Category: 104-03-0

Ye, Chen-Xi published the artcileStereocontrolled 1,3-nitrogen migration to access chiral ¦Á-amino acids, COA of Formula: C8H7NO4, the publication is Nature Chemistry (2022), 14(5), 566-573, database is CAplus and MEDLINE.

Here a protocol for the economical and practical synthesis of optically active ¦Á-amino acids RNHC(R¹)(R²)C(O)OH (R = Ts, Ms, C(O)OMe, (2,2,2-trichloroethoxy)carbonyl; R¹ = H, Me; R² = pent-2-yn-1-yl, 4-methylphenyl, 2H-1,3-benzodioxol-5-yl, etc.) based on an unprecedented stereocontrolled 1,3-nitrogen shift was reported. The method employs abundant and easily accessible carboxylic acids R¹CH(R²)C(O)OH as starting materials, which are first connected to a nitrogenation reagent, followed by a highly regio- and enantioselective ruthenium- or iron-catalyzed C(sp³)-H amination. This straightforward method displays a very broad scope, providing rapid access to optically active ¦Á-amino acids with aryl, allyl, propargyl and alkyl side chains, and also permits stereocontrolled late-stage amination of carboxylic-acid-containing drugs and natural products.

Nature Chemistry published new progress about 104-03-0. 104-03-0 belongs to catalysis-chemistry, auxiliary class Nitro Compound,Carboxylic acid,Benzene, name is 4-Nitrophenylacetic acid, and the molecular formula is C14H21BO2, COA of Formula: C8H7NO4.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Bhela, Irene preet published the artcileTritylamine as an Ammonia Surrogate in the Ugi Reaction Provides Access to Unprecedented 5-Sulfamido Oxazoles Using Burgess-type Reagents, SDS of cas: 104-03-0, the publication is Organic Letters (2021), 23(9), 3610-3614, database is CAplus and MEDLINE.

Starting from a wide range of ¦Á-acylamino amide substructures RNHC(O)CH(R¹)NHC(O)R² (R = pentyl, Bn, [3-(1H-1,3-benzodiazol-1-ylmethyl)phenyl]methyl, etc.; R¹ = H, Me, n-Pr, hexyl; R² = Me, Ph, (4-nitrophenyl)methyl, etc.) synthesized using tritylamine as an ammonia surrogate in the Ugi reaction, Burgess-type reagents R³N^–S(O)₂N⁺(CH₂CH₃)₃ (R³ = C(O)OMe, C(O)OBn) enable cyclodehydration and afford unprecedented oxazole scaffolds I with four points of diversity, including a sulfamide moiety in the 5-position. The synthetic procedure employs readily available starting materials and proceeds smoothly under mild reaction conditions with good tolerance for a variety of functional groups, coming to fill a gap in the field of oxazole compounds

Organic Letters published new progress about 104-03-0. 104-03-0 belongs to catalysis-chemistry, auxiliary class Nitro Compound,Carboxylic acid,Benzene, name is 4-Nitrophenylacetic acid, and the molecular formula is C8H7NO4, SDS of cas: 104-03-0.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Watanabe, Hiroyuki published the artcileSynthesis and biological evaluation of radioiodinated 3-phenylcoumarin derivatives targeting myelin in multiple sclerosis, Product Details of C8H7NO4, the publication is Bioorganic & Medicinal Chemistry Letters (2020), 30(24), 127562, database is CAplus and MEDLINE.

Myelin is a lipid multilayer involved in the rate of nerve transmission, and its loss is a pathol. feature of multiple sclerosis in brains. Since in vivo imaging of myelin may be useful for drug development, early diagnosis, and monitoring the disease stage, the authors designed, synthesized, and evaluated eight novel radioiodinated 3-phenylcoumarin derivatives as imaging probes targeting myelin. In the biodistribution study using normal mice, all compounds displayed sufficient brain uptake, ranging from 2.5 to 5.0% ID/g, at 2 min postinjection. On ex vivo autoradiog., 6-[¹²⁵I]- and 7-[¹²⁵I]-labeled (dimethylaminophenyl)coumarins showed high binding affinity for myelin in the normal mouse brain. In addition, the radioactivity accumulation of the 7-[¹²⁵I]-labeled (dimethylaminophenyl)coumarin in the white matter of the spinal cord in the exptl. autoimmune encephalomyelitis mice was lower than that in naive mice. These results suggest that a 7-[¹²³I]-labeled (dimethylaminophenyl)coumarin shows potential as a single photon emission computed tomog. probe targeting myelin.

