Effect of stereochemistry on the anti-HIV activity of chiral thiourea compounds

Venkatachalam, T. K.; Chen, Mao; Uckun, Fatih M.

doi:10.1016/j.bmc.2004.04.050

Cited by 139 publications

(86 citation statements)

References 12 publications

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“…Moreover, several adamantanebased drugs are currently employed as important medications against malaria infections [7], central nervous disorders [8][9][10], hyperglycaemia [11] and drug-resistant TB strain infections [12]. In addition, thiourea derivatives were reported to display marked antitumor [13], anti-HIV [14], antimalarial [15] and antimicrobial [16] activities. As a part of our current research interest in the pharmacological [17][18][19] and structural [20][21][22] properties of adamantane derivatives, we report herein the synthesis and crystal structure of the title compound as bioactive agent and as precursor for adamantanebased chemotherapeutic agents.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 1-(adamantan-1-yl)-3-(4-bromophenyl)thiourea, C₁₇H₂₁BrN₂S

et al. 2016

Zeitschrift Für Kristallographie - New Crystal Structures

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C17H 21 BrN 2 S, orthorhombic, Pbca (No. 61), a = 17.0675(7) Å, CCDC no.: 1449483The asymmetric unit of the crystal structure is shown in the gure. Tables 1 and 2 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters. Source of materialTo a solution of 1-adamantylamine (1.51 g, 0.01 mol) in ethanol (15 mL), 4-bromophenyl isothiocyanate (2.14 g, 0.01 mol) was added and the mixture was heated under re ux for three hours. On cooling, the precipitated crude product was ltered, dried and crystallized from ethanol to yield 3.36 g (92%) of the title compound (C17H 21 BrN 2 S) as transparent block crystals. M.P.:

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Section: Discussionmentioning

confidence: 99%

Crystal structure of 1-(adamantan-1-yl)-3-(4-bromophenyl)thiourea, C₁₇H₂₁BrN₂S

et al. 2016

Zeitschrift Für Kristallographie - New Crystal Structures

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“…Recently, same derivatives have been reported to be effective against HIV [6,7]. Futhermore, the pyrazoles with the groups of chloride and trifluoromethyl, like 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulphenylpyrazole or 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfonylpyrazole, show good bioactivities, too [1].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of N-[1-(2,6-dichloro-4-trifluoromethyl)phenyl-3- cyano-1H-pyrazol-5-yl]-N'-4-methoxybenzoyl thioureas, C20H12Cl2F3N5O2S

Zhang¹,

Zhong²

2009

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialFollowing the method of [1] reaction of 2,6-dichloro-4-trifluoromethylamine (0.01 mol) with a suspension of nitrosyl sulfuric acid, followed by reaction with a solution of ethyl 2,3-dicyanopropionate (0.01 mol) in acetic acid, gave the title compound (about 0.005 mol) (1). Further more, according to the method [2], 4-methoxy-benzoyl chlordie (0.007 mol) with dry potassium thiocyanate (0.1.mol) was refluxed in anhydrous CH 3 CN for 2 h at the temperature 80 .°C , which was then filtrated to obtain acylisothiocyanate solution (2). The obtained products 1 and 2 were reacted in anhydrous CH 3 CN for about 4 h to get the title compound. Single crystals suitable for X-ray analysis were obtained by slow evaporation of the solution in acetone (m.p. 473 -475 K). IR, 1 H NMR and 13 C NMR data are available in the CIF. Experimental detailsThe H atoms were positioned geometrically and allowed to ride on their parent atoms at distances of d(Csp 2 -H) = 0.93 Å with U iso = 1.2 U eq (parent atom), d(Csp 3 -H) = 0.96 Å with U iso = 1.5 U eq (parent atom). The large U eq of C1 and fluorine atoms as compared to neighbours may be attributed to (rotational) disorder of the CF 3 group fluorine atoms. We want to refine the crystal structure taking into account the disorder, but failed to do it. DiscussionAcyl thiourea derivatives show good bioactivity and may be used in many fields, such as in antimicrobial, sterilization, insecticide and herbicidal [3][4][5]. Recently, same derivatives have been reported to be effective against HIV [6,7]. Futhermore, the pyrazoles with the groups of chloride and trifluoromethyl, like 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulphenylpyrazole or 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfonylpyrazole, show good bioactivities, too [1]. Hence it is necessary to combine these two parts into new acyl thioureas. The molecule of the title compound an acylthioureas with an overall U-shape. In the crystal structure, the dihedral angles between the pyrazole and attached phenyl ring and the methoxyphenyl are 88.9(1)°and 30.5(1)°,r espectively. An intramolecular N4−H4···O1 hydrogen bond with an N4···O1 seperation of 2.577(4) Å,stablizes the molecule.

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“…In addition, thiourea derivatives are recognized as potent anti-Malaria [11], anti-HIV [12], anticancer [13] and antimicrobial [14] agents. As a part of an ongoing research interest in the chemotherapeutic [15][16][17] and structure [18][19][20] of adamantane derivatives, we report herein, the crystal structural of the title compound.…”

Section: Atom Sitementioning

confidence: 99%