Category: amides-buliding-blocks

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

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 2014,Huerta, Elisa; van Genabeek, Bas; Stals, Patrick J. M.; Meijer, E. W.; Palmans, Anja R. A. published 《A Modular Approach to Introduce Function into Single-Chain Polymeric Nanoparticles》.Macromolecular Rapid Communications published the findings.Application of 71432-55-8 The information in the text is summarized as follows:

Here, a modular approach is reported to introduce a specific function into single-chain polymeric nanoparticles (SCPNs). Hereto, an amphiphilic polymer with pendant benzene-1,3,5-tricarboxamide (BTA) units is mixed with a “”free”” BTA that contains a functional group, either a fluorescent naphthalimide or a catalytically active l-proline. Taking advantage of hydrophobic interactions and self-recognition properties of the BTA units, the “”free”” BTAs are captured into the interior of the SCPN in water as evidenced by fluorescence studies. To illustrate that function can be readily introduced using a modular approach, l-proline-based BTAs are incorporated to procure a catalytically active SCPN in water. The aldol reaction between p-nitrobenzaldehyde and cyclohexanone shows good conversions at low catalyst loadings and substrate concentrations, and high stereoselectivities are obtained (de = 91% and ee = 98%). The experimental process involved the reaction of tert-Butyl N,N’-diisopropylcarbamimidate(cas: 71432-55-8Application of 71432-55-8)

tert-Butyl N,N’-diisopropylcarbamimidate(cas: 71432-55-8) 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.Application of 71432-55-8

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

Application In Synthesis of 2,2-Dimehtyl-N-pyridin-3-yl-propionamideOn September 30, 1990 ,《Synthesis of 3-amino-4-phenylpyridines: a novel strategy for the preparation of CD ring models of streptonigrin》 was published in Journal of the Chemical Society. The article was written by Marsais, Francis; Rovera, Jean Claude; Turck, Alain; Godard, Alain; Queguiner, Guy. The article contains the following contents:

3-Amino-4-phenylpyridine derivatives were prepared 3-Pivaloylaminopyridines were lithiated by BuLi before reaction with iodine as electrophile to afford 4-iodo-3-pivaloylaminopyridines. Cross-coupling of the latter with suitable phenylboronic acids gives CD ring models e.g. I, of streptonigrin. In addition to this study using 2,2-Dimehtyl-N-pyridin-3-yl-propionamide, there are many other studies that have used 2,2-Dimehtyl-N-pyridin-3-yl-propionamide(cas: 70298-88-3Application In Synthesis of 2,2-Dimehtyl-N-pyridin-3-yl-propionamide) was used in this study.

2,2-Dimehtyl-N-pyridin-3-yl-propionamide(cas: 70298-88-3) 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.Application In Synthesis of 2,2-Dimehtyl-N-pyridin-3-yl-propionamide

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

The author of 《Psychotropic drugs. 18. Synthesis and structure-activity relations of 5-phenyl-1,3-dihydro-2H-thieno[2,3-e][1,4]diazepin-2-ones》 were Nakanishi, Michio; Tahara, Tetsuya; Araki, Kazuhiko; Shiroki, Masami; Tsumagari, Tatsumi; Takigawa, Yukio. And the article was published in Journal of Medicinal Chemistry in 1973. Category: amides-buliding-blocks The author mentioned the following in the article:

Several thienodiazepinones showed central nervous depressant activity in mice comparable to that of diazepam. One of the most active compounds, 5-o-fluorophenyl-7-ethyl-1,3-dihydro-2H-thieno[2,3-e][1,4]diazepin-2-one (I) [41191-07-5], inhibited fighting at 0.4 mg/kg orally and counteracted the lethal effects of pentetrazole at 0.3 mg/kg i.p. Some compounds, including I, also showed anticonvulsant, muscle-relaxant, and narcotic-potentiating activity in mice and a taming effect in olfactory bulbectomized rats. To synthesize I, o-fluoro-ω-cyanoacetophenone [31915-26-1] was condensed with butyraldehyde [123-72-8] and powd. S in DMF-NEt3 to form 2-amino-3-o-fluorobenzoyl-5-ethylthiophene [41191-09-7], converted to 2-chloroacetamido-3-o-fluorobenzoyl-5-ethylthiophene [41191-10-0] by reaction with ClCH2COCl, then to the iodoacetamido compound by exchange with NaI and to the aminoacetamido compound with NH3 gas, and cyclized by refluxing in pyridine-AcOH-C6H6. In the experiment, the researchers used 2-Amino-N-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)acetamide(cas: 50509-09-6Category: amides-buliding-blocks)