Bioorganic & Medicinal Chemistry Letters published new progress about 104-03-0. 104-03-0 belongs to catalysis-chemistry, auxiliary class Nitro Compound,Carboxylic acid,Benzene, name is 4-Nitrophenylacetic acid, and the molecular formula is C6H13I, Product Details of C8H7NO4.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Sakharov, Pavel A. published the artcileRegiodivergent Synthesis of Butenolide-Based ¦Á- and ¦Â-Amino Acid Derivatives via Base-Controlled Azirine Ring Expansion, Product Details of C8H7NO4, the publication is Organic Letters (2020), 22(8), 3023-3027, database is CAplus and MEDLINE.

A series of 5-aminobutenolides I [R¹ = Me, Ph, 4-ClC₆H₄, 3,4-(MeO)₂C₆H₃, etc.; R² = MeO, 1-pyrrolidinyl; R³ = MeO₂C, Ph, 4-O₂NC₆H₄, 2-thienyl, etc.] and II (R¹ = MeO₂C, Ph, 4-BrC₆H₄, etc.; R² = MeO, Ph, 1-pyrrolidinyl; R³ = MeO₂C, 4-ClC₆H₄, 4-O₂NC₆H₄) has been synthesized from 2-bromo-2H-azirine-2-carboxylic esters/amides III and arylacetic acids R³CH₂CO₂H. The reaction regioselectivity can be switched by a change of the basic catalyst, making it possible to prepare both butenolide-based ¦Á- and ¦Â-amino acid derivatives I and II. The change in the regioselectivity is interpreted in terms of the stability and reactivity of the enolates formed during the S_N²‘ substitution of the bromine in the azirine by the carboxylate ion.

Organic Letters published new progress about 104-03-0. 104-03-0 belongs to catalysis-chemistry, auxiliary class Nitro Compound,Carboxylic acid,Benzene, name is 4-Nitrophenylacetic acid, and the molecular formula is C8H7NO4, Product Details of C8H7NO4.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Nelson, Hope published the artcilePractical Chemoselective Acylation: Organocatalytic Chemodivergent Esterification and Amidation of Amino Alcohols with N-Carbonylimidazoles, SDS of cas: 104-03-0, the publication is Angewandte Chemie, International Edition (2021), 60(42), 22818-22825, database is CAplus and MEDLINE.

Here, the N-carbonylimidazoles enable catalytic chemodivergent aniline or alc. acylation in the presence of pyridinium ions or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), was reported. Both acylation reactions display high and broad chemoselectivity for the target group. Unprecedented levels of chemoselectivity were observed in the DBU-catalyzed esterification: A single esterification product was obtained from a mol. containing primary aniline, alc., phenol, secondary amide, and N-H indole groups. These acylation reactions are highly practical as they involve only readily available, inexpensive, and relatively safe reagents; can be performed on a multigram scale; and can be used on carboxylic acids directly by in situ formation of the acylimidazole electrophile.

Angewandte Chemie, International Edition published new progress about 104-03-0. 104-03-0 belongs to catalysis-chemistry, auxiliary class Nitro Compound,Carboxylic acid,Benzene, name is 4-Nitrophenylacetic acid, and the molecular formula is C8H7NO4, SDS of cas: 104-03-0.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Zhang, Haoqi published the artcileSynthesis of Novel Heterocycles by Amide Activation and Umpolung Cyclization, Related Products of catalysis-chemistry, the publication is Organic Letters (2020), 22(6), 2376-2380, database is CAplus and MEDLINE.

