2471-70-7Relevant academic research and scientific papers
Design, synthesis and evaluation of naphthalene-2-carboxamides as reversal agents in MDR cancer
Lokhande, Tushar N.,Viswanathan,Joshi, Advait,Juvekar, Aarti
, p. 6022 - 6026 (2006)
A novel class of molecules with structure N-[3-(4-substituted-1-piperazinyl) propyl]-6-methoxy naphthalene-2-carboxamides were designed by generating a pharmacophore for potent MDR reversal activity, using Elacridar (GF 120918) as a query molecule and using MOE software. They were synthesized by condensing 6-methoxynaphthalene-2-carboxylic acid with N-[3-(4-substituted-1-piperazinyl) propyl] amines in the presence of DCC in DMF. They were evaluated in P388 murine lymphocytic leukemia cell line (P388) in vitro using SRB assay for cytotoxicity and in adriamycin-resistant P388 murine lymphocytic leukemia cell line (P388/ADR) using MTT assay for resistant reversal activity. Test compounds were non-toxic at the doses studied (upto 80 μg/ml). They effectively reversed adriamycin resistance at the doses studied (40 and 80 μg/ml). The percentage enhancement in adriamycin activity was in the range 33.58 -90.67 (at 40 μg/ml) and 8.80-46.04 (at 80 μg/ml) and the corresponding reversal potency values were in the range 1.33-1.90 and 1.08-1.46, respectively. Test compounds 2, 3, and 5 exhibited better activity as compared to the standard resistant reversal agent (Verapamil), at same concentration.
Steric Factors in Amide-Directed Metalations of N,N-Dialkyl-6-methoxynaphthalene-2-carboxamides: Synthesis of a Sterically Perturbed Acylnaphthol
Bindal, Rajeshwar D.,Katzenellenbogen, John A.
, p. 3181 - 3185 (1987)
The powerful ortho-metalating directive effect of the N,N-dialkylcarboxamide group can be used for the preparation of C-1 alkyl-substituted 2,6-acylnaphthols.The alternative reaction pathways of C-1 metalation vs. acylation (carbonyl addition) in the reaction of alkyllithium reagents with N,N-dialkyl-6-methoxy-naphthalenecarboxamides depends upon the cumulative steric nature of the N-alkyl and lithium alkyl groups: The N,N-dimethylamide 7 undergoes carbonyl addition with n-BuLi and t-BuLi; the N,N-diethylamide 8, carbonyl addition with n-BuLi, but metalation with t-BuLi; and the N,N-diisopropylamide 9 only C-1 metalation with n-BuLi.Subsequent reaction of the N,N-diethyl-1-ethyl-6-methoxynaphhtalene-2-carboxamide (13) with n-BuLi gives the desired 2,6-acylnaphthyl methyl ether, whereas the corresponding ethylated diisopropylamide 14 undergoes additional metalation on the ethyl group.These 1-ethyl-2-carboxamidonaphthalenes are very sterically crowded and show evidence in the proton NMR of hindered rotation about both the amide bond and the ethyl group.The UV and fluorescence spectra of the acylnaphthols 17 and 18 show the consequences of this steric crowding through reduced conjugation between the acyl group and the naphthalene group.The more hindered 1-ethylated acylnaphthol 18 shows lower molar absorptivity, and it fluoresces only in basic solution.
Carboxylation of Aryl Triflates with CO2 Merging Palladium and Visible-Light-Photoredox Catalysts
Bhunia, Samir Kumar,Das, Pritha,Nandi, Shantanu,Jana, Ranjan
supporting information, p. 4632 - 4637 (2019/06/27)
We report herein a visible-light-promoted, highly practical carboxylation of readily accessible aryl triflates at ambient temperature and a balloon pressure of CO2 by the combined use of palladium and photoredox Ir(III) catalysts. Strikingly, the stoichiometric metallic reductant is replaced by a nonmetallic amine reductant providing an environmentally benign carboxylation process. In addition, one-pot synthesis of a carboxylic acid directly from phenol and modification of estrone and concise synthesis of pharmaceutical drugs adapalene and bexarotene have been accomplished via late-stage carboxylation reaction. Furthermore, a parallel decarboxylation-carboxylation reaction has been demonstrated in an H-type closed vessel that is an interesting concept for the strategic sector. Spectroscopic and spectroelectrochemical studies indicated electron transfer from the Ir(III)/DIPEA combination to generate aryl carboxylate and Pd(0) for catalytic turnover.
The influence of the thioalkyl terminal group on the mesomorphic behavior of some 6-alkoxy-2-naphthoates derived from 1,3,4-oxadiazole
Chothani,Akbari,Patel,Patel
, p. 31 - 46 (2016/07/21)
A new series of mesogenic compounds having a naphthalene moiety has been synthesized by esterification of 4-(5-(alkyllthio)-1,3,4-oxadiazol-2-yl)phenol and 6-alkoxy-2-naphthoic acid and their liquid crystalline properties have been studied. All the members of the series are enantiotropic and exhibit smectic as well as nematic mesophase. The plot of transition temperatures versus number of carbon atoms in the alkoxy chain exhibits no odd even effect and falling tendency for isotropic transition temperatures. High anisotropy, linearity confers rich mesomorphic properties on the system.
Naphthyl, (substituted) aryl, piperazine base trunk apperception composition
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Paragraph 0081; 0082, (2016/10/08)
The invention discloses (substituted) naphthyl, (substituted) aryl, piperazinyl amidine compound with new structures and salt of medical acid, a preparation method and a purification method of the compound and the salt of the medical acid, and a medicine composition containing the compound, wherein the compound has double inhibition activities of 5-hydroxytryptamine (5-HT) reuptake and noradrenalin (NE) reuptake, and shows strong depression resistance in animal experiments. The compound can be used for treating tristimania, and can also be used for treating other nervous system diseases related to the 5-HT and the NE.
N-heterocyclic carbene-assisted, Bis(phosphine)nickel-catalyzed cross-couplings of diarylborinic acids with aryl chlorides, tosylates, and sulfamates
Ke, Haihua,Chen, Xiaofeng,Zou, Gang
, p. 7132 - 7140 (2014/08/18)
Efficient bis(phosphine)nickel-catalyzed cross-couplings of diarylborinic acids with aryl chlorides, tosylates, and sulfamates have been effected with an assistance of N-heterocyclic carbene (NHC) generated in situ from N,N′-dialkylimidazoliums, e.g., N-butyl-N′-methylimidazolium bromide ([Bmim]Br), in toluene using K3PO4·3H2O as base. In contrast to bis(NHC)nickel-catalyzed conventional Suzuki coupling of arylboronic acids, mono(NHC)bis(phosphine)nickel species generated in situ from Ni(PPh3)2Cl2/[Bmim]Br displayed high catalytic activities in the cross-couplings of diarylborinic acids. The structural influences from diarylborinic acids were found to be rather small, while electronic factors from aryl chlorides, tosylates, and sulfamates affected the couplings remarkably. The couplings of electronically activated aryl chlorides, tosylates, and sulfamates could be efficiently effected with 1.5 mol % NiCl2(PPh3)2/[Bmim]Br as catalyst precursor to give the biaryl products in excellent yields, while 3-5 mol % loadings had to be used for the couplings of non- and deactivated ones. A small ortho-substitutent on the aromatic ring of aryl chlorides, tosylates, and sulfamates was tolerable. Applicability of the nickel-catalyzed cross-couplings in practical synthesis of fine chemicals has been demonstrated in process development for a third-generation topical retinoid, Adapalene.
An improved protocol for the oxidative cleavage of alkynes, alkenes, and diols with recyclable Ru/C
Vijay Kumar,Prakash Reddy,Sridhar,Srinivas,Rama Rao
experimental part, p. 739 - 742 (2009/07/18)
Efficient synthesis of carboxylic acids from alkynes; aldehydes from alkenes and diols employing Ru/C-based recyclable catalytic system is reported with good to excellent yields. Georg Thieme Verlag Stuttgart.
SAR studies of capsazepinoid bronchodilators 3: The thiourea part (coupling region) and the 2-(4-chlorophenyl)ethyl moiety (C-region)
Berglund, Magnus,Dalence-Guzman, Maria F.,Skogvall, Staffan,Sterner, Olov
, p. 2529 - 2540 (2008/09/21)
Certain derivatives and analogues of capsazepine are potent in vitro inhibitors of bronchoconstriction in human small airways. During an investigation of the dependency of the potency on the structural features of the capsazepinoids in the thiourea moiety (coupling region) and the 2-(4-chlorophenyl)ethyl moiety (C-region), it was revealed that capsazepinoids with a thiourea or an amide link between the B-ring and the C-region in general have a good bronchorelaxing activity, while urea is a less attractive choice. Further, it was shown that 1,2,3,4-tetrahydroisoquinolines with a 2-(phenyl)ethyl derivative as the C-region are considerably more potent than those with an octyl group, while 2,3,4,5-tetrahydro-1H-2-benzazepines were found to be more insensitive to the nature of the C-region.
Synthesis of aromatic carboxylic acids by carbonylation of aryl halides in the presence of epoxide-modified cobalt carbonyls as catalysts
Boyarskii,Zhesko,Lanina
, p. 1844 - 1848 (2007/10/03)
A new procedure was developed for synthesis of aromatic and heteroaromatic acids and their derivatives (esters, salts) by carbonylation of the corresponding aryl halides. The acids are selectively formed in a high yield under very mild conditions. Highly active catalytic systems, base-containing alcoholic solutions of cobalt carbonyl modified with epoxides, were used to activate aryl halides. 2005 Pleiades Publishing, Inc.
Behavior of naphthoyloxyl and methoxynaphthoyloxyl radicals generated from the photocleavage of dinaphthoyl peroxides and 1-(naphthoyloxy)-2-pyridones
Najiwara, Toshihiro,Hashimoto, Ji-ichiro,Segawa, Katsunori,Sakuragi, Hirochika
, p. 575 - 585 (2007/10/03)
1-Naphthoyloxyl and 2-naphthoyloxyl radicals were generated from photocleavage of dinaphthoyl peroxides and 1-(naphthoyloxy)-2-pyridones in acetonitrile. The difference in product distribution between the precursors is ascribed to the contribution of the two-bond cleavage in the peroxide decomposition in the singlet state. A series of methoxynaphthoyloxyl radicals were also generated from the corresponding (methoxynaphthoyloxy)pyridones and their behavior was compared with that of unsubstituted naphthoyloxyl radicals. The introduction of a methoxy group in the naphthalene ring stabilizes the naphthoyloxyl radicals to prevent their decarboxylation completely and reduces remarkably their reactivities in the addition to olefins and hydrogen-atom abstraction. The structure of the naphthoyloxyl radicals was discussed on the basis of their absorption spectra and MO calculations.
