Category: amides-buliding-blocks

《Synthesis of Nα-protected amino acid/peptide Weinreb amides employing N,N’-carbonyldiimidazole as activating agent; studies on docking and antibacterial activities》 was written by Uma, K.; Lalithamba, H. S.; Raghavendra, M.; Chandramohan, Vivek; Anupama, C.. Application In Synthesis of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide And the article was included in ARKIVOC (Gainesville, FL, United States) in 2016. The article conveys some information:

An efficient method for the synthesis of Nα-protected amino/peptide Weinreb amides (N-methoxy-N-methylamides) employing N,N’-carbonyldiimidazole (CDI) has been achieved. Nα-protected amino/peptide acids were treated with N,N’-carbonyldiimidazole, followed by the addition of N,O-dimethylhydroxylamine hydrochloride salt to yield the desired compounds The synthesized compounds were mainly gums, a few were solids, after the simple workup, and were characterized by IR, 1H NMR, 13C NMR and HRMS. The Weinreb amides were subjected to in silico studies, to predict the preferred orientation and binding affinity between the mols. using scoring functions. The ligand N-Fmoc-L-Phe-N(OCH3)CH3 showed min. binding energy – 29.85 kcal/mol with Escherichia coli and the ligand N-Fmoc-L-Ala-N(OCH3)CH3 showed min. binding energy -24.79 kcal/mol with Pseudomonas aeruginosa, -25.01 kcal/mol with Staphylococcus aureus. Based on the min. binding energies, antibacterial activities have been conducted for a few of the synthesized compounds In the experiment, the researchers used many compounds, for example, (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.Application In Synthesis of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide 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

《Solvent interception, heterocyclization and desilylation upon NBS-induced sulfamidation of trimethyl(vinyl)silane》 was written by Astakhova, Vera V.; Moskalik, Mikhail Yu.; Shainyan, Bagrat A.. Product Details of 70-55-3This research focused onthree component amidation bromination vinylsilane sulfonamide aziridine preparation; Ritter reaction acetonitrile vinylsilane bromosuccinimide sulfonamide preparation imidazole; oxazocine preparation Ritter reaction acetonitrile bromoalkylsilane. The article conveys some information:

Silylated N-bromoethylsulfonamides, aziridines, imidazoles and oxazocane were prepared by three-component reaction of vinylsilane with brominating agents and sulfonamides with participation of solvent acetonitrile. The reaction of trimethyl(vinyl)silane with sulfonamides in the presence of N-bromosuccinimide was shown to proceed regioselectively in methylene chloride under mild conditions and led to the products of bromosulfamidation in up to 88% yield. The obtained adducts undergo base-promoted dehydrobromination to give 2-trimethylsilyl-N-sulfonyl aziridines in a close to quant. yield. In the reaction with trifluoromethanesulfonamide in acetonitrile or THF, the Ritter-type (solvent-interception) products were obtained and converted to 1-triflyl-2-methyl-5-(trimethylsilyl)-2-imidazoline or 4-triflyl-3-(trimethylsilyl)-1,4-oxazocane in almost quant. yield. In the experimental materials used by the author, we found 4-Methylbenzenesulfonamide(cas: 70-55-3Product Details of 70-55-3)

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

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

《LMP2 Inhibitors as a Potential Treatment for Alzheimer’s Disease》 was written by Bhattarai, Deepak; Lee, Min Jae; Baek, Ahruem; Yeo, In Jun; Miller, Zachary; Baek, Yu Mi; Lee, Sukyeong; Kim, Dong-Eun; Hong, Jin Tae; Kim, Kyung Bo. Recommanded Product: 87694-50-6 And the article was included in Journal of Medicinal Chemistry on April 9 ,2020. The article conveys some information:

The immunoproteasome (iP), an inducible proteasome variant harboring three immunosubunits, low mol. mass polypeptide-2 (LMP2), multicatalytic endopeptidase complex subunit-1, and low mol. mass polypeptide-7 (LMP7), is involved in multiple facets of inflammatory responses. We recently reported that YU102, a dual inhibitor of the iP subunit LMP2 and the constitutive proteasome catalytic subunit β1, ameliorates cognitive impairments in mouse models of Alzheimer’s disease (AD) independently of amyloid deposits. To investigate whether inhibition of LMP2 is sufficient to improve the cognitive functions of AD mice, here we prepared 37 YU102 analogs and identified a potent LMP2 inhibitor DB-310 (28) (IC50: 80.6 nM) with improved selectivity and permeability in cells overexpressing ABCB1 transporters. We show that DB-310 induces suppression of IL-1α production in microglia cells and improves cognitive functions in the Tg2576 transgenic mouse model of AD. This study supports that inhibition of LMP2 is a promising therapeutic strategy for treatment of AD. The experimental process involved 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: 87694-50-6Amides 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

Recommanded Product: 4-MethylbenzenesulfonamideIn 2019 ,《Targeted Therapy for Interfacial Engineering Toward Stable and Efficient Perovskite Solar Cells》 was published in Advanced Materials (Weinheim, Germany). The article was written by Wang, Shuhui; Chen, Haiyang; Zhang, Jiandong; Xu, Guiying; Chen, Weijie; Xue, Rongming; Zhang, Moyao; Li, Yaowen; Li, Yongfang. The article contains the following contents:

The poor long-term stability of organic-inorganic hybrid halide perovskite solar cells (pero-SCs) remains a big challenge for their commercialization. Although strategies such as encapsulation, doping, and passivation have been reported, there remains a lack of understanding of the water resistance and thermal stability of pero-SCs. A fullerene derivative, [6,6]-phenyl-C61-butyric acid-N,N-dimethyl-3-(2-thienyl)propanam ester (PCBB-S-N) containing a functional S atom and C60, is synthesized and used as electron transporting layer (ETL)/intermediary layer to targetedly heal the multitype defects in pero-SCs or assist the growth of ETL, such as [6,6]-phenyl-C61-butyric acid Me ester (PCBM), in planar p-i-n pero-SCs. The repaired pero-SCs can not only dramatically improve their power conversion efficiencies, but also address stability issues under moisture and high temperature The corresponding mechanism of PCBB-S-N with targeted therapy effect in a device is systematically studied by both experiments and theor. calculation This work demonstrates that the proposed fullerene derivative with finely tuned chem. structure can be a promising ETL candidate or intermediary to approach stable and efficient planar p-i-n pero-SCs. In addition to this study using 4-Methylbenzenesulfonamide, there are many other studies that have used 4-Methylbenzenesulfonamide(cas: 70-55-3Recommanded Product: 4-Methylbenzenesulfonamide) was used in this study.

4-Methylbenzenesulfonamide(cas: 70-55-3) belongs to anime. Many important products require amines as part of their syntheses. Methylamine is utilized in the production of the analgesic meperidine (trade name Demerol) and the photographic developer Metol (trademark), and dimethylamine is used in the synthesis of the antihistamine diphenhydramine (trade name Benadryl), the solvent dimethylformamide (DMF), and the rocket propellant 1,1-dimethylhydrazine. The synthesis of the insect repellent N,N-diethyl-m-toluamide (DEET) incorporates diethylamine while that of the synthetic fibre Kevlar requires aromatic amines.Recommanded Product: 4-Methylbenzenesulfonamide

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

Application of 70-55-3In 2019 ,《Rh(III)-Catalyzed Direct Amination of Aromatic Ketoximes Enabled by Potassium Acetate》 was published in European Journal of Organic Chemistry. The article was written by Liu, Lingling; Wang, Ning; Dai, Chenyang; Han, Yi; Yang, Shan; Huang, Zhibin; Zhao, Yingsheng. The article contains the following contents:

A method to achieve rhodium(III)-catalyzed, potassium acetate enabled intermol. C-H amination of ketoximes using various benzenesulfonamide, especially 4-nitrobenzenesulfonamide is reported. Various aryl ketoximes substituted with electron-withdrawing functional groups were all well tolerated and produced the corresponding products in moderate to good yields. A preliminary mechanistic study revealed that potassium acetate is essential to realizing intermol. amination. In addition to this study using 4-Methylbenzenesulfonamide, there are many other studies that have used 4-Methylbenzenesulfonamide(cas: 70-55-3Application of 70-55-3) was used in this study.