Herein, we report a metal-free synthesis of cyclic amidines, oxazines, and an oxazinone under mild conditions by electrophilic amide activation. This strategy features an unusual Umpolung cyclization mode and enables the smooth union of ¦Á-aryl amides and diverse alkylazides, effectively rerouting our previously reported ¦Á-amination transform.

Organic Letters published new progress about 104-03-0. 104-03-0 belongs to catalysis-chemistry, auxiliary class Nitro Compound,Carboxylic acid,Benzene, name is 4-Nitrophenylacetic acid, and the molecular formula is C8H6KNO4S, Related Products of catalysis-chemistry.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Aprile, Silvio published the artcile1,2,4-Oxadiazole-Bearing Pyrazoles as Metabolically Stable Modulators of Store-Operated Calcium Entry, Application of 4-Nitrophenylacetic acid, the publication is ACS Medicinal Chemistry Letters (2021), 12(4), 640-646, database is CAplus and MEDLINE.

Store-operated calcium entry (SOCE) is a pivotal mechanism in calcium homeostasis, and, despite still being under investigation, its dysregulation is known to be associated with severe human disorders. SOCE modulators are therefore needed both as chem. probes and as therapeutic agents. While many small mols. have been described so far, their poor properties in terms of drug-likeness have limited their translation into the clin. practice. In this work, we describe the bioisosteric replacement of the ester moiety in pyrazole derivatives with a 1,2,4-oxadiazole ring as a means to afford a class of modulators with high metabolic stability. Moreover, among our derivatives, a compound able to increase the calcium entry was identified, further enriching the library of available SOCE activators.

ACS Medicinal Chemistry Letters published new progress about 104-03-0. 104-03-0 belongs to catalysis-chemistry, auxiliary class Nitro Compound,Carboxylic acid,Benzene, name is 4-Nitrophenylacetic acid, and the molecular formula is C8H7NO4, Application of 4-Nitrophenylacetic acid.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Liu, Hong-Chuan published the artcileSynthesis and Cytotoxicity Assessment of Novel 7-O- and 14-O-Derivatives of Glaucocalyxin A, Synthetic Route of 104-03-0, the publication is Anti-Cancer Agents in Medicinal Chemistry (2020), 20(10), 1241-1249, database is CAplus and MEDLINE.

Background: Rabdosia japonica has been historically used in China as a popular folk medicine for the treatment of cancer, hepatitis, and gastricism. Glaucocalyxin A (GLA), an ent-kaurene diterpene isolated from Rabdosia japonica, is one of the main active ingredients showing potent inhibitory effects against several types of tumor cells. To the best of our knowledge, studies regarding the structural modification and Structure- Activity Relations (SAR) of this compound have not yet been reported. Objective: The aim of this study was to discover more potent derivatives of GLA and investigate their SAR and cytotoxicity mechanisms. Methods: Novel 7-O- and 14-O-derivatives of GLA were synthesized by condensation of acids or acyl chloride. The anti-tumor activities of these derivatives against various human cancer cell lines were evaluated in vitro by MTT assays. Apoptosis assays of compound 17 (7,14-diacylation product) were performed on A549 and HL-60 cells by flow cytometry and TUNNEL. The acute toxicity of this compound was tested on mice, at the dose of 300mg per kg body weight Results: Seventeen novel 7-O- and 14-O-derivatives of GLA (1-17) were synthesized. These compounds showed potent cytotoxicity against the tested cancer cell lines, and almost all of them were found to be more cytotoxic than GLA and oridonin. Of the synthesized derivatives, compound 17 presented the greatest cytotoxicity, with IC50 values of 0.26¦ÌM and 1.10¦ÌM in HL-60 and CCRF-CEM cells, resp. Furthermore, this compound induced weak apoptosis of A549 cells but showed great potential in stimulating the apoptosis of HL- 60 cells. Acute toxicity assays indicated that compound 17 is relatively safer. Conclusion: The results reported herein indicate that the synthesized GLA derivatives exhibited greater cytotoxicity against leukemia cells than against other types of tumors. In particular, 7,14-diacylation product of GLA was found to be an effective anti-tumor agent. However, the cytotoxicity mechanism of this product in A549 cells is expected to be different than that in other tumor cell lines.

