Tag: 200-300

On March 8, 2018, Lopez-Tapia, Francisco; Brotherton-Pleiss, Christine; Yue, Peibin; Murakami, Heide; Costa Araujo, Ana Carolina; Reis dos Santos, Bruna; Ichinotsubo, Erin; Rabkin, Anna; Shah, Raj; Lantz, Megan; Chen, Suzie; Tius, Marcus A.; Turkson, James published an article.Synthetic Route of 98946-18-0 The title of the article was Linker variation and structure-activity relationship analysis of carboxylic acid-based small molecule STAT3 inhibitors. And the article contained the following:

The mol. determinants for the activities of the reported benzoic acid (SH4-54), salicylic acid (BP-1-102), and benzohydroxamic acid (SH5-07)-based STAT3 inhibitors were investigated to design optimized analogs. All three leads are based on an N-methylglycinamide scaffold, with its two amine groups condensed with three different functionalities. The three functionalities and the CH2 group of the glycinamide scaffold were sep. modified. The replacement of the pentafluorobenzene or cyclohexylbenzene, or replacing the benzene ring of the aromatic carboxylic or hydroxamic acid motif with heterocyclic components (containing nitrogen and oxygen elements) all decreased potency. Notably, the Ala-linker analogs, (I) (R1 = H and OH), and the Pro-based derivative (II) (X = CH2), all with (R)-configuration at the chiral center, had improved inhibitory activity and selectivity against STAT3 DNA-binding activity in vitro, with IC50 of 3.0 ± 0.9, 1.80 ± 0.94, and 2.4 ± 0.2 μM, resp. Compounds I and II and other analogs inhibited constitutive STAT3 phosphorylation and activation in human breast cancer and melanoma lines, and blocked tumor cell viability, growth, colony formation, and migration in vitro. Pro-based analog, II (X = O)(sodium salt), with a relatively polar tetrahydropyranyl (THP) ring, instead of the cyclohexyl, showed improved permeability. In general, the (R)-configuration Pro-based analogs showed the overall best profile, including physicochem. properties (e.g., microsomal metabolic stability, Caco-2 permeability), and in particular, II (X = CH2) showed improved tumor-cell specificity. The experimental process involved the reaction of tert-Butyl trichloroacetimidate(cas: 98946-18-0).Synthetic Route of 98946-18-0

The Article related to amino acid sulfonamide synthesis stat3 inhibitor structure activity pharmacokinetic, antitumor agent metabolic stability permeability stat3 dna binding inhibitor, alanine proline sulfonylation pentafluorobenzene cyclohexylbenzene acylation amination reductive alkylation, sulfonamide methylglycinamide drug design mechanism action and other aspects.Synthetic Route of 98946-18-0

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

On March 8, 2018, Lopez-Tapia, Francisco; Brotherton-Pleiss, Christine; Yue, Peibin; Murakami, Heide; Costa Araujo, Ana Carolina; Reis dos Santos, Bruna; Ichinotsubo, Erin; Rabkin, Anna; Shah, Raj; Lantz, Megan; Chen, Suzie; Tius, Marcus A.; Turkson, James published an article.Computed Properties of 99-60-5 The title of the article was Linker variation and structure-activity relationship analysis of carboxylic acid-based small molecule STAT3 inhibitors. And the article contained the following:

The mol. determinants for the activities of the reported benzoic acid (SH4-54), salicylic acid (BP-1-102), and benzohydroxamic acid (SH5-07)-based STAT3 inhibitors were investigated to design optimized analogs. All three leads are based on an N-methylglycinamide scaffold, with its two amine groups condensed with three different functionalities. The three functionalities and the CH2 group of the glycinamide scaffold were sep. modified. The replacement of the pentafluorobenzene or cyclohexylbenzene, or replacing the benzene ring of the aromatic carboxylic or hydroxamic acid motif with heterocyclic components (containing nitrogen and oxygen elements) all decreased potency. Notably, the Ala-linker analogs, (I) (R1 = H and OH), and the Pro-based derivative (II) (X = CH2), all with (R)-configuration at the chiral center, had improved inhibitory activity and selectivity against STAT3 DNA-binding activity in vitro, with IC50 of 3.0 ± 0.9, 1.80 ± 0.94, and 2.4 ± 0.2 μM, resp. Compounds I and II and other analogs inhibited constitutive STAT3 phosphorylation and activation in human breast cancer and melanoma lines, and blocked tumor cell viability, growth, colony formation, and migration in vitro. Pro-based analog, II (X = O)(sodium salt), with a relatively polar tetrahydropyranyl (THP) ring, instead of the cyclohexyl, showed improved permeability. In general, the (R)-configuration Pro-based analogs showed the overall best profile, including physicochem. properties (e.g., microsomal metabolic stability, Caco-2 permeability), and in particular, II (X = CH2) showed improved tumor-cell specificity. The experimental process involved the reaction of 2-Chloro-4-nitrobenzoic acid(cas: 99-60-5).Computed Properties of 99-60-5

The Article related to amino acid sulfonamide synthesis stat3 inhibitor structure activity pharmacokinetic, antitumor agent metabolic stability permeability stat3 dna binding inhibitor, alanine proline sulfonylation pentafluorobenzene cyclohexylbenzene acylation amination reductive alkylation, sulfonamide methylglycinamide drug design mechanism action and other aspects.Computed Properties of 99-60-5

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

On March 4, 2020, Kayser, Silke; Temperini, Piero; Poulie, Christian B. M.; Staudt, Markus; Nielsen, Birgitte; Pickering, Darryl S.; Bunch, Lennart published an article.Recommanded Product: tert-Butyl trichloroacetimidate The title of the article was A Diversity Oriented Synthesis Approach to New 2,3-trans-Substituted L-Proline Analogs as Potential Ligands for the Ionotropic Glutamate Receptors. And the article contained the following:

Discovery of chem. tools for the ionotropic glutamate receptors continues to be a challenging task. Herein we report a diversity-oriented approach to new 2,3-trans-L-proline analogs whereby we study how the spatial orientation of the distal carboxylate group influence on binding affinity and receptor class and subtype selectivity. In total 10 new analogs were synthesized and the 14 stereoisomers characterized in binding assays at native rat ionotropic glutamate receptors, and at cloned human homomeric kainic acid (KA) receptor subtypes GluK1-3. The study identified isoxazole analogs (I) (R1 = OH, CO2H), which displayed selectivity in binding at native N-methyl-D-aspartate (NMDA) receptors over native α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) and KA receptors, in the high nanomolar to low micromolar range. Furthermore, analogs (II) showed preference in binding affinity for GluK3 over GluK1,2. Finally, analog (III) displayed high nanomolar affinity for native NMDA receptors as well as for homomeric GluK3 receptors. The experimental process involved the reaction of tert-Butyl trichloroacetimidate(cas: 98946-18-0).Recommanded Product: tert-Butyl trichloroacetimidate

The Article related to proline analog enantioselective diastereoselective synthesis ka nmda ampa ligand, ka nmda ampa ionotropic glutamate receptor binding structure activity, aryl proline trans cis epimerization coupling aminoquinoline alkynylation protection, diversity-oriented synthesis, ionotropic glutamate receptors, proline analogs, sar study and other aspects.Recommanded Product: tert-Butyl trichloroacetimidate

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

On February 1, 2020, Pedatella, Silvana; Cerchia, Carmen; Manfra, Michele; Cioce, Anna; Bolognese, Adele; Lavecchia, Antonio published an article.Reference of tert-Butyl trichloroacetimidate The title of the article was Antitumor agents 7. Synthesis, antiproliferative activity and molecular modeling of new L-lysine-conjugated pyridophenoxazinones as potent DNA-binding ligands and topoisomerase IIα inhibitors. And the article contained the following:

A series of L-lysine-conjugated pyridophenoxazinones (I), (II), (III) and (IV) were designed and synthesized for developing compounds with multimodal anticancer potentialities. All compounds inhibited the proliferation of a panel of human liquid and solid neoplastic cell lines. Compounds I (X = N, Y = CH) and IV (X = N, Y = CH) were the most active compounds with IC50 values in the submicromolar range. UV-vis, 1H NMR, unwinding, and docking experiments demonstrated that they intercalate between the middle 5′-GC-3′ base pairs with the carboxamide side chain lying into major groove. Charge-transfer contribution to the complex stability, evaluated by ab initio calculations, was found to correlate with cytotoxicity. Relaxation and cleavage assays showed that I (X = N, Y = CH) and IV (X = N, Y = CH) selectively target Topo IIα over Topo IIβ and stimulate the formation of covalent Topo II-DNA complexes, functioning as poisons. Moreover, compound IV (X = N, Y = CH) induced DNA damage and arrested MCF-7 cells at the G2/M phase. Altogether, the work provides interesting structure-activity relationships in the pyridophenoxazinone-L-lysine conjugate series and identifies IV (X = N, Y = CH) as a promising candidate for further in vivo evaluation. The experimental process involved the reaction of tert-Butyl trichloroacetimidate(cas: 98946-18-0).Reference of tert-Butyl trichloroacetimidate

The Article related to lysine pyridophenoxazinone synthesis antitumor agent dna damage topoisomerase inhibiting, structure activity antitumor dna binding enzyme inhibiting mol docking, dna lysine pyridophenoxazinone complex, mol structure lysine pyridophenoxazinone hydrogen bond qm ab initio, antiproliferative activity, dna damage, docking studies and other aspects.Reference of tert-Butyl trichloroacetimidate

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

On November 1, 2021, Ishida, Hiroyuki published an article.Electric Literature of 99-60-5 The title of the article was Role of pKa in establishing crystal structures of six hydrogen-bonded compounds of with different isomers of chloro- and nitro-substituted benzoic acids. And the article contained the following:

The structures of the six hydrogen-bonded 1:1 compounds of 4-methylquinoline (C10H9N) with chloro- and nitro-substituted benzoic acids (C7H4ClNO4), namely, 4-methylquinolinium 2-chloro-4-nitrobenzoate, C10H10N+·C7H3ClNO4-, (I), 4-methylquinoline-2-chloro-5-nitrobenzoic acid (1/1), C10H9N·C7H4ClNO4, and (II), 4-methylquinolinium 2-chloro-6-nitrobenzoate, C10H9.63N0.63+·C7H3.37ClNO40.63-. The (III), 4-methylquinolinium 3-chloro-2-nitrobenzoate, C10H9.54N0.54+·C7H3.46ClNO40.54-, (IV), 4-methylquinolinium 4-chloro-2-nitrobenzoate, C10H10N+·C7H3ClNO4-, (V), and 4-methylquinolinium 5-chloro-2-nitrobenzoate, C10H10N+·C7H3ClNO4-, have been determined at 185-190 K. In each compound, the acid and base mols. are linked by a short hydrogen bond between a carboxy (or carboxylate) O atom and an N atom of the base. The O···N distances are 2.5652 (14), 2.556 (3), 2.5485 (13), 2.5364 (13), 2.5568 (13) and 2.5252 (11) Å, resp., for compounds (I)-(VI). In the hydrogen-bonded acid-base units of (III) and (IV), the H atoms are each disordered over two positions with O site:N site occupancies of 0.37 (3):0.63 (3) and 0.46 (3):0.54 (4), resp., for (III) and (IV). The H atoms in the hydrogen-bonded units of (I), (V) and (VI) are located at the N-atom site, while the H atom in (II) is located at the O-atom site. In all the crystals of (I)-(VI), π-π stacking interactions between the quinoline ring systems and C-H···O hydrogen bonds are observed Similar layer structures are constructed in (IV)-(VI) through these interactions together with π-π interactions between the benzene rings of the adjacent acid mols. A short Cl···Cl contact and an N-O···π interaction are present in (I), while a C-H···Cl hydrogen bond and a π-π interaction between the benzene ring of the acid mol. and the quinoline ring system in (II), and a C-H···π interaction in (III) are observed Hirshfeld surfaces for the title compounds mapped over dnorm and shape index were generated to visualize the weak intermol. interactions. The experimental process involved the reaction of 2-Chloro-4-nitrobenzoic acid(cas: 99-60-5).Electric Literature of 99-60-5

The Article related to methylquinoline benzoic acid crystal structure isomer, 2-chloro-4-nitro­benzoic acid, 2-chloro-5-nitro­benzoic acid, 2-chloro-6-nitro­benzoic acid, 3-chloro-2-nitro­benzoic acid, 4-chloro-2-nitro­benzoic acid, 4-methyl­quinoline, 5-chloro-2-nitro­benzoic acid, hirshfeld surface, crystal structure, disorder, hydrogen bond and other aspects.Electric Literature of 99-60-5

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

On September 3, 2021, Pollack, Scott R.; Dion, Amelie published an article.HPLC of Formula: 14602-86-9 The title of the article was Metal-free stereoselective synthesis of (E)- and (Z)-N-monosubstituted β-aminoacrylates via condensation reactions of carbamates. And the article contained the following:

Two efficient, stereoselective methods for the preparation of (E)- or (Z)-β-aminoacrylates via acid- or base-promoted condensation reactions of carbamates are described. The base-promoted reaction is E-selective, while acid catalysis can, through the choice of solvent, selectively form E or Z. The acid-catalyzed E-selective process proceeds through a crystallization obviating the need for chromatog. purification The experimental process involved the reaction of (1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl carbonochloridate(cas: 14602-86-9).HPLC of Formula: 14602-86-9

The Article related to carbamate alkoxyacrylate acid catalyst metal free diastereoselective condensation reaction, dialkoxypropanoate carbamate acid catalyst metal free diastereoselective condensation reaction, propynoate carbamate base catalyst diastereoselective condensation reaction, aminoacrylate preparation stereoselective metal free and other aspects.HPLC of Formula: 14602-86-9

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Schwenk, R.; Togni, A. published an article in 2015, the title of the article was P-Trifluoromethyl ligands derived from Josiphos in the Ir-catalysed hydrogenation of 3,4-dihydroisoquinoline hydrochlorides.Reference of (1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl carbonochloridate And the article contains the following content:

The synthesis of mono P-trifluoromethyl and therefore P-stereogenic Xyliphos-derived ligands CpFeC5H3(PPhCF3)(CMeHP(xyl)2) (5, xyl = C6H3Me2-3,5) and their application in the Ir-catalyzed enantioselective hydrogenation of 1-substituted 3,4-dihydroisoquinolinium species (DHIQ) are reported. The ligands were prepared following previous procedures involving the reaction of a bis(trifluoromethyl)phosphine with lithiated (R)-Ugi amine (R)-CpFeC5H3Li(CHMeNMe2) (1). Chloroiridium(I) cyclooctadiene precatalysts containing these new partially electron-poor ligands are poorly active in the hydrogenation of free 1-phenyl-3,4-dihydroisoquinoline (12a). However, the corresponding hydrochloride 12a·HCl was smoothly reduced at 55-60° and 100 bar H pressure. The (SP)-configured ligand (SP)-5 yielded significantly higher enantioselectivity in hydrogenation experiments than its P-stereoisomeric counterpart (RP)-5. These new ligands were subsequently applied in the hydrogenation of twelve different 1-substituted 3,4-DHIQ chlorides. Good to excellent enantioselectivity was observed for substrates bearing relatively large substituents in position 1, reaching 96% ee for 1-Ph-DHIQ chloride 12a·HCl without the help of any additives. Furthermore, an interesting counterion effect was found with chloride being the best and hexafluorophosphate being very detrimental to enantioselectivity. The experimental process involved the reaction of (1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl carbonochloridate(cas: 14602-86-9).Reference of (1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl carbonochloridate

The Article related to xyliphos fluoromethyl iridium catalyst preparation hydrogenation enantioselective dihydroisoquinoline hydrochloride, fluoromethyl phosphinylferrocenyl iridium preparation hydrogenation catalyst enantioselective hydroisoquinoline hydrochloride, crystal mol structure fluoromethyl xyliphos platinum iridium preparation and other aspects.Reference of (1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl carbonochloridate

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Xu, Youwen; Cankaya, Aylin Sibel; Hoque, Ruma; Lee, So Jeong; Shea, Colleen; Kersting, Lena; Schueller, Michael; Fowler, Joanna S.; Szalda, David; Alexoff, David; Riehl, Barbara; Gleede, Tassilo; Ferrieri, Richard A.; Qu, Wenchao published an article in 2018, the title of the article was Synthesis of L-[4-11C]asparagine by ring-opening nucleophilic 11C-cyanation reaction of a chiral cyclic sulfamidate precursor.Safety of tert-Butyl trichloroacetimidate And the article contains the following content:

The development of a convenient and rapid method to synthesize radiolabeled, enantiomerically pure amino acids (AAs) as potential positron emission tomog. (PET) imaging agents for mapping various biochem. transformations in living organisms remains a challenge. This is especially true for the synthesis of carbon-11-labeled AAs given the short half-life of carbon-11 (11C, t1/2=20.4 min). A facile synthetic pathway to prepare enantiomerically pure 11C-labeled L-asparagine was developed using a partially protected serine as a starting material with a four-step transformation providing a chiral five-membered cyclic sulfamidate as the radiolabeling precursor. Its structure and absolute configuration were confirmed by X-ray crystallog. Utilizing a [11C]cyanide nucleophilic ring opening reaction followed by selective acidic hydrolysis and deprotection, enantiomerically pure L-[4-11C]asparagine was synthesized. Further optimization of reaction parameters, including base, metal ion source, solvent, acid component, reaction temperature and reaction time, a reliable two-step method for synthesizing L-[4-11C]asparagine was presented: within a 45±3 min (n = 5, from end-of-bombardment), the desired enantiomerically pure product was synthesized with the initial nucleophilic cyanation yield of 69±4 % (n = 5) and overall two-step radiochem. yield of 53±2 % (n = 5) based on starting [11C]HCN, and with radiochem. purity of 96±2 % (n = 5). The experimental process involved the reaction of tert-Butyl trichloroacetimidate(cas: 98946-18-0).Safety of tert-Butyl trichloroacetimidate

