Journal of Chemical Research

5-[4-(Dialkyoxyphosphorylamino)]phenyl-10,15,20- triphenylporphyrinato gold(III)chlorides have been synthesised and evaluated for their in vitro cytotoxic activity against SMMC-7721 human hepatic and sarcoma 180 mouse cancer cell line panels. 5-[4-(Diisopropoxyphosphorylamino)]phenyl-10,15,20- triphenylporphyrinato gold(III)chloride exhibited significant growth inhibitory properties against sarcoma 180 mouse cancer cells (IC₅₀ value = 2.60 μM) and 5-[4-(dipropoxyphosphorylamino)]phenyl-10,15,20-triphenylporphyrinato gold(III)chloride showed significant growth inhibitory properties against SMMC-7721 human hepatic cancer cells (IC₅₀ value = 5.10 μM).

The complex [N(CH₃)₄]₃[Mn₃Zn₂(3,5-dibromosalox)₃O(N₃)₆Cl₂] has been synthesised and characterised. It crystallises as two independent molecules and exhibits a planar [Mn^III₃-(μ₃-oxo)] core as well as μ₂-η₁:η₁-azide bridging geometry. DNA binding studies show that the complex binds with DNA through intercalation.

A three-component reaction between 2-naphthol, an aryl aldehydes and thioacetamide catalysed by p-toluenesulfonic acid under reflux conditions provided a simple and efficient one-pot route for the synthesis of 1-[aryl(thioacetamido)methyl]-2-naphthol derivatives in excellent yields.

A chiral salen Mn (III) complex has been immobilised onto zirconium aminophosphonates by axial coordination with different linkage arm lengths (CH₂) _n (n = 2–6), to give a series of heterogeneous catalysts. The catalysts exhibited good to excellent catalytic efficiency in the asymmetric epoxidation of α–methylstyrene. One heterogeneous catalyst, with n = 6, gave higher catalytic properties than the original chiral salen Mn (III) complex in the NaClO/PPNO system. It can be easily recovered and reused several times without significant loss of activity.

Reaction of the rigid ligand 2,3,5,6-tetraiodo-1,4-benzenedicarboxylic acid (H₂BDC–I₄) with Ni^II chloride in different solvents affords two coordination polymers {[Ni(BDC–I₄)(MeOH)₄](H₂BDC–I₄)(MeOH)₂}_n and {[Ni(BDC–I₄)(DMF)₂(H₂O)₂] (DMF)₂(H₂O)}_n. Both complexes have one-dimensional, linear coordination networks extended by the exo-bidentate bridging ligands, and also have supramolecular architectures through secondary hydrogen-bonding interactions. Their spectroscopic and thermal properties have also been investigated.

The reaction of CdCl₂·2H₂O with temozolomide (TMZ) affords the complex [Cd(TMZ)Cl₂]_n, whose structure has been characterised by IR spectroscopy, elemental analysis and X-ray single crystal diffraction analysis. It crystallises in the orthorhombic system and space group Pbca, with a = 17.491(4), b = 6.8100(14), c = 18.989(4) Å, V = 2261.9(8) ų, Z = 8, D_calc = 2.217 g cm⁻³, F(000) = 1456, μ(MoKα)= 2.402 mm⁻¹. In this preparation, the temozolomide did not undergo ring-opening as has been seen in previously reported reactions.

A new ent-kaurane diterpenoid named serrin D and seven known compounds were isolated from the aerial parts of Isodon serra. The structure of the new compound was elucidated by various spectroscopic techniques. Five of the compounds were tested for their cytotoxicity towards HL60, SMMC-7721 and Hela cells.

A simple, economical, and environmentally friendly copper-catalysed direct oxidative C–N coupling of 2-aminopyridines with β-keto esters using air as oxidation agent for the creation of imidazo[1,2-a]pyridine-3-carboxylates is demonstrated. Imidazo[1,2-a]pyridine is the basic skeleton for a wide range of biological and pharmacological compounds.

The formation of metal complexes with acid hydrazides plays an important role in the growth of their biological activity. A simple synthetic strategy is described for the synthesis of novel 1,2,4-tri-azepine and 1,2,5-triazocine derivatives via electron donor–acceptor interaction. Thus when 2-aminobenzohydrazide reacted with tetracyanoethylene (TCNE) and 2-dicyanomethylene-indan-1,3-dione (CNIND) afforded 1,2,4-triazepine derivatives. While on reacting 1 with 2,3-dicyano-5,6-dichloro-1,4-benzoquinone (DDQ), 2,3-dichloro-1,4-naphthoquinone (DCHNQ), 1,4-naphthoquinone and/or 2,3,5,6-tetrabromo-1,4-benzoquinone, 1,2,5-triazocine derivatives were formed.