Anti-Cancer Agents in Medicinal Chemistry published new progress about 104-03-0. 104-03-0 belongs to catalysis-chemistry, auxiliary class Nitro Compound,Carboxylic acid,Benzene, name is 4-Nitrophenylacetic acid, and the molecular formula is C8H7NO4, Synthetic Route of 104-03-0.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Patel, Dushyant V. published the artcileNovel carbazole-stilbene hybrids as multifunctional anti-Alzheimer agents, Related Products of catalysis-chemistry, the publication is Bioorganic Chemistry (2020), 103977, database is CAplus and MEDLINE.

Mols. capable of engaging with multiple targets associated with pathol. condition of Alzheimer’s disease have proved to be potential anti-Alzheimer’s agents. The goal to develop multitarget-directed ligands for the treatment of Alzheimer’s disease, a novel series of carbazole-based stilbene derivatives (E)-I [R = H, NH₂, 4-chlorobutanamidyl, 4-(pyrrolidin-1-yl)butanamidyl, ([3-(piperidin-1-yl)propyl]carbamoyl)azanyl, etc.; R¹ = H, NO₂, NH₂, 2-chloroacetamidyl, ([2-(pyrrolidin-1-yl)ethyl]carbamothioyl)azanyl, etc.] was designed by the fusion of carbazole ring with stilbene scaffold. The designed compounds (E)-I were synthesized and evaluated for their anti-AD activities including cholinesterase inhibition, A¦Â aggregation inhibition, antioxidant and metal chelation properties. Amongst them, (E)-I [R = H; R¹ = ([2-(pyrrolidin-1-yl)ethyl]carbamothioyl)azanyl, (A)] appeared to be the best candidate with good inhibitory activities against AChE (IC₅₀ value of 2.64¦ÌM) and BuChE (IC₅₀ value of 1.29¦ÌM), and significant inhibition of self-mediated A¦Â_1-42 aggregation (51.29% at 25¦ÌM concentration). The metal chelation study showed that compound (A) possessed specific copper ion chelating property. Addnl., compound (A) exhibited moderate antioxidant activity. To understand the binding mode of (A), mol. docking studies were performed, and the results indicated strong non-covalent interactions of (A) with the enzymes in the active sites of AChE, BuChE as well as of the A¦Â_1-42 peptide. Addnl., it showed promising in silico ADMET properties. Putting together, these findings evidently showed compound (A) as a potential multitarget-directed ligand in the course of developing novel anti-AD drugs.

Bioorganic Chemistry published new progress about 104-03-0. 104-03-0 belongs to catalysis-chemistry, auxiliary class Nitro Compound,Carboxylic acid,Benzene, name is 4-Nitrophenylacetic acid, and the molecular formula is C8H7NO4, Related Products of catalysis-chemistry.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Li, Ya-Lan published the artcileChemo- and Site-Selective Fischer Esterification Catalyzed by B(C₆F₅)₃, Related Products of catalysis-chemistry, the publication is Asian Journal of Organic Chemistry (2021), 10(6), 1424-1427, database is CAplus.

A direct and catalytic dehydrative esterification of carboxylic acids RC(O)OH [R = hept-1-yn-1-yl, 2-(naphthalen-2-yl)ethyl, (1-methyl-1H-indol-3-yl)methyl, 1-([(benzyloxy)carbonyl]amino)ethyl, etc.] with alcs. R¹OH (R¹ = Et, cyclohexyl, 2,3-dihydroxypropyl, etc.) is described. B(C₆F₅)₃ is shown to be a highly effective catalyst for the Fischer esterification, providing esters RC(O)OR¹ in high to excellent yields. This esterification shows excellent chemo- and site-selective monoesterification of various polyols R¹OH without any protection step, including bio-derived mol. glycerol.

Asian Journal of Organic Chemistry published new progress about 104-03-0. 104-03-0 belongs to catalysis-chemistry, auxiliary class Nitro Compound,Carboxylic acid,Benzene, name is 4-Nitrophenylacetic acid, and the molecular formula is C8H7NO4, Related Products of catalysis-chemistry.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia