Month: October 2022

Formula: C7H9NO2SIn 2022 ,《Solvent-Triggered Long-Range Proton Transport in 7-Hydroxyquinoline Using a Sulfonamide Transporter Group》 was published in Journal of Organic Chemistry. The article was written by Nakashima, Kosuke; Georgiev, Anton; Yordanov, Dancho; Matsushima, Yasuyuki; Hirashima, Shin-ichi; Miura, Tsuyoshi; Antonov, Liudmil. The article contains the following contents:

The ability of long-range proton transport by substitution of 7-hydroxyquinoline at the eighth position with sulfonamide and sulfonylhydrazone rotor units to act as a crane-arm has been studied. Different proton transport pathways triggered by different stimuli have been established depending on the structure of the crane-arms. Solvent-driven proton switching from OH to the quinoline nitrogen (Nquin) site, facilitated by a sulfonamide transporter group in polar protic and aprotic solvents, has been confirmed by optical (absorption and fluorescence) and NMR spectroscopies as well as by single-crystal X-ray structure anal. Photoinduced long-range proton transport to the Nquin site upon 340 nm UV light irradiation has been estimated in sulfonylhydrazone, which is not sensitive to solvent-driven switching. Both compounds have exhibited acid-triggered switching by trifluoroacetic acid due to the formation of a stable six-membered intramol. hydrogen bonding interaction between the protonated Nquin and crane-arm. The structures of acid-switched form were confirmed by NMR spectroscopy and single-crystal X-ray structure anal. The behavior of the compounds suggests a big step forward in the advanced proton pump-switching architecture because they cover three distinct driving forces in the switching process: solvent, light, and acid. The experimental part of the paper was very detailed, including the reaction process of 4-Methylbenzenesulfonamide(cas: 70-55-3Formula: C7H9NO2S)

4-Methylbenzenesulfonamide(cas: 70-55-3) belongs to anime. Amines have a free lone pair with which they can coordinate to metal centers. Amine–metal bonds are weaker because amines are incapable of backbonding, but they are still important for sensing applications.While stronger than hydrogen bonds, amine–metal bonds are still weaker than both covalent and ionic bonds.Formula: C7H9NO2S

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

《An easy and convenient synthesis of Weinreb amides and hydroxamates》 was written by de Luca, Lidia; Giacomelli, Giampaolo; Taddei, Maurizio. Synthetic Route of C13H26N2O4 And the article was included in Journal of Organic Chemistry on April 6 ,2001. The article conveys some information:

A simple and convenient one-flask method for the preparation of Weinreb amides, hydroxamates, and hydroxamic acids on a large scale used mild reaction conditions and inexpensive reagents; the methodol. is a useful addition to parallel syntheses. Thus, reacting PhCO2H with MeNHOMe in THF containing 2-chloro-4,6-dimethoxy-1,3,5-triazine [CMDT], 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride [DMTMM], or cyanuric chloride and N-methylmorpholine [NMM] gave the amide PhCONMeOMe in high yields. The results came from multiple reactions, including the reaction of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Synthetic Route of C13H26N2O4)

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

《Copper(I)-mediated denitrogenative macrocyclization for the synthesis of cyclic α3β-tetrapeptide analogs》 was published in Chemistry – An Asian Journal in 2017. These research results belong to Chen, Chun-Chi; Wang, Sheng-Fu; Su, Yung-Yu; Lin, Yuya A.; Lin, Po-Chiao. Related Products of 87694-50-6 The article mentions the following:

A copper(I)-mediated denitrogenative reaction has been successfully developed for the preparation of cyclic tetrapeptides. The key reactive intermediate, ketenimine, triggers intramol. cyclization through attack of the terminal amine group to generate an internal β-amino acid with an amidine linkage. The chem. developed herein provides a new synthetic route for the preparation of cyclic α3β-tetrapeptide analogs that contain important biol. properties and results in rich structural information being obtained for conformational studies. With the success of this copper(I)-catalyzed macrocyclization, two histone deacetylase inhibitor analogs consisting of the cyclic α3β-tetrapeptide framework have been successfully synthesized. 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: 87694-50-6Related Products of 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.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

Estel, L.; Linard, F.; Marsais, F.; Godard, A.; Queguiner, G. published an article on February 28 ,1989. The article was titled 《Synthesis of ortho-substituted aminopyridines. Metalation of pivaloylamino derivatives》, and you may find the article in Journal of Heterocyclic Chemistry.Electric Literature of C10H14N2O The information in the text is summarized as follows:

The three isomeric (pivaloylamino)pyridines were lithiated and treated with various electrophiles to afford ortho-substituted pivaloylaminopyridines in good yields. Secondary pyridine alcs. were oxidized to the corresponding aminopyridyl ketones. Pyridopyrimidines, benzonaphthyridines, as well as an analog of the natural antitumor alkaloid ellipticine, were synthesized by this method. The experimental process involved the reaction of 2,2-Dimehtyl-N-pyridin-3-yl-propionamide(cas: 70298-88-3Electric Literature of C10H14N2O)

