52927-22-7Relevant articles and documents
Process for Preparing Nafamostat Mesilate and Intermediate Thereof
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Paragraph 0080-0081, (2021/10/27)
The present invention provides a method for efficiently producing astaxmostat mesylate through a simple process and a method for producing 6 - amidino -2 - naphthol mesylate in high yield under mild conditions.
Decarboxylative Hydroxylation of Benzoic Acids
Ritter, Tobias,Su, Wanqi,Xu, Peng
, p. 24012 - 24017 (2021/10/06)
Herein, we report the first decarboxylative hydroxylation to synthesize phenols from benzoic acids at 35 °C via photoinduced ligand-to-metal charge transfer (LMCT)-enabled radical decarboxylative carbometalation. The aromatic decarboxylative hydroxylation is synthetically promising due to its mild conditions, broad substrate scope, and late-stage applications.
A facile and versatile electro-reductive system for hydrodefunctionalization under ambient conditions
Huang, Binbin,Guo, Lin,Xia, Wujiong
supporting information, p. 2095 - 2103 (2021/03/26)
A general electrochemical system for reductive hydrodefunctionalization is described, employing the inexpensive and easily available triethylamine (Et3N) as a sacrificial reductant. This protocol is characterized by facile operation, sustainable conditions, and exceptionally wide substrate scope covering the cleavage of C-halogen, N-S, N-C, O-S, O-C, C-C and C-N bonds. Notably, the selectivity and capability of reduction can be conveniently switched by simple incorporation or removal of an alcohol as a co-solvent.
Iodine(III)-Mediated, Controlled Di- or Monoiodination of Phenols
Satkar, Yuvraj,Yera-Ledesma, Luisa F.,Mali, Narendra,Patil, Dipak,Segura-Quezada, Luis A.,Ramírez-Morales, Perla I.,Solorio-Alvarado, César R.,Navarro-Santos, Pedro
, p. 4149 - 4164 (2019/04/30)
An oxidative procedure for the electrophilic iodination of phenols was developed by using iodosylbenzene as a nontoxic iodine(III)-based oxidant and ammonium iodide as a cheap iodine atom source. A totally controlled monoiodination was achieved by buffering the reaction medium with K3PO4. This protocol proceeds with short reaction times, at mild temperatures, in an open flask, and generally with high yields. Gram-scale reactions, as well as the scope of this protocol, were explored with electron-rich and electron-poor phenols as well as heterocycles. Quantum chemistry calculations revealed PhII(OH)·NH3 to be the most plausible iodinating active species as a reactive "I+" synthon. In light of the relevance of the iodoarene moiety, we present herein a practical, efficient, and simple procedure with a broad functional group scope that allows access to the iodoarene core unit.
C -Glycosylation of Substituted β-Naphthols with Trichloroacetimidate Glycosyl Donors
Chakraborty, Soumen,Mal, Dipakranjan
, p. 1560 - 1568 (2018/01/17)
Several glycosyl donors have been systematically investigated for C-glycosylation of substituted β-naphthols to delineate the effect of the substituents. Whereas glycosylations of the parent 2-naphthol are smoothly achievable, those of differently substituted 2-naphthols are cumbersome. Efficiency of the glycosylation depends on the nature of both the glycosyl donors and the substituents of the arene ring. Among various glycosyl donors, trichloroacetimidate glycosyl donors are found to be superior for glycosylation with substituted 2-naphthols.
3-Aryl-1,2,4-oxadiazole Derivatives Active Against Human Rhinovirus
Kim, Jinwoo,Shin, Jin Soo,Ahn, Sunjoo,Han, Soo Bong,Jung, Young-Sik
, p. 667 - 672 (2018/05/14)
The human rhinovirus (hRV) is the causative agent of the common cold that often aggravates respiratory complications in patients with asthma or chronic obstructive pulmonary disease. The high rate of mutations and variety of serotypes are limiting the development of anti-hRV drugs, which emphasizes the need for the discovery of novel lead compounds. Previously, we identified antiviral compound 1 that we used here as the starting material for developing a novel compound series with high efficacy against hRV-A and -B. Improved metabolic stability was achieved by substituting an ester moiety with a 1,2,4-oxadiazole group. Specifically, compound 3k exhibited a high efficacy against hRV-B14, hRV-A21, and hRV-A71, with EC50 values of 66.0, 22.0, and 3.7 nM, respectively, and a relevant hepatic stability (59.6 and 40.7% compound remaining after 30 min in rat and human liver microsomes, respectively). An in vivo study demonstrated that 3k possessed a desirable pharmacokinetic profile with low systemic clearance (0.158 L·h-1·kg-1) and modest oral bioavailability (27.8%). Hence, 3k appears to be an interesting candidate for the development of antiviral lead compounds.
