40420-05-1Relevant articles and documents
Multistep Synthesis and in Vitro Anticancer Evaluation of 2-Pyrazolyl-Estradiol Derivatives, Pyrazolocoumarin-Estradiol Hybrids and Analogous Compounds
Adamecz, Dóra Izabella,Frank, éva,Kiricsi, Mónika,Krishna Gopisetty, Mohana,Molnár, Barnabás
, (2020/09/18)
Although the hormone independent cytotoxic activity of several estradiol derivatives endowed with a simple substituent at C-2 has been reported so far, 2-heterocyclic and 2,3-condensed analogs are less investigated from both synthetic and pharmacological points of view. Therefore, novel A-ring-connected 2-pyrazoles of estradiol and, for comparison, their structurally simplified non-steroidal pairs were synthesized from estradiol 3-methyl ether and 6-methoxy-1,2,3,4-tetrahydronaphthalene. Friedel-Crafts acetylation of the protected phenolic compounds and subsequent O-demethylation led to ortho-substituted derivatives regioselectively, which were converted to arylhydrazones with phenylhydrazine, 4-tolylhydrazine and 4-chloro-phenylhydrazine, respectively, under microwave conditions. The hydrazones were subjected to cyclization with the Vilsmeier-Haack reagent immediately after preparation and the ring closure/formylation sequence resulted in steroidal and non-steroidal 40-formylpyrazoles in moderate to good yields. During reductive transformations, 4-hydroxymethyl-pyrazoles were obtained, while oxidative lactonization of the 4-formylpyrazole moiety with the phenolic OH in the presence of the Jones reagent afforded A-ring-integrated pyrazolocoumarin hybrids and related analogs. Steroidal pyrazoles, which were produced as C-17 acetates due to acetylation of C-17 OH during the primary Friedel-Crafts reaction, underwent deacetylation in alkaline methanol to furnish 2-heterocyclic estradiol derivatives. Pharmacological studies revealed the overall and cancer cell-specific cytotoxicity of the derivatives and the half maximal inhibitory concentrations were obtained for the most promising compounds.
De Novo Synthesis of Phenols and Naphthols through Oxidative Cycloaromatization of Dienynes
Rong, Ming-Guang,Qin, Tian-Zhu,Liu, Xin-Rui,Wang, Hong-Fa,Zi, Weiwei
supporting information, p. 6289 - 6293 (2018/10/09)
In this work, a rhodium-catalyzed oxidative cycloaromatization of dienynes, which provides a highly straightforward and efficient way to access polysubstituted naphthols and phenols under mild conditions, is described. Challenged electron-withdrawing groups are well tolerated in this protocol, and late-stage phenyl ring formation is demonstrated.
Exploring naphthyl-carbohydrazides as inhibitors of influenza A viruses
Barman, Sanmitra,You, Lei,Chen, Ran,Codrea, Vlad,Kago, Grace,Edupuganti, Ramakrishna,Robertus, Jon,Krug, Robert M.,Anslyn, Eric V.
, p. 81 - 90 (2014/01/06)
A library of hydrazide derivatives was synthesized to target non-structural protein 1 of influenza A virus (NS1) as a means to develop anti-influenza drug leads. The lead compound 3-hydroxy-N-[(Z)-1-(5,6,7,8-tetrahydronaphthalen-2-yl) ethylideneamino]naphthalene-2-carboxamide, which we denoted as "HENC", was identified by its ability to increase the melting temperature of the effector domain (ED) of the NS1 protein, as assayed using differential scanning fluorimetry. A library of HENC analogs was tested for inhibitory effect against influenza A virus replication in MDCK cells. A systematic diversification of HENC revealed the identity of the R group attached to the imine carbon atom significantly influenced the antiviral activity. A phenyl or cyclohexyl at this position yielded the most potent antiviral activity. The phenyl containing compound had antiviral activity similar to that of the active form of oseltamivir (Tamiflu), and had no detectable effect on cell viability.
Annelation of Baylis-Hillman derivatives: Synthesis of highly functionalised tetrahydronaphthalenes
J'mour, Asma,Rezgui, Farhat
experimental part, p. 642 - 644 (2011/02/26)
PTSA-promoted Robinson annelation of a-(3-oxobutyl)cyclohex-2-en-1-one derivatives in refluxing toluene, affords efficiently in a one pot process a variety of hydroxytetrahydronaphthyl carbonyl compounds in good yields. Further highly regioselective elect
Structure-affinity studies for a novel series of homochiral naphtho and tetrahydronaphtho analogues of α1 antagonist WB-4101
Bolchi, Cristiano,Catalano, Paolo,Fumagalli, Laura,Gobbi, Marco,Pallavicini, Marco,Pedretti, Alessandro,Villa, Luigi,Vistoli, Giulio,Valoti, Ermanno
, p. 4937 - 4951 (2007/10/03)
A number of enantiomeric pairs of naphthodioxane, tetrahydronaphthodioxane and naphthoxy analogues of WB-4101 (1) were designed and synthesized in order to improve the selectivity profile of the parent compound, hopefully in favour of the α1a-AR with respect to the other two α1 subtypes and the 5-HT1A receptor. The new compounds 2-8 and, in addition, the two enantiomers of 1 were tested in binding assays on the α1a-AR, α1b-AR, α1d-AR, and the 5-HT1A receptor. Two of them, namely the naphtho- and tetrahydronaphthodioxane derivatives (S)-2 and (S)-3, showed lower, but significantly more specific α1a affinity than (S)-1, while the two enantiomers of the 2-methoxy-1-naphthoxy analogue 6 maintained most of the very high α1a affinity of (S)-1 and its α1a versus α1b selectivity slightly increasing the α1a/α1d and α1a/5HT 1A affinity ratios. The SAR data were evaluated in the light of known α1 subtype pharmacophores and of the α1a-AR binding mode of WB-4101 resultant from literature mutagenesis studies disclosing some interesting consonances with these models.
Novel flavanoids as chemotherapeutic, chemopreventive, and antiangiogenic agents
-
, (2008/06/13)
Novel compounds are useful as chemotherapeutic, chemopreventative, and antiangiogenic agents are provided. The compounds are flavanoids, including flavanones, flavanols, and chalcones. The compounds have the structure of formula (I) 1wherein R1 through R3 and R5 through R11 are defined herein, and α, β, and γ are optional bonds, providing that when α is absent, β is present, and when β is absent, α is present. When α is present, preferred R4 moieties are selected from O, S, NH and CH2, and when α is absent, preferred R4 groups are selected from OH, SH, NH2 and CH3. When γ is present, the preferred R5 substituent is O, while when γ is absent, the preferred R5 substituent is OH. Pharmaceutical compositions are provided as well, as are methods of synthesis and use.
Titanium(IV) chloride-mediated ortho-acylation of phenols and naphthols
Bensari, Ahlem,Zaveri, Nurulain T.
, p. 267 - 271 (2007/10/03)
The use of titanium(IV) chloride as a Lewis acid for direct ortho-acylation of phenols and naphthols proves to be a convenient, more general and direct route to various hydroxyaryl ketones. The route is regioselective, leading to ortho C-acylated products in satisfactory to high yields in most cases.
Zirconium tetrachloride as a mediator for ambient temperature ortho-Fries rearrangements
Harrowven, David C.,Dainty, Richard F.
, p. 7659 - 7660 (2007/10/03)
Zirconium tetrachloride has been found to be an excellent mediator of the Fries reaction. Rearrangements occur at ambient temperature and are highly selective; giving the acetophenone derived from acetyl migration to the sterically least encumbered adjacent carbon.
Lead(IV) Ester and Electrochemical Oxidations of Phenolic Compounds: a Comparative Study
Begley, Michael J.,Gill, G. Bryon,Pattenden, Gerald,Stapleton, Alan,Raphael, Richard A.
, p. 1677 - 1684 (2007/10/02)
Oxidation of 3-acetyl-1-propyl-5,6,7,8-terahydro-2-naphthol (6) with lead(IV) acetate or lead(IV) benzoate is shown to produce almost entirely the o-quinol esters, (8) and (20), respectively.By contrast, electrochemical oxidation of (6) in acetic acid at
Research on nitro-derivatives of biological interest. XXVIII. Synthesis of hydrogenated analogs of 2-nitronaphthofuranes and activities against microorganisms
Einhorn,Demerseman,Rene,et al.
, p. 79 - 84 (2007/10/02)
The authors describe the various ways of transforming 5.6.7.8-tetrahydro 1- and 2-naphthols to 2-nitro 6.7.8.9-tetrahydronaphtho[2.1-b]furan, 2-nitro 5.6.7.8-tetrahydronaphtho[2.3-b]furan and 2-nitro 6.7.8.9-tetrahydronaphtho[1.2-b]furan as well as their derivatives methylated on the furan ring. Although the hydrogenated analogues of 2-nitronaphthofurans are less active than 2-nitronaphthofurans against bacteria, they tend to be more efficacious against protozoa. Their methylated derivatives are particularly efficient against these latter.
