Month: October 2022

Wang, Zhi-Xian; Duan, Weili; Wiebe, Leonard I.; Balzarini, Jan; De Clercq, Erik; Knaus, Edward E. published the artcile< Synthesis of 1-(2-deoxy-β-D-ribofuranosyl)-2,4-difluoro-5-substituted-benzene thymidine mimics, some related α-anomers, and their evaluation as antiviral and anticancer agents>, Product Details of C6H3F2I, the main research area is nucleoside deoxyribofuranosyldifluorobenzene thymidine mimic synthesis antiviral cytotoxicity anticancer.

A group of unnatural 1-(2-deoxy-β-D-ribofuranosyl)-2,4-difluorobenzenes having a variety of C-5 substituents (H, Me, F, Cl, Br, I, CF3, CN, NO2, NH2), designed as thymidine mimics, were synthesized for evaluation as anticancer and antiviral agents. The coupling reaction of 3,5-bis-O-(p-chlorobenzoyl)-2-deoxy-α-D-ribofuranosyl chloride with an organocadmium reagent [(2,4-difluorophenyl)2Cd] afforded a mixture of the α- and β-anomeric products (α:β = 3:1 to 10:1 ratio). Treatment of the α-anomer with BF3·Et2O in nitroethane at 110-120°C for 30 min was developed as an efficient method for epimerization of the major α-anomer to the desired β-anomer. The 5-substituted (H, Me, Cl, I, NH2) β-anomers exhibited negligible cytotoxicity in a MTT assay (CC50 = 10-3-10-4 M range), relative to thymidine (CC50 = 10-3-10-5 M range), against a variety of cancer cell lines. In contrast, the 5-NO2 derivative was more cytotoxic (CC50 = 10-5-10-6 M range). A number of 5-substituted β-anomers, and some related α-anomers, that were evaluated using a wide variety of antiviral assay systems [HSV-1, HSV-2, varicella-zoster virus (VZV), vaccinia virus, vesicular stomatitis, cytomegalovirus (CMV) and human immunodeficiency (HIV-1, HIV-2) viruses], showed that this class of unnatural C-aryl nucleoside mimics are inactive antiviral agents.

Nucleosides, Nucleotides & Nucleic Acids published new progress about Antitumor agents. 2265-92-1 belongs to class iodides-buliding-blocks, and the molecular formula is C6H3F2I, Product Details of C6H3F2I.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Kervefors, Gabriella; Kersting, Leonard; Olofsson, Berit published the artcile< Transition metal-free N-arylation of amino acid esters with diaryliodonium salts>, Formula: C7H3FIN, the main research area is arylated amino acid ester synthesis transition metal free; amino acid ester arylation diaryliodonium salt hypervalent reagent; arylation reaction mechanism solvent effect protective group; amino acids; arylation; diaryliodonium salts; hypervalent compounds; transition metal-free.

A transition metal-free approach for the N-arylation of amino acid derivatives has been developed. Key to this method is the use of unsym. diaryliodonium salts with anisyl ligands, which proved important to obtain high chemoselectivity and yields. The scope includes the transfer of both electron deficient, electron rich and sterically hindered aryl groups with a variety of different functional groups. Furthermore, a cyclic diaryliodonium salt was successfully employed in the arylation. The N-arylated products were obtained with retained enantiomeric excess.

Chemistry – A European Journal published new progress about Amino acid esters Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 887266-99-1 belongs to class iodides-buliding-blocks, and the molecular formula is C7H3FIN, Formula: C7H3FIN.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Yang, Peng-Fei; Shu, Wei published the artcile< Orthogonal Access to α-/β-Branched/Linear Aliphatic Amines by Catalyst-Tuned Regiodivergent Hydroalkylations>, Name: tert-Butyl (3-iodopropyl)carbamate, the main research area is amine preparation regioselective; chiral amine preparation regioselective enantioselective; alkenyl amine alkyl halide hydroalkylation metal catalyst; Amines; Chain Walking; Cobalt Catalysis; Hydroalkylations; Regiodivergent Reactions.

Herein, a catalyst-controlled synthesis of α-branched e.g., N-(1-phenylpentan-3-yl)benzamide, β-branched e.g., N-(2-methyl-4-phenylbutyl)benzamide and linear aliphatic amines e.g., N-(5-phenylpentyl)benzamide from Ni/Co-catalyzed regio- and site-selective hydroalkylations of alkenyl amines e.g., N-(prop-2-en-1-yl)benzamide with alkyl halides RX (R = butan-2-yl, Bn, 2-phenylethyl, 2-(1,3-dioxolan-2-yl)ethyl, etc.; X = I, Br) is developed. This catalytic protocol features the reliable prediction and control of the coupling position of alkylation to provide orthogonal access to α-branched, β-branched and linear alkyl amines from identical starting materials. This platform unlocks orthogonal reactivity and selectivity of nickel hydride and cobalt hydride chem. to catalytically repurpose three types of alkyl amines under mild conditions.

Angewandte Chemie, International Edition published new progress about Aliphatic amines Role: SPN (Synthetic Preparation), PREP (Preparation). 167479-01-8 belongs to class iodides-buliding-blocks, and the molecular formula is C8H16INO2, Name: tert-Butyl (3-iodopropyl)carbamate.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

D’Auria, Maurizio; De Mico, Antonella; D’Onofrio, Franco; Mendola, Daniele; Piancatelli, Giovanni published the artcile< Photochemical behavior of halothiophenes: synthesis of 5-arylthiophene-2-carboxylic esters>, Name: Methyl 5-iodothiophene-2-carboxylate, the main research area is photolysis halothiophene derivative reactivity mechanism; bithiophenecarboxylic acid propynyl; arylation photochem halothiophene derivative.

The arylation of 5-halothiophene-2-carbonitrile and Me 5-halothiophene-2-carboxylate by a photochem. process was investigated. Whereas 5-bromothiophene-2-carbonitrile is completely unreactive, the corresponding iodo derivative furnishes the dehalogenation product. In contrast, Me 5-iodothiophene-2-carboxylate gives the corresponding aryl and heteroaryl derivatives in good yields on irradiation in the presence of various aromatic substrates (benzene, p-xylene, naphthalene, thiophene, 2-bromothiophene and 2-chlorothiophene). The different reactivities of these compounds are explained. An application of this conversion to the synthesis of 5′-(1-propynyl)-2,2′-bithiophene-5-carboxylic acid is reported.

Journal of Photochemistry and Photobiology, A: Chemistry published new progress about Phosphorescence. 88105-22-0 belongs to class iodides-buliding-blocks, and the molecular formula is C6H5IO2S, Name: Methyl 5-iodothiophene-2-carboxylate.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Muthukaman, Nagarajan; Deshmukh, Sanjay; Tondlekar, Shital; Tambe, Macchindra; Pisal, Dnyandeo; Sarode, Neelam; Mhatre, Siddharth; Chakraborti, Samitabh; Shah, Daisy; Bhosale, Vikram M.; Kulkarni, Abhay; Mahat, Mahamad Yunnus A.; Jadhav, Satyawan B.; Gudi, Girish S.; Khairatkar-Joshi, Neelima; Gharat, Laxmikant A. published the artcile< Discovery of 5-(2-chloro-4'-(1H-imidazol-1-yl)-[1,1'-biphenyl]-4-yl)-1H-tetrazole as potent and orally efficacious S-nitrosoglutathione reductase (GSNOR) inhibitors for the potential treatment of COPD>, HPLC of Formula: 887266-99-1, the main research area is imidazolyl biaryl carboxylic acid preparation nitrosoglutathione reductase inhibition SAR; biaryl imidazolyl tetrazole preparation nitrosoglutathione reductase inhibition SAR; Bioavailability; Bronchodilation; Cigarette smoke (CS); GSNOR inhibitor; Glutathione (GSH); Reductase; S-nitrosoglutathione (GSNO).

Design, synthesis and structure-activity relationships (SAR) of novel imidazole-biaryl-tetrazole I [X = C, N; R1 = H, Me, F, Cl, CF3; R2 = H, Me, Et, Cl, cyclopropyl; R3 = H, Me] based GSNOR inhibitors were described. Many potent inhibitor compounds I [X = C, R1 = Cl, R2 = R3 = H; X = C, R1 = R3 = H, R2 = Me, Et; X = C, R1 = Cl, R2 = Me, R3 = H; X = C, R1 = F, R2 = Et, R3 = H; X = N, R1 = F, R2 = Me, R3 = H] and II [X = C, R1 = H, R2 = Me] were identified with low nanomolar activity (IC50s: <15 nM) along with adequate metabolic stability. Lead compounds I [X = C, R1 = Cl, R2 = R3 = H; X = N, R1 = F, R2 = Me, R3 = H] exhibited good exposure and oral bioavailability in mouse pharmacokinetic (PK) study. Compound I [X = C, R1 = Cl, R2 = R3 = H] was selected for further profiling and revealed comparable mouse and rat GSNOR potency, high selectivity against alc. dehydrogenase (ADH) and carbonyl reductase (CBR1) family of enzymes, low efflux ratio and permeability in PAMPA, a high permeability in CALU-3 assay, significantly low hERG activity and minimal off-target activity. Further, an in-vivo efficacy of compound I [X = C, R1 = Cl, R2 = R3 = H] was disclosed in cigarette smoke (CS) induced mouse model for COPD. Bioorganic & Medicinal Chemistry Letters published new progress about Alcohol dehydrogenase inhibitors. 887266-99-1 belongs to class iodides-buliding-blocks, and the molecular formula is C7H3FIN, HPLC of Formula: 887266-99-1.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

D’Auria, Maurizio; Mauriello, Giacomo published the artcile< Bis(trifluoroacetoxy)iodobenzene-iodine system: an efficient and selective reagent for iodination of thiophene derivatives>, Application In Synthesis of 88105-22-0, the main research area is iodination thiophene trifluoroacetoxyiodobenzene iodide.

Bis-(trifluoroacetoxy)iodobenzene-iodine system is a good iodinating reagent of thiophene derivatives giving products with iodine atom in α-position on the thiophene ring. For example, iodination of 2-thiophenecarboxylic acid Me ester with bis(trifluoroacetoxy)iodobenzene/iodine gave 5-iodo-2-thiophenecarboxylic acid Me ester in 78% yield.

Tetrahedron Letters published new progress about Iodination, regioselective. 88105-22-0 belongs to class iodides-buliding-blocks, and the molecular formula is C6H5IO2S, Application In Synthesis of 88105-22-0.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Bag, Subhendu Sekhar; Talukdar, Sangita; Anjali, S. J. published the artcile< Regioselective and stereoselective route to N2-β-tetrazolyl unnatural nucleosides via SN2 reaction at the anomeric center of Hoffer's chloro-sugar>, Related Products of 887266-99-1, the main research area is transition state nucleophilic substitution nucleoside tetrazole preparation crystal structure; regioselective stereoselective substitution DNA nucleoside tetrazole steric effect DFT; 2,5-Disubstituted tetrazoles; Regioselective; S(N)2 reaction; Stereoselective; Tetrazolyl-N2-β-nucleosides.

We are reporting a regioselective and stereoselective route to N2-β-tetrazolyl aromatic donor/acceptor unnatural nucleosides as new class of possible DNA base analogs. The SN2 substitution reaction at the anomeric center of Hoffer’s chloro-sugar with various 5-substituted aromatic tetrazoles in THF in presence of K2CO3 proceeds with regioselectivity at N2-tetrazoles and stereoselectivity at α-chloro-sugar with very good yield. The stereoelectronic and steric effects play a crucial role for the observed outcome which is also supported from a theor. DFT study. The methodol. is simple, eco-compatible and the tetrazolyl unnatural nucleosides might find applications in decorating DNA for various biotechnol. and DNA based material science applications.

Bioorganic & Medicinal Chemistry Letters published new progress about Crystal structure. 887266-99-1 belongs to class iodides-buliding-blocks, and the molecular formula is C7H3FIN, Related Products of 887266-99-1.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Klimankova, Iveta; Hubalek, Martin; Matousek, Vaclav; Beier, Petr published the artcile< Synthesis of water-soluble hypervalent iodine reagents for fluoroalkylation of biological thiols>, Application In Synthesis of 1391728-13-4, the main research area is fluoroalkyl iodonium benzoiodoxole preparation water soluble fluoroalkylation reagent; stability chemoselectivity fluoroalkylation thiol cysteine fluoroalkyl iodonium benzoiodoxole.

Water-soluble fluoroalkyl iodonium compounds and fluoroalkyl benzoiodanes were prepared and tested for their ability to alkylate the sulfur atoms of cysteine and cysteine-containing peptides under biocompatible conditions. Some of the reagents displayed excellent reactivity despite their limited stability in aqueous media. In reactions with a cysteine-containing heptapeptide, in addition to the expected S-fluoroalkylated product, a range of side-products were obtained, with the amounts of side-products depending on the conditions used (type of reagent, concentration, and pH). With highly activated hypervalent iodine reagents, a new reactive mode was observed – reaction with disulfides to form fluoroalkyl thiols.

Organic & Biomolecular Chemistry published new progress about Disulfides Role: RCT (Reactant), RACT (Reactant or Reagent). 1391728-13-4 belongs to class iodides-buliding-blocks, and the molecular formula is C9H10FIO, Application In Synthesis of 1391728-13-4.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Brea, Oriana; Szabo, Kalman J.; Himo, Fahmi published the artcile< Mechanisms of Formation and Rearrangement of Benziodoxole-Based CF3 and SCF3 Transfer Reagents>, SDS of cas: 1391728-13-4, the main research area is benziodoxole based trifluoromethyl trifluoromethylthio group transfer reagent formation rearrangement.

Togni’s benziodoxole-based reagents are widely used in trifluoromethylation reactions. It has been established that the kinetically stable hypervalent iodine form (I-CF3) of the reagents is thermodynamically less stable than its acyclic ether isomer (O-CF3). On the other hand, the trifluoromethylthio analog exists in the thermodynamically stable thioperoxide form (O-SCF3), and the hypervalent form (I-SCF3) has been elusive. Despite the importance of these reagents, very little is known about the reaction mechanisms of their syntheses, which has hampered the development of new reagents of the same family. Herein, we use d. functional theory calculations to understand the reasons for the divergent behaviors between the CF3 and SCF3 reagents. We demonstrate that they follow different mechanisms of formation and that the metals involved in the syntheses (potassium in the case of the trifluoromethyl reagent and silver in the trifluoromethylthio analog) play key roles in the mechanisms and greatly influence the possibility of their rearrangements from the hypervalent (I-CF3, I-SCF3) to the corresponding ether-type form (O-CF3, O-SCF3).

Journal of Organic Chemistry published new progress about Free energy of activation. 1391728-13-4 belongs to class iodides-buliding-blocks, and the molecular formula is C9H10FIO, SDS of cas: 1391728-13-4.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Lindstroem, Stefan; Ripa, Lena; Hallberg, Anders published the artcile< Synthesis of Two Conformationally Constrained Analogues of the Minor Tobacco Alkaloid Anabasine>, Quality Control of 188057-20-7, the main research area is anabasine spiro analog preparation.

The anabasine analogs spiro[4-azaindan-1,2′-piperidine] and spiro[6-azaindan-1,2′-piperidine] have been prepared A series of palladium-catalyzed reactions, where an intramol. cyclization constituted a key reaction, were utilized for the preparation of the two target compounds

Organic Letters published new progress about Cyclization. 188057-20-7 belongs to class iodides-buliding-blocks, and the molecular formula is C5H4INO, Quality Control of 188057-20-7.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com