Month: October 2022

In 2017,Lin, Tse-Hsueh; Lin, Cin-Hao; Liu, Ying-Jie; Huang, Chun Yi; Lin, Yen-Cheng; Wang, Sheng-Kai published 《Controlling Ligand Spacing on Surface: Polyproline-Based Fluorous Microarray as a Tool in Spatial Specificity Analysis and Inhibitor Development for Carbohydrate-Protein Interactions》.ACS Applied Materials & Interfaces published the findings.Safety of tert-Butyl N,N’-diisopropylcarbamimidate The information in the text is summarized as follows:

Multivalent carbohydrate-protein interactions are essential for many biol. processes. Convenient characterization for multivalent binding property of proteins will aid the development of mols. to manipulate these processes. The authors exploited the polyproline helix II (PPII) structure as mol. scaffolds to adjust the distances between glycan ligand attachment sites at 9, 18, and 27 Å on a peptide scaffold. Optimized fluorous groups were also introduced to the peptide scaffold for immobilization to the microarray surface through fluorous interaction to control the orientation of the helical scaffolds. Using lectin LecA and antibody 2G12 as model proteins, the binding preference to the 27 Å glycopeptide scaffold, matched the distance of 26 Å between its two galactose binding sites on LecA and 31 Å spacing between oligomannose binding sites on 2G12, resp. The authors further demonstrate this microarray system can aid the development of inhibitors by transforming the selected surface-bound scaffold into multivalent ligands in solution This strategy can be extended to analyze proteins that lacking structural information to speed up the design of potent and selective multivalent ligands.tert-Butyl N,N’-diisopropylcarbamimidate(cas: 71432-55-8Safety of tert-Butyl N,N’-diisopropylcarbamimidate) was used in this study.

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.Safety of tert-Butyl N,N’-diisopropylcarbamimidate

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

In 2017,Tamanini, Emiliano; Buck, Ildiko M.; Chessari, Gianni; Chiarparin, Elisabetta; Day, James E. H.; Frederickson, Martyn; Griffiths-Jones, Charlotte M.; Hearn, Keisha; Heightman, Tom D.; Iqbal, Aman; Johnson, Christopher N.; Lewis, Edward J.; Martins, Vanessa; Peakman, Torren; Reader, Michael; Rich, Sharna J.; Ward, George A.; Williams, Pamela A.; Wilsher, Nicola E. published 《Discovery of a Potent Nonpeptidomimetic, Small-Molecule Antagonist of Cellular Inhibitor of Apoptosis Protein 1 (cIAP1) and X-Linked Inhibitor of Apoptosis Protein (XIAP)》.Journal of Medicinal Chemistry published the findings.Formula: C4H9NO2 The information in the text is summarized as follows:

XIAP and cIAP1 are members of the inhibitor of apoptosis protein (IAP) family and are key regulators of anti-apoptotic and pro-survival signaling pathways. Overexpression of IAPs occurs in various cancers and has been associated with tumor progression and resistance to treatment. Structure-based drug design (SBDD) guided by structural information from X-ray crystallog., computational studies, and NMR solution conformational anal. was successfully applied to a fragment-derived lead resulting in AT-IAP, a potent, orally bioavailable, dual antagonist of XIAP and cIAP1 and a structurally novel chem. probe for IAP biol. In the experiment, the researchers used many compounds, for example, N-Methoxy-N-methylacetamide(cas: 78191-00-1Formula: C4H9NO2)

N-Methoxy-N-methylacetamide(cas: 78191-00-1) belongs to anime. Left-handed and right-handed forms (mirror-image configurations, known as optical isomers or enantiomers) are possible when all the substituents on the central nitrogen atom are different (i.e., the nitrogen is chiral). With amines, there is extremely rapid inversion in which the two configurations are interconverted.Formula: C4H9NO2

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

The author of 《Quality by Design (Qbd) Approach to Develop HPLC Method for Estimation of Gliclazide and its Impurity (Gliclazide Impurity A) in Bulk Drug》 were Vijayaraj, Surendran; Palei, Narahari N.; Katyayani, Thummala. And the article was published in Current Pharmaceutical Analysis in 2019. Safety of 4-Methylbenzenesulfonamide The author mentioned the following in the article:

Background: Gliclazide Impurity A (GI-A) is one of the gliclazide impurities, as described in the European Pharmacopoeia. Objective: The objective of this study was to develop and validate simple, robust and accurate Reverse- Phase High-Performance Liquid Chromatog. (RP-HPLC) method for estimation of gliclazide along with GI-A in bulk by optimizing chromatog. parameters using Box Behnken design in response surface methodol. Methods & Results: Box Behnken design was employed for optimizing flow rate, injection volume and strength of the buffer in order to minimize retention time of both gliclazide and GI-A. The optimized strength of orthophosphoric acid buffer in a mixture of Acetonitrile (50:50 volume/volume), flow rate and injection volume were found to be 25mM, 1mL/min, 20μL resp. Linearity was observed in concentration range of 25-150μg/mL (r2=0.999). The retention time of gliclazide and GI-A was found to be 5.799 min and 3.819 min, resp. The limit of detection for Gliclazide and GI-A was found to be 0.0066, and 0.0075μg/mL and the limit of quantification limit was found to be 0.0202, 0.0228μg/mL, resp. The developed method was validated as per the ICH guidelines. Conclusion: The proposed method is useful for best anal. of Gliclazide and GI-A in pharmaceutical dosage forms. QbD approach was found to be an effective tool for optimizing chromatog. conditions of the proposed method.4-Methylbenzenesulfonamide(cas: 70-55-3Safety of 4-Methylbenzenesulfonamide) was used in this study.

4-Methylbenzenesulfonamide(cas: 70-55-3) belongs to anime. Acylation is one of the most important reactions of primary and secondary amines; a hydrogen atom is replaced by an acyl group (a group derived from an acid, such as RCOOH or RSO3H, by removal of ―OH, such as RC(=O)―, RS(O)2―, and so on). Reagents may be acid chlorides (RCOC1, RSO2C1), anhydrides ((RCO)2O), or even esters (RCOOR′); the products are amides of the corresponding acids.Safety of 4-Methylbenzenesulfonamide

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

《Synthesis, docking study and inhibitory activity of 2,6-diketopiperazines derived from α-amino acids on HDAC8》 was published in Bioorganic Chemistry in 2020. These research results belong to Garrido Gonzalez, Flor Paulina; Mancilla Percino, Teresa. COA of Formula: C2H4BrNO The article mentions the following:

Diketopiperazines (DKPs) have been regarded as an important scaffold from the viewpoint of synthesis due to their biol. properties for the treatment of several diseases, including cancer. Two novel series of enantiomeric 2,6-DKPs derived from α-amino acids were synthesized through nucleophilic substitution and intramol. cyclization reactions. All the compounds were docked against histone deacetylase 8 (HDAC8), which was a promising target for the development of anticancer drugs. These compounds bound into the active site of HDAC8 in a similar way to Trichostatin A (TSA), which was an HDAC8 inhibitor. This study showed that the conformation of the 2,6-DKP ring, stereochem., and the type of substituent on the chiral center had an important role in the binding modes. The Gibbs free energies and dissociation constants values of HDAC8-ligand complexes showed that compounds (S)-4hBn, (S)-4m, (R)-4h, and (R)-4m were more stable and affine towards HDAC8 than TSA. The inhibitory activities of 4a, (S)-4h, (S)- and (R)-4(g, l, m) were evaluated in vitro on HDAC8. It was found that compounds (R)-4g (IC50 = 21.54 nM) and (R)-4m (IC50 = 10.81 nM) exhibited better inhibitory activities than TSA (IC50 = 28.32 nM). These results suggested that 2,6-DKPs derivatives may be promising anticancer agents for further biol. studies. The experimental part of the paper was very detailed, including the reaction process of 2-Bromoacetamide(cas: 683-57-8COA of Formula: 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.COA of Formula: C2H4BrNO

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

《Monohaloacetic Acids and Monohaloacetamides Attack Distinct Cellular Proteome Thiols》 was written by Hall, David Ross; Yeung, Kirsten; Peng, Hui. Safety of 2-Bromoacetamide And the article was included in Environmental Science & Technology in 2020. The article conveys some information:

Disinfection byproduct (DBP) exposure has been linked to multiple adverse health outcomes. However, the mol. initiating events by which DBPs induce their toxicities remain unclear. Herein, we combined reporter cell lines and activity-based protein profiling (ABPP) chem. proteomics to identify the protein targets of three monohaloacetic acids (mHAAs) and three monohaloacetamides (mHAMs), at the proteome-wide level. While mHAAs and mHAMs have similar potencies in reducing MTT activity, mHAMs induced greater Nrf2-mediated oxidative stress responses, demonstrating their distinct toxicity pathways. ABPP on crude cell lysates suggested that general proteome thiol reactivity correlates with cytotoxicity. Interestingly, live cell ABPP results revealed class-specific proteins attacked by mHAMs or mHAAs. Subsequent proteomic anal. identified >100 unique targets per DBP. mHAMs preferentially react with redox proteins including disulfide oxidoreductase enzymes, accounting for their stronger Nrf2 responses. To further probe alkylation mechanisms, we directly monitored protein adducts and identified 120 and 37 unique peptides with iodoacetamide and iodoacetic acid adducts, resp. Of the latter, we confirmed glyceraldehyde-3-phosphate dehydrogenase as a key target of IAA, specifically attacking the catalytic Cys 152. This is the first study reporting the distinct cellular protein targets of mHAAs and mHAMs at the proteome-wide level, which highlights their different toxicity pathways despite their similar structures.2-Bromoacetamide(cas: 683-57-8Safety of 2-Bromoacetamide) 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.Safety of 2-Bromoacetamide

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

Reichard, Holly A.; Schiffer, Hans H.; Monenschein, Holger; Atienza, Josephine M.; Corbett, Gerard; Skaggs, Alton W.; Collia, Deanna R.; Ray, William J.; Serrats, Jordi; Bliesath, Joshua; Kaushal, Nidhi; Lam, Betty P.; Amador-Arjona, Alejandro; Rahbaek, Lisa; McConn, Donavon J.; Mulligan, Victoria J.; Brice, Nicola; Gaskin, Philip L. R.; Cilia, Jackie; Hitchcock, Stephen published their research in Journal of Medicinal Chemistry in 2021. The article was titled 《Discovery of TAK-041: a Potent and Selective GPR139 Agonist Explored for the Treatment of Negative Symptoms Associated with Schizophrenia》.Application In Synthesis of N-Methoxy-N-methylacetamide The article contains the following contents:

The chem. optimization that led to the discovery and validation of multiple potent and selective in vivo GPR139 agonist tool compounds, including our clin. candidate TAK-041, also known as NBI-1065846. The pharmacol. characterization of these GPR139 agonists in vivo demonstrated GPR139-agonist-dependent modulation of habenula cell activity and revealed consistent in vivo efficacy to rescue social interaction deficits in the BALB/c mouse strain. The clin. GPR139 agonist TAK-041 was being explored as a novel drug to treat neg. symptoms in SCZ. In the experiment, the researchers used 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. 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.Application In Synthesis of N-Methoxy-N-methylacetamide

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

Moutaoukil, Zakaria; Serrano-Diez, Emmanuel; Collado, Isidro G.; Jimenez-Tenorio, Manuel; Botubol-Ares, Jose Manuel published an article in 2022. The article was titled 《N-Alkylation of organonitrogen compounds catalyzed by methylene-linked bis-NHC half-sandwich ruthenium complexes》, and you may find the article in Organic & Biomolecular Chemistry.Synthetic Route of C7H9NO2S The information in the text is summarized as follows:

An efficient ruthenium-catalyzed N-alkylation of amines, amides and sulfonamides was developed employing novel pentamethylcyclopentadienylruthenium(II) complexes bearing the methylene linked bis(NHC) ligand bis(3-methylimidazol-2-ylidene)methane. The acetonitrile complex I was proved to be particularly effective with a broad range of substrates with low catalyst loading (0.1-2.5 mol%) and high functional group tolerance under mild conditions. A total of 52 N-alkylated organonitrogen compounds including biol. relevant scaffolds were synthesized from (hetero)aromatic and aliphatic amines, amides and sulfonamides using alcs. or diols as alkylating agents in up to 99% isolated yield, even on gram-scale reactions. In the case of sulfonamides, it was the first example of N-alkylation employing a transition-metal complex bearing NHC ligands. In the experiment, the researchers used many compounds, for example, 4-Methylbenzenesulfonamide(cas: 70-55-3Synthetic Route of C7H9NO2S)

4-Methylbenzenesulfonamide(cas: 70-55-3) belongs to anime. The methylamines occur in small amounts in some plants. Many polyfunctional amines (i.e., those having other functional groups in the molecule) occur as alkaloids in plants—for example, mescaline, 2-(3,4,5-trimethoxyphenyl)ethylamine; the cyclic amines nicotine, atropine, morphine, and cocaine; and the quaternary salt choline, N-(2-hydroxyethyl)trimethylammonium chloride, which is present in nerve synapses and in plant and animal cells.Synthetic Route of C7H9NO2S

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

In 2022,Bhattacharjee, Jayeeta; Bockfeld, Dirk; Tamm, Matthias published an article in Journal of Organic Chemistry. The title of the article was 《N-Heterocyclic Carbene-Phosphinidenide Complexes as Hydroboration Catalysts》.Recommanded Product: 2-Bromoacetamide The author mentioned the following in the article:

The reactions of the N-heterocyclic carbene-phosphinidene adducts (NHC)PSiMe3 and (NHC)PH with the dinuclear ruthenium and osmium complexes [(η6-p-cymene)MCl2]2 (M = Ru, Os) afforded the half-sandwich complexes [(η6-p-cymene){(NHC)P}MCl] and [(η6-p-cymene){(NHC)PH}MCl2] with two- and three-legged piano-stool geometries, resp. (NHC = IDipp, IMes; IDipp = 1,3-bis(2,6-diisopropylphenyl)imidazolin-2-ylidene; IMes = 1,3-bis(2,4,6-trimethylphenyl)imidazolin-2-ylidene). The complexes were initially tested as precatalysts for the hydroboration of benzonitrile, and the most active species, the ruthenium complex [(η6-p-cymene){(IMes)P}RuCl], was further used for the efficient hydroboration of a wide range (ca. 50 substrates) of nitriles, carboxylic esters, and carboxamides in neat pinacolborane (HBpin) under comparatively mild reaction conditions (60-80°C, 3-5 mol % catalyst loading). Preliminary mechanistic and kinetic studies are reported, and stoichiometric reactions with HBpin indicate the initial formation of the monohydride complex [(η6-p-cymene){(IMes)P}RuH] as the putative catalytically active species. In the experimental materials used by the author, we found 2-Bromoacetamide(cas: 683-57-8Recommanded Product: 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.Recommanded Product: 2-Bromoacetamide

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

Electric Literature of C4H9NO2In 2020 ,《Preclinical optimization of gp120 entry-antagonists as anti-HIV-1 agents with improved cytotoxicity and ADME properties through rational design, synthesis, and antiviral evaluation》 appeared in Journal of Medicinal Chemistry. The author of the article were Curreli, Francesca; Ahmed, Shahad; Benedict Victor, Sofia M.; Iusupov, Ildar R.; Belov, Dmitry S.; Markov, Pavel O.; Kurkin, Alexander V.; Altieri, Andrea; Debnath, Asim K.. The article conveys some information:

To optimize the structure of previously reported HIV-1 gp120 antagonist NBD-14189 which showed antiviral activity against HIV-1HXB2 (IC50 = 89 nM) but had high cytotoxicity and poor aqueous solubility, a series of novel azaarenyl analogs I [R1 = H, HOCH2, HOCH2CHOH, etc.; R2 = H, HOCH2, HOCH2CHOH; R3, R4, R5 = R6 = H, Me; R7 = 5-chloro-2-pyridinyl, 6-trifluoromethyl-3-pyridazinyl, 5-chloro-2-pyrimidinyl, etc.] have been synthesized and evaluated. One of the new analogs, the compound (S)-I [R1 = H; R2 = HOCH2; R3 = R4 = R5 = H; R6 = Me; R7 = 5-trifluoromethyl-2-pyridinyl; NBD-14270] showed a marked improvement in cytotoxicity, with a 3-fold and 58-fold improvements in SI values compared with that of NBD-14189 and NBD-11021, resp. Furthermore, the in-vitro ADME data clearly showed improvements in aqueous solubility and other properties compared with those for NBD-14189. After reading the article, we found that the author used N-Methoxy-N-methylacetamide(cas: 78191-00-1Electric Literature of C4H9NO2)

N-Methoxy-N-methylacetamide(cas: 78191-00-1) 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.Electric Literature of C4H9NO2

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

Synthetic Route of C11H9N3OOn June 3, 2020, Riascos-Rodriguez, Karina; Marks, Samuel; Evans, Paul G.; Hernandez-Rivera, Samuel P.; Ruiz-Caballero, Jose L.; Pinero, Dalice; Hernandez-Maldonado, Arturo J. published an article in Crystal Growth & Design. The article was 《Lithium Functionalization Promoted by Amide-Containing Ligands of a Cu(pzdc)(pia) Porous Coordination Polymer for CO2 Adsorption Enhancement》. The article mentions the following:

A pillared layer network containing amide functional groups (Cu(pzdc)(pia); pzdc = pyrazine-2,3-dicarboxylate; pia = N-(4-pyridyl)isonicotinamide) was used to test a postsynthesis metalation rationale to insert lithium and create a porous surface with enhanced CO2 adsorption capacity. Synchrotron powder X-ray diffraction (XRD) was used to determine variations after lithiation in long-range and textural properties. CO2 adsorption measurements at room temperature showed a concave up isotherm shape with an increasing adsorption at high pressures, surpassing by 1 order of magnitude the values previously reported for the unmodified material. There was significant hysteresis upon desorption, which suggests structural variations consequent to different or stronger adsorption sites. Results from elemental, thermal gravimetric, and crystal refinement analyses indicate that the lithium content is ca. 3 Li atoms per asym. unit. Raman scattering showed N-Li and Li-O stretching bands, a shift of pia amide- and pyridyl-related bands, and other significant skeletal vibrations associated with nitrogen and oxygen lone pair variations. In situ XRD and CO2 adsorption observations at up to 50 bar at ambient temperature were consistent with the anticipated structural dynamic variation. The lattice changes observed at pressures below 10 bar following lithiation may be directly related to an enhancement in the CO2 adsorption amount The experimental part of the paper was very detailed, including the reaction process of N-(Pyridin-4-yl)isonicotinamide(cas: 64479-78-3Synthetic Route of C11H9N3O)

N-(Pyridin-4-yl)isonicotinamide(cas: 64479-78-3) belongs to amides.Synthetic Route of C11H9N3O 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