Dodecanoyl isothiocyanate and <i>N</i>′-(2-cyanoacetyl) dodecanehydrazide as precursors for the synthesis of different heterocyclic compounds with interesting antioxidant and antitumor activity

<p>Dodecanoyl isothiocyanate <b>1</b> was utilized for the construction of thioureido, 2-thioxo-2,3-dihydroquinazolin-4(1<i>H</i>)-one, benzo[<i>d</i>]-1,3-thiazin-4(<i>H</i>)-one and 3-amino quinazolin-4(3<i>H</i>)-one derivatives <b>2, 3, 4</b>, and <b>5</b> respectively. However, <i>N</i>′-(2-cyanoacetyl) dodecanehydrazide <b>6</b> was also used as a key starting material for the construction of a variety of new pyrazolone, pyrazole, thiadiazole, pyridazine, chromeno[2,3-<i>c</i>]pyrazole, and dithiolane derivatives <b>7, 9, 12, 15, 18</b>, and <b>20</b>, respectively. The newly synthesized compounds were characterized by elemental analyses and spectral data (IR, ¹H NMR, and mass spectra). Some of the newly synthesized compounds bearing heterocyclic moieties were tested for antioxidant activity as reflected in their ability to inhibit oxidation in rat brain and kidney homogenates using 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) inhibition. Also, in vitro anticancer activity was examined using the standard (3-(4,5-dimethylthiazolyl-2)-2,5-diphenyltetrazolium bromide) (MTT) method against a panel of two human tumor cell lines namely; hepatocellular carcinoma HepG2 and mammary gland breast cancer MCF-7. Compounds <b>12</b> and <b>16b</b> exhibited the highest activities as antioxidant and antitumor agents. Meanwhile, compounds <b>7</b> and <b>20</b> showed moderate activities and the rest of the tested compounds showed weak activities.</p

Synthesis and Reactions of Novel 2,5-Disubstituted 1,3,4-Thiadiazoles

<div><p></p><p>The desired 1,3,4-thiadiazole compounds bearing different substituents were obtained by the cyclization of the corresponding thiosemicarbazide followed by the reaction with electrophilic reagents, such as aromatic aldehydes, isatin, phenyl isothiocyanate, and carbon disulfide. The newly synthesized 2,5-disubstituted 1,3,4-thiadiazoles were obtained in good yields and their structures were elucidated by spectral data and elemental analysis.</p> <p>[Supplementary materials are available for this article. Go to the publisher's online edition of <i>Synthetic Communications</i>® for the following free supplemental resource(s): Full experimental and spectral details.]</p> </div

Synthesis and antitumor evaluation of novel tetrahydrobenzo[4′,5′]thieno[3′,2′:5,6]pyrimido[1,2-<i>b</i>]isoquinoline derivatives

<p>In the present study, a novel 8,9,10,11-tetrahydro-7<i>H</i>,14<i>H</i>-benzo[4′,5′] thieno[2′,3′:4,5]-1,3-oxazino[3,2-<i>b</i>]isoquinoline-7,14-dione <b>5</b> was prepared by condensation of 2-amino-3-carbethoxy-4,5,6,7-tetrahydrobenzothiophene with homophthalic anhydride under microwave irradiation, followed by alkaline hydrolysis and cyclization using acetyl chloride. Compound <b>5</b> was further allowed to react with different nitrogen nucleophiles to get new tetrahydrobenzothienopyrimido isoquinolinone derivatives. The structures of the prepared compounds were elucidated by IR, ¹H-NMR, ¹³C-NMR, and mass spectroscopy. The newly prepared compounds were tested <i>in vitro</i> against a panel of two human tumor cell lines, namely, hepatocellular carcinoma (liver) HepG2, and mammary gland breast MCF-7. Almost all the tested compounds showed satisfactory activity.</p