The Article related to asparagine 11c labeled enantioselective total radiosynthesis pet imaging agent, chiral cyclic sulfamidate precursor ring opening nucleophilic cyanation hydrolysis, amino acid crystal structure, racemization cyanation kinetics reaction mechanism, amino acids, nucleophilic, radiochemistry, ring opening, sulfamidate and other aspects.Safety of tert-Butyl trichloroacetimidate

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Albrecht, Dominik; Vogt, Florian; Bach, Thorsten published an article in 2010, the title of the article was Diastereo- and Enantioselective Intramolecular [2+2] Photocycloaddition Reactions of 3-(ω’-Alkenyl)- and 3-(ω’-Alkenyloxy)-Substituted 5,6-Dihydro-1H-pyridin-2-ones.Electric Literature of 14602-86-9 And the article contains the following content:

3-(ω’-Alkenyl)-substituted 5,6-dihydro-1H-pyridin-2-ones I (n = 1-3) were prepared as photocycloaddition precursors either by cross-coupling from 3-iodo-5,6-dihydro-1H-pyridin-2-one or, more favorably, from the corresponding α-(ω’-alkenyl)-substituted δ-valerolactams by a selenylation/elimination sequence (56-62% overall yield). 3-(ω’-Alkenyloxy)-substituted 5,6-dihydro-1H-pyridin-2-ones II (n = 1, 2) were accessible in 43 and 37% overall yield from 3-diazopiperidin-2-one by an α,α-chloroselenylation reaction at the 3-position followed by nucleophilic displacement of a chloride ion with an ω-alkenolate and oxidative elimination of selenoxide. Upon irradiation at λ = 254 nm, the precursor compounds underwent a clean intramol. [2+2] photocycloaddition reaction. The substrates tethered by a two-atom chain exclusively delivered the resp. crossed products III (X = CH2, O), and the substrates tethered by longer chains, gave the straight products IV (n = 1, X = CH2, O; n = 2, X = CH2). The completely regio- and diastereoselective photocycloaddition reactions proceeded in 63-83% yield. Irradiation in the presence of the chiral templates (-)-V and (+)-VI at -75° in toluene rendered the reactions enantioselective with selectivities varying between 40 and 85% ee. Truncated template rac-VI was prepared as a noranalogue of the well-established template V in eight steps and 56% yield from the Kemp triacid. Subsequent resolution delivered the enantiomerically pure templates (-)-ent-VI and (+)-VI. The outcome of the reactions is compared to the results achieved with 4-substituted 5,6-dihydro-1H-pyridin-2-ones and quinolones. The experimental process involved the reaction of (1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl carbonochloridate(cas: 14602-86-9).Electric Literature of 14602-86-9

The Article related to alkenyl substituted valerolactam selenylation elimination, dihydropyridinone alkenyl substituted derivative preparation photocycloaddition, piperidinone tricyclic derivative stereoselective preparation chiral complexing reagent, kemp triacid tetrahydroaminonaphthol chiral template preparation resolution and other aspects.Electric Literature of 14602-86-9

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

On December 31, 2019, He, Zhi-Tao; Hartwig, John F. published an article.Related Products of 98946-18-0 The title of the article was Palladium-catalyzed α-arylation for the addition of small rings to aromatic compounds. And the article contained the following:

A generally applicable approach to attach small rings to a wide range of aromatic compounds by palladium-catalyzed α-arylation of cyclopropyl, cyclobutyl and azetidinyl esters was reported. The direct α-arylation of cyclopropyl esters and cyclobutyl esters was achieved in high yield by ensuring that rate of coupling exceeded rate of Claisen condensation. The α-arylation of azetidines was achieved without ring opening of strained saturated heterocycle by conducting reactions with an azetidine derivative bearing a benzyl protecting group on nitrogen. Mechanistic studies showed that α-arylation of small rings was challenging because of the weak acidity of α C-H bond (cyclopropanes), strong sensitivity of strained esters to Claisen condensation (cyclobutatanes), or facile decomposition of enolates (azetidinyl esters). The experimental process involved the reaction of tert-Butyl trichloroacetimidate(cas: 98946-18-0).Related Products of 98946-18-0

The Article related to aryl cyclobutyl ester preparation, cyclobutyl ester aryl bromide alpha arylation palladium catalyst, azetidinyl ester aryl preparation, azetidine ester aryl bromide alpha arylation palladium catalyst, cyclopropyl ester aryl preparation, bromoarene cyclopropyl ester alpha arylation palladium catalyst and other aspects.Related Products of 98946-18-0

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics