71432-55-8Formula: C11H24N2O) was used in this study.

tert-Butyl N,N’-diisopropylcarbamimidate(cas: 71432-55-8) belongs to anime. Milder oxidation, using reagents such as NaOCl, can remove four hydrogen atoms from primary amines of the type RCH2NH2 to form nitriles (R―C≡N), and oxidation with reagents such as MnO2 can remove two hydrogen atoms from secondary amines (R2CH―NHR′) to form imines (R2C=NR′). Tertiary amines can be oxidized to enamines (R2C=CHNR2) by a variety of reagents.Formula: C11H24N2O

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

Recommanded Product: 70-55-3In 2022 ,《Visible Light-Mediated Late-stage Sulfonylation of Anilines with Sulfonamides》 was published in Organic Letters. The article was written by Xu, Xiao-Hong; Zhen, Jing-Song; Du, Xian; Yuan, Han; Li, Yi-Hui; Chu, Man-Hei; Luo, Yong. The article contains the following contents:

A visible light-mediated late-stage sulfonylation of anilines with sulfonamides under simple reaction conditions is presented. Various primary or secondary sulfonamides including several pharmaceuticals were incorporated successfully via N-S bond activation and C-H bond sulfonylation. The synthetic utility of this strategy is highlighted by the construction of complex anilines bearing diverse bioactive groups. In the experiment, the researchers used many compounds, for example, 4-Methylbenzenesulfonamide(cas: 70-55-3Recommanded Product: 70-55-3)

4-Methylbenzenesulfonamide(cas: 70-55-3) 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.Recommanded Product: 70-55-3

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