2-Amino-N-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)acetamide(cas: 50509-09-6) belongs to anime. Reduction of nitro compounds, RNO2, by hydrogen or other reducing agents produces primary amines cleanly (i.e., without a mixture of products), but the method is mostly used for aromatic amines because of the limited availability of aliphatic nitro compounds. Reduction of nitriles and oximes (R2C=NOH) also yields primary amines.Category: amides-buliding-blocks

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

The author of 《Coordination-driven self-assembly of 2D-metallamacrocycles using a shape-selective PtII2-organometallic 90° acceptor: design, synthesis and sensing study》 were Shanmugaraju, Sankarasekaran; Samanta, Dipak; Gole, Bappaditya; Mukherjee, Partha Sarathi. And the article was published in Dalton Transactions in 2011. Reference of N-(Pyridin-4-yl)isonicotinamide The author mentioned the following in the article:

Synthesis of two-dimensional metallamacrocycles via coordination-driven self-assembly of a shape-selective Pt(II)2-mol. building unit incorporating carbazole-ethynyl functionality is described. An equimolar (1:1) combination of a Pt(II)2-organometallic 90° acceptor, 3,6-bis[trans-Pt(PEt3)2(NO3)(ethynyl)]carbazole (1), with rigid linear ditopic donors La (La = 4,4′-bipyridine) and Lb (Lb = trans-1,2-bis(4-pyridyl)ethylene) afforded the corresponding [4 + 4] self-assembled octanuclear mol. squares in quant. yields. Conversely, a similar treatment of 1 with amide-based unsym. flexible ditopic donor, Lc (Lc = N-(4-pyridyl)isonicotinamide), gave a [2 + 2] self-sorted mol. rhomboid as a single product. Despite the possibility of several linkage isomeric macrocycles (rhomboid, triangle and square) due to the different connectivity of Lc, the formation of a single and sym. mol. rhomboid as the only product is an interesting observation. All the self-assembled macrocycles were fully characterized by multinuclear NMR (1H and 31P) and ESI-MS anal. Further structural insights about the size and shape of the macrocycles were obtained through energy minimization using d. functional theory (DFT) calculations Decoration of the starting carbazole building unit with Pt-ethynyl functionality enriches the assemblies to be more π-electron rich and luminescent in nature. The two octanuclear mol. squares could sense the presence of electron deficient nitroaroms. in solution by fluorescence quenching of the initial intensity upon addition They exhibited the largest quenching response with high selectivity for nitroaroms. compared to several other electron deficient aromatics tested. In the experiment, the researchers used many compounds, for example, N-(Pyridin-4-yl)isonicotinamide(cas: 64479-78-3Reference of N-(Pyridin-4-yl)isonicotinamide)

N-(Pyridin-4-yl)isonicotinamide(cas: 64479-78-3) 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.Reference of N-(Pyridin-4-yl)isonicotinamide

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

Sin, Ny; Kim, Kyung Bo; Elofsson, Mikael; Meng, Lihao; Auth, Hak; Kwok, Benjamin H. B.; Crews, Craig M. published their research in Bioorganic & Medicinal Chemistry Letters on August 2 ,1999. The article was titled 《Total synthesis of the potent proteasome inhibitor epoxomicin: a useful tool for understanding proteasome biology》.Formula: C13H26N2O4 The article contains the following contents:

Epoxomicin (I), a peptide α’,β’-epoxy-ketone isolated from the actinomycete strain NumberQ996-17, possesses potent in vivo anti-tumor and anti-inflammatory activities. The authors report the first syntheses of I, [3H]-I , and a biotinylated I analog as well as the absolute configuration of the epoxide stereo-center. The natural product and derivatives have permitted the first identification of the proteasome as the specific cellular target of I. In the experimental materials used by the author, we found (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Formula: C13H26N2O4)

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

Okada, Yoshio; Taguchi, Hiroaki; Yokoi, Toshio published their research in Chemical & Pharmaceutical Bulletin on December 31 ,1996. The article was titled 《Amino acids and peptides. XLVII. Facile synthesis of flavacol, deoxymuta-aspergillic acid and optically active deoxyaspergillic acid from dipeptidyl aldehydes》.HPLC of Formula: 87694-50-6 The article contains the following contents:

2(1H)-pyrazinone ring-containing natural products, flavacol, deoxymuta-aspergillic acid and optically active deoxyaspergillic acid, were easily synthesized by a newly developed procedure for preparation of 2(1H)-pyrazinone derivatives from dipeptidyl substrates BocNHCH(R2)CONHCH(R1)CON(Me)OMe (R1 = iso-Bu, iso-Pr, sec-Bu(S), sec-Bu(R); R2 = Bzl, iso-Bu). The absolute configuration of natural deoxyaspergillic acid was synthetically determined as S. After reading the article, we found that the author used (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.HPLC of Formula: 87694-50-6 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.

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

Mokotoff, Michael; Ren, Kaijun; Wong, Lan K.; LeFever, Ann V.; Lee, Ping C. published their research in Journal of Medicinal Chemistry on December 11 ,1992. The article was titled 《Synthesis and biological evaluation of novel potent antagonists of the bombesin/gastrin releasing peptide receptor》.Synthetic Route of C13H26N2O4 The article contains the following contents:

The solid-phase synthesis and antagonist activity of 20 C-terminal analogs of gastrin releasing peptide (GRP) are reported.. The ability of each analog to inhibit bombesin (BN)-stimulated amylase release from rat pancreatic acini was determined, and those showing antagonist activity were further evaluated for their ability to inhibit BN stimulated [3H]-thymidine uptake in serum-starved 3T3 cells. The assays also included two known peptide antagonists, ([Leu14,ψ13,14]BN) (I) and (N-pivaloyl-GRP20-25-(R)-2-methyl-4-nonylamide) (II), as pos. controls. On the basis of these assays we suggest that a des-Met27,Leu26-ψ[CH2NHCOCH3]GRP C-terminal octapeptide imparts antagonist activity. The two most active compounds are peptides [D-Phe19,Leu26-ψ(CH2NHCOCH3)]GRP19-26 (III) and [D-Phe19,Gln20,Leu26-ψ(CH2NHCOCH3)]GRP19-26 (IV). In their ability to inhibition BN stimulated [3H]-thymidine uptake, the IC50 of peptides I, II, III, and IV were 43, 31, 3, and 33 nM, resp. In conclusion, the novel C-terminal ψ[CH2NHCOCH3] bond promises to be a useful peptide backbone modification for imparting antagonism in GRP/BN analogs. The experimental part of the paper was very detailed, including the reaction process 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 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

Recommanded Product: (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamideOn June 1, 2014, Zhang, Jiankang; Cao, Jiayi; Xu, Lei; Zhou, Yubo; Liu, Tao; Li, Jia; Hu, Yongzhou published an article in Bioorganic & Medicinal Chemistry. The article was 《Design, synthesis and biological evaluation of novel tripeptidyl epoxyketone derivatives constructed from β-amino acid as proteasome inhibitors》. The article mentions the following:

A series of novel tripeptidyl epoxyketone derivatives constructed from β-amino acid were designed, synthesized and evaluated as proteasome inhibitors. All target compounds were tested for their proteasome inhibitory activities and selected compounds were tested for their anti-proliferation activities against two multiple myeloma (MM) cell lines RPMI 8226 and NCI-H929. Among them, eleven compounds exhibited proteasome inhibitory rates of more than 50% at the concentration of 1 μg/mL and nine compounds showed anti-proliferation activities with IC50 values at low micromolar level. Compound I displayed the most potent proteasome inhibitory activities (IC50 = 0.11 ± 0.01 μM) and anti-proliferation activities with IC50 = 0.23 ± 0.01 and 0.17 ± 0.02 μM against two tested cell lines. Addnl., the poly-ubiquitin accumulation in the western blot anal. supported that proteasome inhibition in a cellular system was induced by compound I. All these exptl. results confirmed that β-amino acid can be introduced as a building block for the development of proteasome inhibitors. The experimental process involved the reaction of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Recommanded Product: (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.Recommanded Product: (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide 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