2,2-Dimehtyl-N-pyridin-3-yl-propionamide(cas: 70298-88-3) belongs to anime. The reaction of alkyl halides, R―X, where X is a halogen, or analogous reagents with ammonia (or amines) is useful with certain compounds. Not all alkyl halides are effective reagents; the reaction is sluggish with secondary alkyl groups and fails with tertiary ones. Its usefulness is largely confined to primary alkyl halides (those having two hydrogen atoms on the reacting site).Electric Literature of C10H14N2O

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

Lee, Min Jae; Bhattarai, Deepak; Jang, Hyeryung; Baek, Ahreum; Yeo, In Jun; Lee, Seongsoo; Miller, Zachary; Lee, Sukyeong; Hong, Jin Tae; Kim, Dong-Eun; Lee, Wooin; Kim, Kyung Bo published their research in Journal of Medicinal Chemistry on August 12 ,2021. The article was titled 《Macrocyclic Immunoproteasome Inhibitors as a Potential Therapy for Alzheimer’s Disease》.Category: amides-buliding-blocks The article contains the following contents:

Previously, we reported that immunoproteasome (iP)-targeting linear peptide epoxyketones improve cognitive function in mouse models of Alzheimer’s disease (AD) in a manner independent of amyloid β. However, these compounds’ clin. prospect for AD is limited due to potential issues, such as poor brain penetration and metabolic instability. Here, we report the development of iP-selective macrocyclic peptide epoxyketones prepared by a ring-closing metathesis reaction between two terminal alkenes attached at the P2 and P3/P4 positions of linear counterparts. We show that a lead macrocyclic compound DB-60 (20) effectively inhibits the catalytic activity of iP in ABCB1-overexpressing cells (IC50: 105 nM) and has metabolic stability superior to its linear counterpart. DB-60 (20) also lowered the serum levels of IL-1α and ameliorated cognitive deficits in Tg2576 mice. The results collectively suggest that macrocyclic peptide epoxyketones have improved CNS drug properties than their linear counterparts and offer promising potential as an AD drug candidate. In the experimental materials used by the author, we found (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Category: amides-buliding-blocks)

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

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,Starr, Jeremy; Brown, Matthew F.; Aschenbrenner, Lisa; Caspers, Nicole; Che, Ye; Gerstenberger, Brian S.; Huband, Michael; Knafels, John D.; Lemmon, M. Megan; Li, Chao; McCurdy, Sandra P.; McElroy, Eric; Rauckhorst, Mark R.; Tomaras, Andrew P.; Young, Jennifer A.; Zaniewski, Richard P.; Shanmugasundaram, Veerabahu; Han, Seungil published 《Siderophore receptor-mediated uptake of lactivicin analogs in Gram-negative bacteria》.Journal of Medicinal Chemistry published the findings.Reference of tert-Butyl N,N’-diisopropylcarbamimidate The information in the text is summarized as follows:

Multidrug-resistant Gram-neg. pathogens are an emerging threat to human health, and addressing this challenge will require development of new antibacterial agents. This can be achieved through an improved mol. understanding of drug-target interactions combined with enhanced delivery of these agents to the site of action. Here, the authors describe the first application of siderophore receptor-mediated drug uptake of lactivicin analogs as a strategy that enables the development of novel antibacterial agents against clin. relevant Gram-neg. bacteria. They report the first crystal structures of several sideromimic conjugated compounds bound to penicillin binding proteins PBP3 and PBP1a from Pseudomonas aeruginosa and characterize the reactivity of lactivicin and β-lactam core structures. Results from drug sensitivity studies with β-lactamase enzymes are presented, as well as a structure-based hypothesis to reduce susceptibility to this enzyme class. Finally, mechanistic studies demonstrating that sideromimic modification alters the drug uptake process are discussed. 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. Reaction with nitrous acid (HNO2), which functions as an acylating agent that is a source of the nitrosyl group (―NO), converts aliphatic primary amines to nitrogen and mixtures of alkenes and alcohols corresponding to the alkyl group in a complex process. This reaction has been used for analytical determination of primary amino groups in a procedure known as the Van Slyke method.Reference of tert-Butyl N,N’-diisopropylcarbamimidate

