Tag: 100-200

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

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 《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

Safety of N-(Pyridin-4-yl)isonicotinamideOn March 5, 2015, O’Donovan, Megan E.; LaDuca, Robert L. published an article in Journal of Molecular Structure. The article was 《Zinc coordination polymers containing substituted isophthalate ligands and fragments from in situ hydrolysis of 4-pyridylisonicotinamide》. The article mentions the following:

Hydrothermal treatment of Zn nitrate, a 5-substituted isophthalic acid, and 4-pyridylisonicotinamide (4-pina) resulted in crystalline coordination polymers that incorporated different fragments formed by in situ hydrolysis of the 4-pina precursor. These materials were characterized by single crystal x-ray diffraction. In the case of {[4-ampyrH]2[Zn(hip)2]·H2O}n (1, 4-ampyrH = 4-aminopyridinium, hip = 5-hydroxyisophthalate), anionic [Zn(hip)2]n2n- (4,4) grid layers co-crystallize with protonated 4-ampyr cations. Using 5-nitroisophthalic acid (H2nip), [Zn7(isonic)4(OH)6(nip)2]n (2, isonic = isonicotinate) was formed. This material manifests [Zn7(OH)6]n cationic inorganic chain motifs linked by isonic and nip ligands into a noninterpenetrated 3-dimensional coordination polymer network with pcu topol. Luminescent behavior is attributed to intra-ligand MO transitions. The results came from multiple reactions, including the reaction of N-(Pyridin-4-yl)isonicotinamide(cas: 64479-78-3Safety of N-(Pyridin-4-yl)isonicotinamide)

N-(Pyridin-4-yl)isonicotinamide(cas: 64479-78-3) belongs to amides.Safety of N-(Pyridin-4-yl)isonicotinamideAmides 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

《Efficient Copper(II)-Catalyzed Transamidation of Nonactivated Primary Carboxamides and Ureas with Amines》 was written by Zhang, Min; Imm, Sebastian; Baehn, Sebastian; Neubert, Lorenz; Neumann, Helfried; Beller, Matthias. Synthetic Route of C8H9NO2 And the article was included in Angewandte Chemie, International Edition in 2012. The article conveys some information:

A copper(II) catalyzed transamidation process using nonactivated primary carboxamides and ureas with amines is presented. For this technique, the Cu(OAc)2 is fairly inexpensive and convenient to use without special precautions. Fortunately, a wide range of amides, ureas, chiral amines can be synthesized from primary carboxamides and amines in good to excellent yields. By extension this protocol can be applied to the synthesis of amides, peptide, polyamides and heterocycles. In the part of experimental materials, we found many familiar compounds, such as 2-Hydroxy-N-phenylacetamide(cas: 4746-61-6Synthetic Route of C8H9NO2)

2-Hydroxy-N-phenylacetamide(cas: 4746-61-6) 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. Synthetic Route of C8H9NO2

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

Synthetic Route of C4H9NO2In 2020 ,《Antibacterial Spiropyrimidinetriones with N-Linked Azole Substituents on a Benzisoxazole Scaffold Targeting DNA Gyrase》 was published in Journal of Medicinal Chemistry. The article was written by Basarab, Gregory S.; Doig, Peter; Eyermann, Charles J.; Galullo, Vincent; Kern, Gunther; Kimzey, Amy; Kutschke, Amy; Morningstar, Marshall; Schuck, Virna; Vishwanathan, Karthick; Zhou, Fei; Gowravaram, Madhusudhan; Hauck, Sheila. The article contains the following contents:

Herein, we report spiropyrimidinetriones (SPTs) incorporating N-linked azole substituents on a benzisoxazole scaffold with improved Gram-pos. antibacterial activity relative to previously described analogs. SPTs have an unusual spirocyclic architecture and represent a new antibacterial class of bacterial DNA gyrase and topoisomerase IV inhibitors. They are not cross-resistant to fluoroquinolones and other DNA gyrase/topoisomerase IV inhibitors used clin. The activity of the SPTs was assessed for DNA gyrase inhibition, and the antibacterial activity across Gram-pos. and Gram-neg. pathogens with N-linked 1,2,4-triazoles substituted on the 5-position provides the most worthwhile profile. Directed nucleophilic and electrophilic chem. was developed to vary this 5-position with carbon, nitrogen, or oxygen substituents and explore structure-activity relationships including those around a target binding model. Compounds with favorable pharmacokinetic parameters were identified, and two compounds demonstrated cidality in a mouse model of Staphylococcus aureus infection. After reading the article, we found that the author used N-Methoxy-N-methylacetamide(cas: 78191-00-1Synthetic Route of C4H9NO2)

N-Methoxy-N-methylacetamide(cas: 78191-00-1) 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).Synthetic Route of C4H9NO2

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

In 2022,Khiar-Fernandez, Nora; Zian, Debora; Vazquez-Villa, Henar; Martinez, R. Fernando; Escobar-Pena, Andrea; Foronda-Sainz, Roman; Ray, Manisha; Puigdomenech-Poch, Maria; Cincilla, Giovanni; Sanchez-Martinez, Melchor; Kihara, Yasuyuki; Chun, Jerold; Lopez-Vales, Ruben; Lopez-Rodriguez, Maria L.; Ortega-Gutierrez, Silvia published an article in Journal of Medicinal Chemistry. The title of the article was 《Novel Antagonist of the Type 2 Lysophosphatidic Acid Receptor (LPA2), UCM-14216, Ameliorates Spinal Cord Injury in Mice》.Product Details of 683-57-8 The author mentioned the following in the article:

Spinal cord injuries (SCIs) irreversibly disrupt spinal connectivity, leading to permanent neurol. disabilities. Current medical treatments for reducing the secondary damage that follows the initial injury are limited to surgical decompression and anti-inflammatory drugs, so there is a pressing need for new therapeutic strategies. Inhibition of the type 2 lysophosphatidic acid receptor (LPA2) has recently emerged as a new potential pharmacol. approach to decrease SCI-associated damage. Toward validating this receptor as a target in SCI, we have developed a new series of LPA2 antagonists, among which compound 54 (UCM-14216) stands out as a potent and selective LPA2 receptor antagonist (Emax = 90%, IC50 = 1.9 μM, KD = 1.3 nM; inactive at LPA1,3-6 receptors). This compound shows efficacy in an in vivo mouse model of SCI in an LPA2-dependent manner, confirming the potential of LPA2 inhibition for providing a new alternative for treating SCI.2-Bromoacetamide(cas: 683-57-8Product Details of 683-57-8) 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.Product Details of 683-57-8

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

In 2022,Yan, Yu-Hang; Li, Wenfang; Chen, Wei; Li, Chao; Zhu, Kai-Rong; Deng, Ji; Dai, Qing-Qing; Yang, Ling-Ling; Wang, Zhenling; Li, Guo-Bo published an article in European Journal of Medicinal Chemistry. The title of the article was 《Structure-guided optimization of 1H-imidazole-2-carboxylic acid derivatives affording potent VIM-Type metallo-β-lactamase inhibitors》.Product Details of 683-57-8 The author mentioned the following in the article:

X-ray structure-guided optimization of 1H-imidazole-2-carboxylic acid (ICA) derivatives, I [R1 = cyclopropyl, 4-pyridylmethyl, 2-(1-methyltetrazol-5-yl)sulfanylethyl, etc.; R2 = R3 = Me, cyclopropyl, Ph, etc.] was reported by considering how to engage with the active-site flexible loops and improve penetration into Gram-neg. bacteria. Structure-activity relationship studies revealed the importance of appropriate substituents at ICA 1-position to achieve potent inhibition to class B1 MBLs, particularly the Verona Integron-encoded MBLs (VIMs), mainly by involving ingenious interactions with the flexible active site loops as observed by crystallog. analyses. Of the tested ICA inhibitors, I [R1 = 4-pyridylmethyl, R2 = R3 = H] displayed potent synergistic antibacterial activity with meropenem against engineered Escherichia coli strains and even intractable clin. isolated Pseudomonas aeruginosa producing VIM-2 MBL. The morphol. and internal structural changes of bacterial cells after treatment further demonstrated that I [R1 = 4-pyridylmethyl, R2 = R3 = H] crossed the outer membrane and reversed the activity of meropenem. Moreover, I [R1 = 4-pyridylmethyl, R2 = R3 = H] showed good pharmacokinetic and safety profile in vivo, which could be a potential candidate for combating VIM-mediated Gram-neg. carbapenem resistance. The results came from multiple reactions, including the reaction of 2-Bromoacetamide(cas: 683-57-8Product Details of 683-57-8)

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.Product Details of 683-57-8

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

Gopalsamy, Ariamala; Aulabaugh, Ann E.; Barakat, Amey; Beaumont, Kevin C.; Cabral, Shawn; Canterbury, Daniel P.; Casimiro-Garcia, Agustin; Chang, Jeanne S.; Chen, Ming Z.; Choi, Chulho; Dow, Robert L.; Fadeyi, Olugbeminiyi O.; Feng, Xidong; France, Scott P.; Howard, Roger M.; Janz, Jay M.; Jasti, Jayasankar; Jasuja, Reema; Jones, Lyn H.; King-Ahmad, Amanda; Knee, Kelly M.; Kohrt, Jeffrey T.; Limberakis, Chris; Liras, Spiros; Martinez, Carlos A.; McClure, Kim F.; Narayanan, Arjun; Narula, Jatin; Novak, Jonathan J.; O’Connell, Thomas N.; Parikh, Mihir D.; Piotrowski, David W.; Plotnikova, Olga; Robinson, Ralph P.; Sahasrabudhe, Parag V.; Sharma, Raman; Thuma, Benjamin A.; Vasa, Dipy; Wei, Liuqing; Wenzel, A. Zane; Withka, Jane M.; Xiao, Jun; Yayla, Hatice G. published an article in 2021. The article was titled 《PF-07059013: A Noncovalent Modulator of Hemoglobin for Treatment of Sickle Cell Disease》, and you may find the article in Journal of Medicinal Chemistry.Reference of N-Methoxy-N-methylacetamide The information in the text is summarized as follows:

Sickle cell disease (SCD) is a genetic disorder caused by a single point mutation (β6 Glu → Val) on the β-chain of adult Hb (HbA) that results in sickled Hb (HbS). In the deoxygenated state, polymerization of HbS leads to sickling of red blood cells (RBC). Several downstream consequences of polymerization and RBC sickling include vaso-occlusion, hemolytic anemia, and stroke. We report the design of a noncovalent modulator of HbS, clin. candidate PF-07059013 (23). The seminal hit mol. was discovered by virtual screening and confirmed through a series of biochem. and biophys. studies. After a significant optimization effort, we arrived at 23, a compound that specifically binds to Hb with nanomolar affinity and displays strong partitioning into RBCs. In a 2-wk multiple dose study using Townes SCD mice, 23 showed a 37.8% (±9.0%) reduction in sickling compared to vehicle treated mice. 23 (PF-07059013) has advanced to phase 1 clin. trials. The experimental part of the paper was very detailed, including the reaction process of N-Methoxy-N-methylacetamide(cas: 78191-00-1Reference of N-Methoxy-N-methylacetamide)

N-Methoxy-N-methylacetamide(cas: 78191-00-1) 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).Reference of N-Methoxy-N-methylacetamide

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

The author of 《Direct Phenolysis Reactions of Unactivated Amides into Phenolic Esters Promoted by a Heterogeneous CeO2 Catalyst》 were Rashed, Nurnobi Md.; Siddiki, S. M. A. Hakim; Touchy, Abeda Sultana; Jamil, A. R. Md.; Poly, Sharmin Sultana; Toyao, Takashi; Maeno, Zen; Shimizu, Ken-ichi. And the article was published in Chemistry – A European Journal in 2019. Recommanded Product: 78191-00-1 The author mentioned the following in the article:

The direct catalytic esterification of amides that leads to the construction of C-O bonds through the cleavage of amide C-N bonds is a highly attractive strategy in organic synthesis. While aliphatic and aromatic alcs. can be readily used for the alcoholysis of activated and unactivated amides, the introduction of phenols is more challenging due to their lower nucleophilicity in the phenolysis of unactivated amides. Herein, phenols can be used for the phenolysis of unactivated amides into the corresponding phenolic esters using a simple heterogenous catalytic system based on CeO2 under additive-free reaction conditions was demonstrated. The method tolerates a broad variety of functional groups (>50 examples) in the substrates. Results of kinetic studies afforded mechanistic insights into the principles governing this reaction, suggesting that the cooperative effects of the acid-base functions of catalysts would be of paramount importance for the efficient progression of the C-N bond breaking process, and consequently, CeO2 showed the best catalytic performance among the catalysts explored. In the part of experimental materials, we found many familiar compounds, such as N-Methoxy-N-methylacetamide(cas: 78191-00-1Recommanded Product: 78191-00-1)

N-Methoxy-N-methylacetamide(cas: 78191-00-1) belongs to anime.Typically the presence of an amine functional group is deduced by a combination of techniques, including mass spectrometry as well as NMR and IR spectroscopies. 1H NMR signals for amines disappear upon treatment of the sample with D2O. In their infrared spectrum primary amines exhibit two N-H bands, whereas secondary amines exhibit only one.Recommanded Product: 78191-00-1

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