The synthesis of a novel calixarene-based chiral phase-transfer catalyst derived from cinchonine has been achieved in four steps from p-t-butylcalix[4]arene. Its catalytic properties were evaluated over a range of conditions by carrying out the phase-transfer alkylation of N-(diphenylmethylene)glycine t-butyl ester with benzyl bromide. Under the optimal conditions the alkylated product was formed in 96% yield with 91% ee.

Microwave-assisted synthesis of ferrocenyl pyrrolizidines containing cyano groups has been accomplished in moderate yields via a facile [3+2]-cycloaddition reaction of several azomethine ylides, derived from aromatic aldehydes and proline, with 1, 1-dicyano-2-ferrocenylethene as the dipolarophile. This method offers several advantages such as short reaction time and simple procedure.

KAl(SO₄)₂.12H₂O (Alum) is an eco-friendly, inexpensive, readily available and reusable and was applied as catalyst to the synthesis of N-alkyl amides from nitriles and alcohols by the Ritter reaction. This solvent-free procedure is very simple with excellent yields and easy work-up.

Incubation of 19-nortestosterone 1 with Aspergillus wentii MRC 200316 for 5 days afforded 10β-hydroxy-19-nortestosterone 2 (2%), 6β-hydroxy-19-nortestosterone 3 (60%), and 14α-hydroxy-19-nortestosterone 4 (5%).

The transformation of 3-methoxyphenylacetone to 4-amino-3-methoxypropiophenone is described.

The Cu(II) coordination polymer, {[Cu(p-bdc)(4,4′-bpt)]}_n shows a 2D layer structure bridged by a p-bdc anion and the polymer {[Cu(H₂btc)(3,3′-bpt)₂(H₂O)₂]·2H₂O}_n, whose thermal stability has been briefly investigated, shows a 1D chain structure bridged by an H₂btc anion. [p-H₂bdc = 1,4-benzenedicarboxylate acid, H₄btc = 1,2,4,5-benzenetetracarboxylic acid, 4,4′-bpt = 1H-3,5-bis(4-pyridyl)-1,2,4-triazole, 3,3′-bpt = 1H-3,5-bis(3-pyridyl)-1,2,4-triazole] Both complexes have been prepared by the reaction of the relevant carboxylate acid and positional isomeric triazole–bipyridine ligand with Cu(II) salts under hydrothermal conditions. Both structures are further extended through intermolecular interaction to form 3D supramolecular frameworks.

The synthesis of a number of structurally related estradiol-17α-ylmethyl hydroxycinnamides and of one novel estra-1,3,5(10),6-tetraen-3-ol-17β-yl hydroxycinnamide is described, using a microwave assisted amidation of steroidal amines with pentafluorophenol activated, non-protected hydroxycinnamic acids as a key step. A selection of the compounds and of other estra-1,3,5(10)-trien-3-ol 17β-yl hydroxycinnamides was screened against 60 human cancer cell lines, derived from nine neoplastic diseases. From the overall results of the screening, it could be inferred that dihydroxycinnamide derived estradiol conjugates exhibit a better cytotoxic profile when compared with hydroxymethoxycinnamide derived estradiol conjugates.

A mild and practical synthetic route for biphenyls is established. Isopropyl nitrite was prepared from sodium nitrite, isopropanol and hydrochloric acid. The biphenyl compounds were obtained from the diazotisation of aniline derivatives with the generated isopropyl nitrite and the coupling reaction with benzene derivatives in the presence of CuCl as a catalyst in good yields.

The one-pot reaction of an aryl aldehyde with 2-cyanopyridine and ammonium acetate in refluxing acetic acid produced the known 2-(2′-pyridyl)imidazole and fused imidazoles. This suggests that the steric effect of aryl rings plays an important role in these syntheses. A possible mechanism of the reaction is discussed.

The compound [Me₄bim][CdCl₄] (Me₄bim = 1,1′,3,3′-tetramethyl-2,2′-bi-1H-imidazolium), has been prepared via a solvothermal reaction and has an isolated (0-D) structure. It displays an emission in the blue region that is ascribed to ligand-to-ligand charge transfer on the basis of a theoretical investigation.