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

In 2015,Ikubo, Masaya; Inoue, Asuka; Nakamura, Sho; Jung, Sejin; Sayama, Misa; Otani, Yuko; Uwamizu, Akiharu; Suzuki, Keisuke; Kishi, Takayuki; Shuto, Akira; Ishiguro, Jun; Okudaira, Michiyo; Kano, Kuniyuki; Makide, Kumiko; Aoki, Junken; Ohwada, Tomohiko published 《Structure-Activity Relationships of Lysophosphatidylserine Analogs as Agonists of G-Protein-Coupled Receptors GPR34, P2Y10, and GPR174》.Journal of Medicinal Chemistry published the findings.HPLC of Formula: 71432-55-8 The information in the text is summarized as follows:

Lysophosphatidylserine (LysoPS) is an endogenous lipid mediator generated by hydrolysis of membrane phospholipid phosphatidylserine. Recent ligand screening of orphan G-protein-coupled receptors (GPCRs) identified two LysoPS-specific human GPCRs, namely, P2Y10 (LPS2) and GPR174 (LPS3), which, together with previously reported GPR34 (LPS1), comprise a LysoPS receptor family. Herein, the authors examined the structure-activity relationships of a series of synthetic LysoPS analogs toward these recently deorphanized LysoPS receptors, based on the idea that LysoPS can be regarded as consisting of distinct modules (fatty acid, glycerol, and L-serine) connected by phosphodiester and ester linkages. Starting from the endogenous ligand (1-oleoyl-LysoPS), the authors optimized the structure of each module and the ester linkage. Accordingly, the authors identified some structural requirements of each module for potency and for receptor subtype selectivity. Further assembly of individually structure-optimized modules yielded a series of potent and LysoPS receptor subtype-selective agonists, particularly for P2Y10 and GPR174. 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: 71432-55-8HPLC of Formula: 71432-55-8) 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.HPLC of Formula: 71432-55-8

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

In 2017,Li, Wenjing; Yin, Changzhen; Yang, Xiao; Liu, Hailong; Zheng, Xueli; Yuan, Maolin; Li, Ruixiang; Fu, Haiyan; Chen, Hua published 《Cu(II)-Mediated keto C(sp3)-H bond α-acyloxylation of N,N-dialkylamides with aromatic carboxylic acids》.Organic & Biomolecular Chemistry published the findings.Safety of N-Methoxy-N-methylacetamide The information in the text is summarized as follows:

The selective oxidative coupling of aromatic carboxylic acids with the C(sp3)-H bond adjacent to the keto group of alkylamides was developed by employing a low cost copper source. This provides an efficient approach for synthesis of O-benzoylglycolamides. The protocol displayed good functional group tolerance. A broad range of benzoic acids directly coupled with alkylamides to afford a variety of O-benzoylglycolamides in moderate to good yields. In addition, a reasonable radical mechanism was proposed based on EPR experiments In the part of experimental materials, we found many familiar compounds, such as N-Methoxy-N-methylacetamide(cas: 78191-00-1Safety of N-Methoxy-N-methylacetamide)

N-Methoxy-N-methylacetamide(cas: 78191-00-1) belongs to anime. Amines have a free lone pair with which they can coordinate to metal centers. Amine–metal bonds are weaker because amines are incapable of backbonding, but they are still important for sensing applications.While stronger than hydrogen bonds, amine–metal bonds are still weaker than both covalent and ionic bonds.Safety of N-Methoxy-N-methylacetamide

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

In 2018,Xin, Bo-Tao; van Tol, Bianca D. M.; Ovaa, Huib; Geurink, Paul P. published 《Native chemical ligation at methionine bioisostere norleucine allows for N-terminal chemical protein ligation》.Organic & Biomolecular Chemistry published the findings.Computed Properties of C11H24N2O The information in the text is summarized as follows:

The development of γ-thionorleucine (ThioNle) as a handle for native chem. ligation-desulfurization is reported here. ThioNle is a new addition to the expanding thiolated amino acid toolbox and serves as a methionine substitute in NCL with the advantage that it lacks the undesirable oxidation-prone thioether moiety. Its usefulness for N-terminal ubiquitination is demonstrated by efficient preparation of fully synthetic linear diubiquitin with preserved protein folding compared to the expressed material. Interestingly, gel-based deubiquitinating assays revealed that the methionine to norleucine substitution did affect diubiquitin cleavage, which may indicate a more profound role for methionine in the interaction between ubiquitin and the deubiquitinating enzymes than has been known so far. In the experiment, the researchers used tert-Butyl N,N’-diisopropylcarbamimidate(cas: 71432-55-8Computed Properties of C11H24N2O)

tert-Butyl N,N’-diisopropylcarbamimidate(cas: 71432-55-8) belongs to anime. Reaction with nitrous acid (HNO2), which functions as an acylating agent that is a source of the nitrosyl group (―NO), converts aliphatic primary amines to nitrogen and mixtures of alkenes and alcohols corresponding to the alkyl group in a complex process. This reaction has been used for analytical determination of primary amino groups in a procedure known as the Van Slyke method.Computed Properties of C11H24N2O

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