Synthesis and cytotoxicity of n-substituted dibenzo[a,j]xanthene-3,11-dicarboxamide derivatives
Song, Yongbin,Yang, Yihui,Wu, Lijun,Dong, Naiwei,Gao, Shang,Ji, Hongrui,Du, Xia,Liu, Bo,Chen, Guoyou,Dembinski, Roman
, (2017/04/03)
In order to study the structure-activity relationships of xanthene derivatives, four series of N-substituted 14-aryl-14H-dibenzo[a,j]xanthene-3,11-dicarboxamide derivatives were synthesized. The structures of all compounds were identified by 1H-NMR HR-MS and IR spectra in which compounds 6a-h were further identified by 13C-NMR spectra. The in vitro antitumor activity of the synthesized compounds was tested by MTT assay. Most of them displayed strong inhibitory activity on human hepatocellular carcinoma cell lines (SK-HEP-1 HepG2 and SMMC-7721 cells) and acute promyelocytic leukemia NB4 cells. Compounds 6c-6e exhibited significant inhibitory activity against NB4 cells with IC50 values of 0.52 μM and 0.76 μM respectively much lower than 5.31 μM of the positive control As2O3.
Methanesulfonic acid the naphthalene not takes charge of he intermediate — 6 - amidino - 2 - naphthol armor sulfonate synthetic method
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Paragraph 0008; 0009, (2017/12/30)
The present invention relates to a new synthesis method for a nafamostat mesylate intermediate 6-amidino-2-naphthol methanesulfonate. According to the new method, 6-hydroxy-2-naphthaldehyde is adopted as a raw material, dimethyl sulfoxide is adopted as a reaction solvent, the dimethyl sulfoxide and hydroxylamine hydrochloride are subjected to an addition elimination reaction to obtain 6-cyano-2-naphthol, the 6-cyano-2-naphthol is subjected to a pinner reaction in a HCl/methanol solution to obtain 6-hydroxy-2-naphthalene imino methyl ester hydrochloride, ammonia gas is introduced to carry out an aminolysis reaction to obtain 6-amidino-2-naphthol, and the 6-amidino-2-naphthol sequentially reacts with sodium bicarbonate and methanesulfonic acid to convert into the 6-amidino-2-naphthol methanesulfonate. According to the present invention, in the new synthesis method, the 6-cyano-2-naphthol preparation in the first step adopts the completely-new method, the use of the highly toxic copper cyanide in the traditional method is avoided, the operations are simple, and the conditions are mild; and the second step adopts the improved pinner method, wherein the reaction of acetyl chloride and methanol is adopted to produce HCl to replace direct introduction of HCl gas into the reaction system, such that the improved method has strong operability and industrialization is easily achieved.
Design, Conformation, and Crystallography of 2-Naphthyl Phenyl Ethers as Potent Anti-HIV Agents
Lee, Won-Gil,Chan, Albert H.,Spasov, Krasimir A.,Anderson, Karen S.,Jorgensen, William L.
supporting information, p. 1156 - 1160 (2016/12/16)
Catechol diethers that incorporate a 7-cyano-2-naphthyl substituent are reported as non-nucleoside inhibitors of HIV-1 reverse transcriptase (NNRTIs). Many of the compounds have 1-10 nM potencies toward wild-type HIV-1. An interesting conformational effect allows two unique conformers for the naphthyl group in complexes with HIV-RT. X-ray crystal structures for 4a and 4f illustrate the alternatives.
Emission and transient absorption measurements of substitution effects of C-C triple bonds on relaxation processes of the fluorescent state of naphthalenes
Yamaji, Minoru,Maeda, Hajime,Minamida, Keita,Maeda, Tomohiro,Asai, Kengo,Konishi, Gen-Ichi,Mizuno, Kazuhiko
, p. 321 - 345 (2013/03/14)
Photophysical and photochemical properties of naphthalenes substituted with trimethylsilylethynyl, tert-butylethynyl, and trimethylsilylbutadiynyl groups were investigated by measurement of fluorescence yields, lifetimes, and triplet absorption. Introducing trimethylsilylethynyl and tert-butylethynyl groups to the 1-position of the naphthalene skeleton substantially enhanced fluorescence and intersystem crossing (ISC). The rates of fluorescence of 2-substituted naphthalenes were low. The effect of ethynyl groups on the 1-substituted naphthalenes was rationalized in terms of an increase of the transition moment along the short axis of the naphthalene skeleton. Substitution of the trimethylsilylbutadiynyl group at the 1 or 2-position of the naphthalene skeleton caused a considerable decrease in the fluorescence yield (approximately 0.01) and an increase in the ISC yield (0.99).
