Month: October 2022

《Hydrogenative Metathesis of Enynes via Piano-Stool Ruthenium Carbene Complexes Formed by Alkyne gem-Hydrogenation》 was written by Peil, Sebastian; Bistoni, Giovanni; Goddard, Richard; Fuerstner, Alois. Formula: C4H9NO2 And the article was included in Journal of the American Chemical Society in 2020. The article conveys some information:

The only recently discovered gem-hydrogenation of internal alkynes is a fundamentally new transformation, in which both H atoms of dihydrogen are transferred to the same C atom of a triple bond while the other position transforms into a discrete metal carbene complex. [Cp*RuCl]4 is presently the catalyst of choice: the resulting piano-stool ruthenium carbenes can engage a tethered alkene into either cyclopropanation or metathesis, and a prototypical example of such a reactive intermediate with an olefin ligated to the ruthenium center has been isolated and characterized by X-ray diffraction. It is the substitution pattern of the olefin that determines whether metathesis or cyclopropanation takes place: a systematic survey using alkenes of largely different character in combination with a computational study of the mechanism at the local coupled cluster level of theory allowed the preparative results to be sorted and an intuitive model with predictive power to be proposed. This model links the course of the reaction to the polarization of the double bond as well as to the stability of the secondary carbene complex formed, if metathesis were to take place. The first application of “”hydrogenative metathesis”” to the total synthesis of sinularones E and F concurred with this interpretation and allowed the proposed structure of these marine natural products to be confirmed. During this synthesis, it was found that gem-hydrogenation also provides opportunities for C-H functionalization. Moreover, silylated alkynes are shown to participate well in hydrogenative metathesis, which opens a new entry into valuable allylsilane building blocks. Crystallog. evidence suggests that the polarized [Ru-Cl] bond of the catalyst interacts with the neighboring R3Si group. Since attractive interligand Cl/R3Si contacts had already previously been invoked to explain the outcome of various ruthenium-catalyzed reactions, including trans-hydrosilylation, the exptl. confirmation provided herein has implications beyond the present case. 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. 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.Formula: C4H9NO2

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

《Expedient Pd-Catalyzed α-Arylation towards Dibenzoxepinones: Pivotal Manske’s Ketone for the Formal Synthesis of Cularine Alkaloids》 was written by Deichert, Julie A.; Mizufune, Hideya; Patel, Jignesh J.; Hurst, Timothy E.; Maheta, Ashish; Kitching, Mathew O.; Ross, Avena C.; Snieckus, Victor. Category: amides-buliding-blocks And the article was included in European Journal of Organic Chemistry in 2020. The article conveys some information:

The general synthesis of diversely substituted dibenzoxepinones by a combined Pd-catalyzed α-arylation and SNAr strategy is reported and applied to the synthesis of Manske’s ketone, a key intermediate en route to the total synthesis of cularine alkaloids. In the course of this work, an unanticipated ring contraction reaction to a xanthone was observed and serves as a caveat for the conditions of the widely used α-arylation reaction. Thus, e.g., o-(2-bromophenoxy)acetophenone → dibenzoxepinone I (72%) in presence of Pd2(dba)3 and XantPhos, Cs2CO3 as base and toluene as solvent. The results came from multiple reactions, including the reaction of N-Methoxy-N-methylacetamide(cas: 78191-00-1Category: amides-buliding-blocks)

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).Category: amides-buliding-blocks

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

Saito, Takanobu; Caner, Joaquim; Toriumi, Naoyuki; Iwasawa, Nobuharu published their research in Angewandte Chemie, International Edition in 2021. The article was titled 《Rhodium-Catalyzed meta-Selective C-H Carboxylation Reaction of 1,1-Diarylethylenes via Hydrorhodation-Rhodium Migration》.COA of Formula: C4H9NO2 The article contains the following contents:

A meta-selective C-H carboxylation reaction of 1,1-diarylethylene derivatives with CO2 by using a rhodium catalyst with NaOiPr as a stoichiometric reductant has been achieved. Together with hydrogenation of the ethylene moiety, a carboxyl group was introduced to the meta-position of the aryl ring with high selectivity over the ortho-positions. Exptl. and computational mechanistic studies indicate that this carboxylation reaction proceeds via hydrorhodation on the ethylene moiety, followed by 1,4-rhodium migration and successive 1,2-rhodium migration on the aryl ring. The use of a bulky phosphine ligand seems to be the key to this unusual aryl-to-aryl 1,2-rhodium shift. The experimental process involved the reaction of N-Methoxy-N-methylacetamide(cas: 78191-00-1COA of Formula: C4H9NO2)

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

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

In 2022,Cheng, Jin-Tang; Xiao, Li-Jun; Qian, Shao-Qun; Zhuang, Zhe; Liu, An; Yu, Jin-Quan published an article in Angewandte Chemie, International Edition. The title of the article was 《Palladium(II)-Catalyzed Selective Arylation of Tertiary C-H Bonds of Cyclobutylmethyl Ketones Using Transient Directing Groups》.Category: amides-buliding-blocks The author mentioned the following in the article:

Authors report the first example of selective PdII-catalyzed tertiary C-H activation of cyclobutylmethyl ketones using a transient directing group. An electron-deficient 2-pyridone ligand was identified as the optimal external ligand to enable tertiary C-H activation. A variety of cyclobutylmethyl ketones bearing quaternary carbon centers was readily accessed without preinstalling internal directing groups in up to 81% yield and >95 : 5 regioisomeric ratios of tertiary C-H arylation to β-methylene (β-methyl) or γ-C-H arylation. In the experiment, the researchers used many compounds, for example, N-Methoxy-N-methylacetamide(cas: 78191-00-1Category: amides-buliding-blocks)

N-Methoxy-N-methylacetamide(cas: 78191-00-1) belongs to anime. Large quantities of aliphatic amines are made synthetically. The most widely used industrial method is the reaction of alcohols with ammonia at a high temperature, catalyzed by metals or metal oxide catalysts (e.g., nickel or copper). Mixtures of primary, secondary, and tertiary amines are thereby produced.Category: amides-buliding-blocks

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

Safety of 2-BromoacetamideIn 2022 ,《Supramolecular Enhancement of Antenna-sensitized Europium(III) Luminescence by Cucurbit[7]uril Complexation》 was published in European Journal of Inorganic Chemistry. The article was written by Matsumoto, Masaomi; Reid, Jon; Byeman, Connor; Evbuomwan, Osasere. The article contains the following contents:

The authors report the supramol. complexation of an antenna-sensitized DOTAM-Eu complex with Cucurbit[7]uril (CB[7]), via the inclusion of the antenna moiety in the CB[7] cavity, observed through UV-visible and NMR spectroscopy. Eu luminescence quantum yield is enhanced by CB[7] complexation of the antenna. The photophysics of the analogous DOTAM-Gd complex was studied to elucidate the mechanism by which antenna-inclusion leads to supramol. luminescence enhancement. The authors report supramol. enhancement of Eu-ligand complex stability.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

SDS of cas: 106392-48-7On March 25, 1988, Shiraishi, Tadayoshi; Kameyama, Keiji; Imai, Naohiro; Domoto, Takeshi; Katsumi, Ikuo; Watanabe, Kiyoshi published an article in Chemical & Pharmaceutical Bulletin. The article was 《Specific inhibitors of tyrosine-specific protein kinase. I. Synthesis and inhibitory activities of α-cyanocinnamamides》. The article mentions the following:

A series of α-cyanocinnamamide derivatives was synthesized and evaluated for inhibitory activity against tyrosine-specific protein kinase of intact plasma membrane fractions from an epidermoid carcinoma cell line, A-431. Among these compounds, several novel α-cyano-4-hydroxy-3,5-disubstituted cinnamamide derivatives, e.g., ST 638 (I) showed potent inhibitory activity. The studies on the structure-activity relationship revealed that the presence of the OH group at the 4 position and the double bond in the α-cyano-4-hydroxycinnamamide skeleton were important for potent inhibitory activity, and that the presence of hydrophobic groups at the 3 and 5 positions on the benzene ring also enhanced the inhibitory activity of α-cyano-4-hydroxycinnamamide derivatives In the experimental materials used by the author, we found 2-Cyano-3-(4-hydroxy-3,5-diisopropylphenyl)acrylamide(cas: 106392-48-7SDS of cas: 106392-48-7)

2-Cyano-3-(4-hydroxy-3,5-diisopropylphenyl)acrylamide(cas: 106392-48-7) belongs to amides.SDS of cas: 106392-48-7 The solubilities of amides and esters are roughly comparable. Typically amides are less soluble than comparable amines and carboxylic acids since these compounds can both donate and accept hydrogen bonds.

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

Category: amides-buliding-blocksOn October 1, 2021 ,《Synthesis, antitumor activity and in silico analyses of amino acid derivatives of artepillin C, drupanin and baccharin from green propolis》 was published in Bioorganic & Medicinal Chemistry. The article was written by Rodrigues, Debora Munhoz; Portapilla, Gisele Bulhoes; Silva, Guilherme Martins; Duarte, Andressa; Rotta, Cristiana Goncalez; da Silva, Carlos Henrique Tomich de Paula; de Albuquerque, Sergio; Bastos, Jairo Kenupp; Campo, Vanessa Leiria. The article contains the following contents:

Breast cancer has the highest incidence and mortality in females, while prostate cancer has the second-highest incidence in males. Studies have shown that compounds from Brazilian green propolis have antitumor activities and can selectively inhibit the AKR1C3 enzyme, overexpressed in hormone-dependent prostate and breast tumors. Thus, in an attempt to develop new cytotoxic inhibitors against these cancers, three prenylated compounds, artepillin C, drupanin and baccharin, were isolated from green propolis to synthesize new derivatives via coupling reactions with different amino acids. All obtained derivatives were submitted to antiproliferative assays against four cancer cells (MCF-7, MDA MB-231, PC-3, and DU145) and two normal cell lines (MCF-10A and PNT-2) to evaluate their cytotoxicity. In general, the best activity was observed for compound 6e, derived from drupanin, which exhibited half-maximal inhibitory concentration (IC50) of 9.6 ± 3 μM and selectivity index (SI) of 5.5 against MCF-7 cells. In silico studies demonstrated that these derivatives present coherent docking interactions and binding modes against AKR1C3, which might represent a possible mechanism of inhibition in MCF-7 cells. The results came from multiple reactions, including the reaction of H-Lys(Boc)-OH(cas: 2418-95-3Category: amides-buliding-blocks)

H-Lys(Boc)-OH(cas: 2418-95-3) belongs to amino acids. These amino acids may be present in low concentrations and play a vital part as an intermediate in a biosynthetic pathway, e.g., ornithine, homoserine, or cystathionine. In contrast they may act as a major storage form of nitrogen, e.g., canavanine in the seed of Canavalia ensiformis, or may be formed in high amounts in response to an external stress, e.g., γ-aminobutyrate.Category: amides-buliding-blocks It is possible that some of these nonprotein amino acids may serve as insecticidal or fungicidal agents.

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

HPLC of Formula: 87694-50-6On May 5, 1998 ,《The design and synthesis of inhibitors of the cysteinyl protease, Der p I》 appeared in Bioorganic & Medicinal Chemistry Letters. The author of the article were Billson, Jeremy; Clark, Jonathan; Conway, Simon P.; Hart, Terance; Johnson, Tony; Langston, Steven P.; Ramjee, Manoj; Quibell, Martin; Scott, Richard K.. The article conveys some information:

Prototype irreversible inhibitors I [R = H, Me3CO2C (Boc), Ac, Bz, R1 = CO2Et; R = Boc, R1 = SO2Me, SO2CH2Ph, SO2Ph] and II (R2 = H, Me, Cl, CF3) of the cysteinyl protease Der p I were designed, synthesized and evaluated in vitro. Candidates were designed using a modular approach, whereby a peptide sequence was appended with known thiophilic moieties. This hinged on utilizing peptide sequences from substrate specificity data compiled using proprietary RAPiD technol. The experimental process involved the reaction of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6HPLC of Formula: 87694-50-6)

(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.HPLC of Formula: 87694-50-6 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

Hooper, Joel F.; Seo, Sangwon; Truscott, Fiona R.; Neuhaus, James D.; Willis, Michael C. published an article on February 10 ,2016. The article was titled 《α-Amino Aldehydes as Readily Available Chiral Aldehydes for Rh-Catalyzed Alkyne Hydroacylation》, and you may find the article in Journal of the American Chemical Society.SDS of cas: 87694-50-6 The information in the text is summarized as follows:

Readily available α-amino aldehydes, incorporating a methylthiomethyl (MTM) protecting group on nitrogen, are shown to be efficient substrates in Rh-catalyzed alkyne hydroacylation reactions. The reactions are performed under mild conditions, employing a small-bite-angle bis-phosphine ligand, allowing for good functional group tolerance with high stereospecificity. Amino aldehydes derived from glycine, alanine, valine, leucine, phenylalanine, isoleucine, serine, tryptophan, methionine, and cysteine were successfully employed, as was an enantiomerically enriched α-OMTM-aldehyde derived from phenyllactic acid. The synthetic utility of the α-amino enone products is demonstrated in a short enantioselective synthesis of the natural product sphingosine. After reading the article, we found that the author used (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6SDS of cas: 87694-50-6)

(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) belongs to amides. The solubilities of amides and esters are roughly comparable. Typically amides are less soluble than comparable amines and carboxylic acids since these compounds can both donate and accept hydrogen bonds.SDS of cas: 87694-50-6

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

Lescop, Cyrille; Herzner, Holger; Siendt, Herve; Bolliger, Reto; Henneboehle, Marco; Weyermann, Philipp; Briguet, Alexandre; Courdier-Fruh, Isabelle; Erb, Michael; Foster, Mark; Meier, Thomas; Magyar, Josef P.; Von Sprecher, Andreas published their research in Bioorganic & Medicinal Chemistry Letters on December 1 ,2005. The article was titled 《Novel cell-penetrating α-keto-amide calpain inhibitors as potential treatment for muscular dystrophy》.Electric Literature of C13H26N2O4 The article contains the following contents:

Dipeptide-derived α-keto-amide compounds, e.g., I, with potent calpain inhibitory activity have been identified. These reversible covalent inhibitors have IC50 values down to 25 nM and exhibit greatly improved activity in muscle cells compared to the reference compound MDL28170. Several novel calpain inhibitors have shown pos. effects on histol. parameters in an animal model of Duchenne muscular dystrophy demonstrating their potential as a treatment option for this fatal disease. In the part of experimental materials, we found many familiar compounds, such as (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Electric Literature of C13H26N2O4)

(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. Electric Literature of C13H26N2O4

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