Acetylenic derivatives are an important class of compounds since many of them display interesting biological activities and possess anticancer, antibacterial, antimicrobial, HIV-inhibitory properties. The synthetic methods for their preparation are of interest especially with regard to the synthesis of enediyne antibiotics [1-3]. The natural enediynes are the most potent of anticancer agents discovered, some members of which are three order of magnitude more potent than other anticancer drugs but their clinical use has been limited because of their toxicity and modest selectivity for cancer cells. It has prompted several research groups to design, prepare, and test new simplified, fully synthetic acetylenic analogues, characterized by a similar mode of action [1-4].

As an extension of our work on the development of anticancer drugs, we synthesized the series of new 3,4-disubstituted thioquinolines 1 possessing propargyl, 2-butynyl, 4-bromo(chloro)-2-butynyl and 4-substituted-2-butynyl groups with the aim to obtain more information about the influence of substituents on antiproliferative activity in this class of compounds.

The obtained compounds were tested for their antiproliferative activity in vitro against the cells of human (colon SW 707, leukemia CCRF/CEM, breast T 47D) and murine (leukemia P388, melanoma B 16) cancer cell lines. The most active compounds have the ID₅₀ values ranging from 0,43 to 4,00 mg/ml comparable to that of referential cis-platin.

[1]. K.Nicolaou, W.-M. Dai, Angew. Chem. Int. Ed. Engl., 30, 1387 (1991).

[2]. G.B.Jones, F.S.Found, Curr. Pharm. Design., 8, 2415 (2002).

[3]. S. Boryczka, W.Mól, A.Jowsa, Wiad. Chem., 61, 275 (2007).

[4]. W.Mól, A.Naczyński, S.Boryczka, J.Wietrzyk, A.Opolski, Pharmazie, 61, 742 (2006).

This study was supported by Polish Ministry of Science and Higher Education (Grant No. N405 036 31/2655).

• Legal notice:
  

  Copyright (c) Pielaszek Research, all rights reserved.
  The above materials, including auxiliary resources, are subject to Publisher's copyright and the Author(s) intellectual rights. Without limiting Author(s) rights under respective Copyright Transfer Agreement, no part of the above documents may be reproduced without the express written permission of Pielaszek Research, the Publisher. Express permission from the Author(s) is required to use the above materials for academic purposes, such as lectures or scientific presentations.
  In every case, proper references including Author(s) name(s) and URL of this webpage: https://science24.com/paper/14822 must be provided.

1. Synthesis of new 5H-indolo[2,3-b]quinoline derivatives with a high selective cytotoxic activity
2. Synthesis, structure and anticancer activity of alkynyl derivatives of betulin
3. Administration of isothiocyanate-derived mercapturic acids inhibits solid tumor growth of 4T1 murine mammary carcinoma cells in BALB/c mice
4. Preliminary studies on application of library of artificial receptors for differentiation of metabolites in urine of healthy and cancer mice
5. Starch derivatives as vehicles for drug delivery in anticancer therapy
6. Mercapturic acids as a naturally occurring isothiocyanates prodrug form with site-directed delivery system built-in based on an oxidative environment of the tumor
7. Synthesis and biological activity of novel N,N-cyclic-2,4-dihydroxythiobenzamide derivatives
8. Anticancer activity of vitamin D, genistein and indoloquinoline analogs
9. Antiproliferative activity of novel acetylenic derivatives of betulin against G-361 human melanoma cells
10. Synthesis and anticancer activity of acetylenic derivatives of betulin
11. Crystal structures of betulin and its derivatives
12. Interaction of endotoxin and polymyxin B in B16 mouse melanoma model of metatstasis
13. Anticancer activity of the conjugates:  modified fibrinogen – methotrexate.
14. Synthesis and cytotoxic activity of new Pt (II) complexes with nitropyrazoles in aerobic and hypoxic conditions
15. Vitamin D analogs enhance the activity of imatinib mesylate in human non-small cell lung cancer model
16. Colon cancer treatment with the use of vitamin D analogs and irinotecan 
17. Novel bifunctional synthetic isothiocyanates with high antiproliferative activity
18. Naturally occurring hydroxyalkyl isothiocyanates and isothiocyanatoalkyl benzoates - structure-activity and structure-mechanism of action relationship studies.
19. Synthesis and biological evaluation of new amino acid and dipeptide derivatives of neocryptolepine as anticancer agents. 
20. Antitumor activity of carrier-methotrexate conjugates.
21. CLA derivatives as functional food compounds
22. New acetylenic derivatives of betulin with anticancer activity
23. Catalytic synthesis and antiproliferative activity in vitro of polisubstituted isoxazolopyridine derivatives.
24. Steroid profile of Asplenium cuneifolium
25. The influence of (24R)-1,24- dihydroxyvitamin D₃ on the anticancer activity of 5-fluorouracil in human colon cancer model
26. Comparison of antiproliferative activity of the natural isothiocyanates and their mercapturic derivatives.
27. Could the calorically restricted ketogenic diet be an     effective alternative or supportive therapy for breast cancer?
28. Analogs of genistein and its possible anti-metastatic properties
29. The influence of novel analogs of vitamin D₃ on the antiproliferative activity of cisplatin or doxorubicin on human promyelocytic leukaemia cell line HL-60 
30. New amino acid and peptide derivatives of 5H-indolo[2,3-b]quinoline and their biological activity.
31. The cytotoxic activity of glycosides of indolo[2,3-b]quinoline derivatives.
32. Disubstituted indolo[2,3-b]quinoline derivatives - the cytotoxic activity in vitro against various human tumor cell lines.
33. Mono substituted 5H- and 6H-indolo[2,3-b]quinoline derivatives and their ability to overcome the barrier of drug resistance.
34. New calcipotriol analogs, their toxicity and antitumor activity in vivo in comparison to the affinity with VDR and DBP
35. Synthesis and cytostatic activity of new 1-substituted 6H-pyrido[4,3-b]carbazole derivatives
36. The new analogs of genistein decrease mitochondrial membrane potential and activate caspase-3
37. New amino acid derivatives of 6H-indolo[2,3-b]quinolines
38. Influence of Transformation of the Amino Group in Anthracyclines into -N=CH-N< or -N=CH-O- Group on Their Biological Properties
39. PRIMARY CYTOTOXICITY EVALUATION OF NEW HETEROCYCLIC SYSTEMS WITH PYRIDODIAZEPINE.
40. SYNTHESIS AND ANTIPROLIFERATIVE ACTIVITY IN VITRO OF NEW 2-AMINOBENZIMIDAZOLE DERIVATIVES. PART 3. REACTIONS OF 2-ARYLIDENE- AMINOBENZIMIDAZOLE WITH SELECTED 1,3-DIKETONES.
41. CONJUGATED LINOLEIC ACIDS PREPARATIONS AS EFFECTIVE NUTRACEUTICS
42. INVESTIGATIONS OF LIPOPHILICITY OF ANTICANCER-ACTIVE THIOQUINOLINE DERIVATIVES
43. THE ANTIMETASTATIC EFFECT OF BACTERIOPHAGE T4* ADMINISTRATED IN COMBINED TREATMENT WITH SELECTED CYTOSTATICS IN MICE WITH B16 MELANOMA
44. SYNTHESIS AND ANTIPROLIFERATIVE ACTIVITY OF DIACETYLENIC THIOQUINOLINES
45. SYNTHESIS AND CYTOTOXIC ACTIVITY OF 10-DEACETYL-10-PROPARGILPACLITAXEL
46. THE CYTOTOXIC GLYCOSIDES OF INDOLO[2,3-B]QUINOLINE DERIVATIVES. IN VITRO AND IN VIVO STUDIES
47. MONO SUBSTITUTED 5H-INDOLO[2,3-B]- QUINOLINE DERIVATIVES AND THEIR ABILITY TO OVERCOME THE BARRIER OF DRUG RESISTANCE.
48. DISUBSTITUTED INDOLO[2,3-b]QUINOLINE DERIVATIVES. THE CYTOTOXIC ACTIVITY IN VITRO AGAINST VARIOUS HUMAN TUMOR CELL LINE.
49. ANTITUMOR EFFECT OF CISPLATIN OR FLUOROURACIL IN COMBINED TREATMENT WITH (24R)-1,24-DIHYDROXYVITA- MIN D₃
50. FIRST ROUND STUDIES ON LEWIS LUNG CARCINOMA ACTIVITY OF THE NEW LEAD STRUCTURES IN THE ISOXAZOLE HETEROCYCLIC SYSTEM
51. GENISTEIN, ITS NEW ANALOGS AND COMPLEXES - THE ANTIPROLIFERATIVE EFFECTS ON HL-60 LEUKEMIA CELL LINE
52. COMBINATION OF: IMATINIB, PRI-2191 AND CYTOSTATICS - THE ANTIPROLIFERATIVE EFFECTS ON HL-60 LEUKEMIA CELL LINE
53. ANTIPROLIFERATIVE ACTIVITY IN VITRO OF DIASTEREOMERIC ANALOGUES OF VITAMIN D3 AGAINST NORMAL AND CANCER CELL LINES