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.Application of 70-55-3

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

Name: tert-Butyl N,N’-diisopropylcarbamimidateIn 2010 ,《A New Arylsulfate Sulfotransferase Involved in Liponucleoside Antibiotic Biosynthesis in Streptomycetes》 was published in Journal of Biological Chemistry. The article was written by Kaysser, Leonard; Eitel, Kornelia; Tanino, Tetsuya; Siebenberg, Stefanie; Matsuda, Akira; Ichikawa, Satoshi; Gust, Bertolt. The article contains the following contents:

Sulfotransferases are involved in a variety of physiol. processes and typically use 3′-phosphoadenosine 5′-phosphosulfate (PAPS) as the sulfate donor substrate. In contrast, microbial arylsulfate sulfotransferases (ASSTs) are PAPS-independent and utilize arylsulfates as sulfate donors. Yet, their genuine acceptor substrates are unknown. In this study we demonstrate that Cpz4 from Streptomyces sp. MK730-62F2 is an ASST-type sulfotransferase responsible for the formation of sulfated liponucleoside antibiotics. Gene deletion mutants showed that cpz4 is required for the production of sulfated caprazamycin derivatives Cloning, overproduction, and purification of Cpz4 resulted in a 58-kDa soluble protein. The enzyme catalyzed the transfer of a sulfate group from p-nitrophenol sulfate (Km 48.1 μM, kcat 0.14 s-1) and Me umbelliferone sulfate (Km 34.5 μM, kcat 0.15 s-1) onto phenol (Km 25.9 and 29.7 mM, resp.). The Cpz4 reaction proceeds by a ping pong bi-bi mechanism. Several structural analogs of intermediates of the caprazamycin biosynthetic pathway were synthesized and tested as substrates of Cpz4. Des-N-methyl-acyl-caprazol was converted with highest efficiency 100 times faster than phenol. The fatty acyl side chain and the uridyl moiety seem to be important for substrate recognition by Cpz4. Liponucleosides, partially purified from various mutant strains, were readily sulfated by Cpz4 using p-nitrophenol sulfate. No product formation could be observed with PAPS as the donor substrate. Sequence homol. of Cpz4 to the previously examined ASSTs is low. However, numerous orthologs are encoded in microbial genomes and represent interesting subjects for future investigations. In the experiment, the researchers used tert-Butyl N,N’-diisopropylcarbamimidate(cas: 71432-55-8Name: 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.Name: tert-Butyl N,N’-diisopropylcarbamimidate

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

Fulo, Harvey F.; Rueb, Nicole J.; Gaston, Robert Jr.; Batsomboon, Paratchata; Ahmed, Kh Tanvir; Barrios, Amy M.; Dudley, Gregory B. published an article in 2021. The article was titled 《Synthesis of illudalic acid and analogous phosphatase inhibitors》, and you may find the article in Organic & Biomolecular Chemistry.SDS of cas: 78191-00-1 The information in the text is summarized as follows:

Here authors validate a two-step process-convergent [4+2] benzannulation and one-pot coordinated functional group manipulations-for preparing the key trifunctional pharmacophore of illudalic acid. The modular building blocks are readily available in 2-3 steps, for a longest linear sequence (LLS) of 5 steps to illudalic acid from 3,3-dimethylcyclopentanone. A small collection of analogous indanes and tetralins featuring the same pharmacophore were prepared by a similar route. These compounds potently and selectively inhibit the human leukocyte common antigen-related (LAR) subfamily of protein tyrosine phosphatases (PTPs). Evidence supporting a postulated covalent ligation mechanism is provided herein. In addition to this study using N-Methoxy-N-methylacetamide, there are many other studies that have used N-Methoxy-N-methylacetamide(cas: 78191-00-1SDS of cas: 78191-00-1) was used in this study.

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.SDS of cas: 78191-00-1

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

《Crosslinking of a Single Poly(ionic liquid) by Water into Porous Supramolecular Membranes》 was published in Angewandte Chemie, International Edition in 2020. These research results belong to Shao, Yue; Wang, Yong-Lei; Li, Xiangshuai; Kheirabad, Atefeh Khorsand; Zhao, Qiang; Yuan, Jiayin; Wang, Hong. Synthetic Route of C2H4BrNO The article mentions the following:

Reversible regulation of membrane microstructures via non-covalent interactions is of considerable interest yet remains a challenge. Herein, we discover a general one-step approach to fabricate supramol. porous polyelectrolyte membranes (SPPMs) from a single poly(ionic liquid) (PIL). The exptl. results and theor. simulation suggested that SPPMs were formed by a hydrogen-bond-induced phase separation of a PIL between its polar and apolar domains, which were linked together by water mols. This unique feature was capable of modulating microscopic porous architectures and thus the global mech. property of SPPMs by a rational design of the mol. structure of PILs. Such SPPMs could switch porosity upon thermal stimuli, as exemplified by dynamically adaptive transparency to thermal fluctuation. This finding provides fascinating opportunities for creating multifunctional SPPMs. In the experimental materials used by the author, we found 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

The author of 《A Condensation/Reductive Alkylation/Hydrogenation Cascade for Facile Synthesis of Chiral 2,3-Disubstituted Indolines》 were Yu, Chang-Bin; Li, Xiang; Zhou, Yong-Gui. And the article was published in Asian Journal of Organic Chemistry in 2019. COA of Formula: C4H9NO2 The author mentioned the following in the article:

A divergent and enantioselective procedure for synthesis of 2,3-disubstituted indolines was developed through Bronsted acid/palladium-complex promoted condensation/reductive alkylation/ hydrogenation cascade reactions from simple amino ketones and aldehydes in one-pot operation. Five Bronsted acid-promoted steps and two Pd-catalyzed hydrogenation steps were involved in this process. This strategy provided facile synthesis of structurally diverse multi-substituted chiral indolines. In addition to this study using N-Methoxy-N-methylacetamide, there are many other studies that have used N-Methoxy-N-methylacetamide(cas: 78191-00-1COA of Formula: C4H9NO2) was used in this study.

N-Methoxy-N-methylacetamide(cas: 78191-00-1) 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.COA of Formula: C4H9NO2

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

The author of 《Discovery of novel indolylarylsulfones as potent HIV-1 NNRTIs via structure-guided scaffold morphing》 were Zhao, Tong; Meng, Qing; Kang, Dongwei; Ji, Jianbo; De Clercq, Erik; Pannecouque, Christophe; Liu, Xinyong; Zhan, Peng. And the article was published in European Journal of Medicinal Chemistry in 2019. Safety of 2-Bromoacetamide The author mentioned the following in the article:

For more in-depth exploration of the chem. space around the entrance channel of HIV-1 reverse transcriptase (RT), a series of novel indolylarylsulfones (IASs) bearing different chiral N-substituted pyrrolidines (R/S)-I [R1 = methanesulfonyl, pyridin-3-ylmethyl, (2-fluorophenyl)methyl, (4-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl, etc.], azetidines II or substituted sulfonamide groups III [R2 = 2-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)ethyl, ethanesulfonyl, cyclopropanesulfonyl, etc.] at indole-2-carboxamide were designed and synthesized as potent HIV NNRTIs by structure-guided scaffold morphing approach. All the IASs exhibited moderate to excellent potency against wild-type HIV-1 with EC50values ranging from 0.0043 μM to 4.42 μM. Notably, compound (R)-I (R1 = methanesulfonyl) (EC50 = 4.7 nM, SI = 5183) and (S)-I (R1 = methanesulfonyl) (EC50 = 4.3 nM, SI = 7083) were identified as the most potent compounds, which were more active than nevirapine, lamivudine and efavirenz, and also reached the same order of etravirine. Furthermore, some compounds maintained excellent activity against various single HIV-1 mutants (L100I, K103 N, E138K, Y181C) as well as one double mutant (F227L/V106A) with EC50 values in low-micromolar concentration ranges. Notably, II (R2 = carbamoylmethyl) displayed outstanding potency against F227L/V106A (EC50 = 0.094 μM), and also showed exceptional activity against E138K (EC50 = 0.014 μM), L100I (EC50 = 0.011 μM) and K103 N (EC50 = 0.025 μM). Addnl., most compounds showed markedly reduced cytotoxicity (CC50) compared to lead compounds, especially II [R2 = (2-cyanophenyl)methyl] (CC50 >234.91 μM, SI >18727) and II (R2 = methanesulfonyl) (CC50 >252.49 μM, SI >15152). Preliminary SARs and mol. modeling studies were also discussed in detail, which may provide valuable insights for further optimization. In the part of experimental materials, we found many familiar compounds, such as 2-Bromoacetamide(cas: 683-57-8Safety of 2-Bromoacetamide)

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.Safety of 2-Bromoacetamide

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