An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
The syntheses of N,S-substituted 4-chloro-2-mercapto-5-methylbenzenesulfonamide derivatives are described. The compounds 6-11,14,15 and 19-22 were tested for their in vitro anticancer activity against 9 human cancer cell lines. The most active compounds 6, 9 and 20 showed moderate cytotoxic activity and were approximately 5-fold less potent than cisplatin.
Background: N-substituted 3-amino-1H-indazoles represent an interesting class of biologically active compounds. Among them, derivatives containing phenylurea moiety are of particular interest. Such compounds have been found to possess inhibitory activity against cancer cell growth. Additionally, various oxazoline-containing compounds have also been designed as potential anticancer agents. Objective: The aim of this work was to obtain a new class of N-substituted 3-amino-1H-indazole derivatives with cytotoxic activity towards cancer cells. Method: Two series of 1-[1-(4,5-dihydrooxazol-2-yl)-1H-indazol-3-yl]-3-phenylurea and 3- phenylthiourea derivatives 7-17 and 18-22, respectively, were prepared and screened for their potential in vitro cytotoxic activities against lung carcinoma LCLC-103H cell line using a crystal violet microtiter plate assay. Results: All the urea derivatives, except the compound 8, were inactive at a concentration of 20 μM attainable in cancer cells, while the thiourea derivatives showed a pronounced cancer cell growth inhibitory effects. The most potent 1-[1-(4,5-dihydrooxazol-2-yl)-1H-indazol-3-yl]-3-ptolylthiourea (19) exhibited cytotoxicity on the lung cancer LCLC-103H and cervical cancer SISO cell lines at a concentration of 10 µM. Moreover, compound 19 displayed cytostatic activity against pancreas cancer DAN-G cell line. Conclusion: The 1-[1-(4,5-dihydrooxazol-2-yl)-1H-indazol-3-yl]-3-phenylthiourea derivatives described herein may serve as a useful scaffold for the search for novel anticancer agents. Keywords: Alzheimer's disease, anticancer agents, Cytotoxic activity, 1-[1-(4, 5-dihydrooxazol-2-yl)-1H-indazol-3-yl]-3- phenylureas, 1-[1-(4, 5-dihydrooxazol-2-yl)-1H-indazol-3-yl]-3-phenylthioureas, synthesis.
Four copper(II) complexes, C1–4, derived from 1-(isoquinolin-3-yl)heteroalkyl-2-one ligands L1–4 were synthesized and characterized using an elemental analysis, IR spectroscopic data as well as single crystal X-ray diffraction data for complex C1. The stability of complexes C1–4 under conditions mimicking the physiological environment was estimated using UV-Vis spectrophotometry. The antiproliferative activity of both ligands L1–4 and copper(II) compounds C1–4 were evaluated using an MTT assay on four human cancer cell lines, A375 (melanoma), HepG2 (hepatoma), LS-180 (colon cancer) and T98G (glioblastoma), and a non-cancerous cell line, CCD-1059Sk (human normal skin fibroblasts). Complexes C1–4 showed greater potency against HepG2, LS180 and T98G cancer cell lines than etoposide (IC50 = 5.04–14.89 μg/mL vs. IC50 = 43.21–>100 μg/mL), while free ligands L1–4 remained inactive in all cell lines. The prominent copper(II) compound C2 appeared to be more selective towards cancer cells compared with normal cells than compounds C1, C3 and C4. The treatment of HepG2 and T98G cells with complex C2 resulted in sub-G1 and G2/M cell cycle arrest, respectively, which was accompanied by DNA degradation. Moreover, the non-cytotoxic doses of C2 synergistically enhanced the cytotoxic effects of chemotherapeutic drugs, including etoposide, 5-fluorouracil and temozolomide, in HepG2 and T98G cells. The antimicrobial activities of ligands L2–4 and their copper(II) complexes C2–4 were evaluated using different types of Gram-positive bacteria, Gram-negative bacteria and yeast species. No correlation was found between the results of the antiproliferative and antimicrobial experiments. The antioxidant activities of all compounds were determined using the DPPH and ABTS radical scavenging methods. Antiradical tests revealed that among the investigated compounds, copper(II) complex C4 possessed the strongest antioxidant properties. Finally, the ADME technique was used to determine the physicochemical and drug-likeness properties of the obtained complexes.
Indole derivatives with therapeutic propertiesThe bicyclic ring system of indole (benzo[b]pyrrole) is a structural element of many therapeutic agents used in medical practice with diverse biological activities, including anticancer, antibacterial, antiviral, anti-inflammatory, analgesic, antipyretic and hypotensive drugs as well as antidepressants or antipsychotics.Indole compounds, both natural and synthetic, have long been used as anticancer drugs in the treatment of neoplastic diseases such as lung cancer, breast cancer, sarcomas, lymphomas, and tumors of the central nervous system.On the other hand, as antiemetic drugs, they are used in oncological patients undergoing chemotherapy and radiotherapy.Indole compounds regulate the functioning of the endocrine system and are used in the treatment of hyperprolactinemia, endometriosis, and central premature children's puberty.They are important for the proper functioning of the nervous system and therefore are used in patients suffering from neurodegenerative diseases, such as Parkinson's or Alzheimer's disease.The indole ring is also the basis of drugs used, among others, in cardiovascular diseases -in the treatment of arterial hypertension, in the digestive system -in irritable bowel syndrome, in the respiratory system in particular in the case of asthma as well as in bone tissue diseases indicated for the treatment of osteoporosis.Indole derivatives are in the focus of many research centers, in which their new properties are constantly being discovered.It should be emphasized, that aromatic or heteroaromatic rings constituting the structural motif of compounds with different pharmacological effects are referred to as privileged structures.This group of heterocyclic compounds also includes indole.This article is intended to provide a review of currently used drugs containing the heterocyclic indole system in their structures and their possible clinical applications.The current directions of searching for novel indole-based drugs are also presented.
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
