- One step synthesis of N-[1-(2-diethylaminoethylamino)-7-(H or methoxy)-9-oxo-9H-thioxanthen-4-ylmethyl]-formamides and, acetamide from their corresponding alcohols, hycanthone, and 7-methoxy-hycanthone
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N-[1-(2-Diethylamino-ethylamino)-7-(H or methoxy)-9-oxo-9H-thioxanthen-4-ylmethyl]-formamides and acetamide were synthesized from their corresponding alcohols, hycanthone and 7-methoxyhycanthone, in one step procedure and 45% yield.
- He, Hua-Zhong,Kwon, Chul-Hoon
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- Thioxanthenone antitumor agents
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Compounds having anti-tumour activity are disclosed having the formulawherein: (1) n is 2 or 3;R1 and R2 are independently lower-alkyl;Q is a residue chosen from the group consisting ofCH2NHR3, CH2N(R4)SO2R7, CH2NHCHO, CH=N-Ar,C(O)NR5R6, CH2N(R4)C(O)R7, CH2N(C2H5)CHO,CH2N(R4)P(O)(O-lower-alkyl)2, CH2N=CH-N(R9)(R10),CH2N(R4)C(O)CF3 and CH2N(R4)C(O)OR7;R3 is hydrogen or lower-alkyl;R4 is hydrogen, lower-alkyl or Ar;R5 is hydrogen, lower-alkyl or Ar;R6 is hydrogen or lower-alkyl;R7 is lower-alkyl, or Ar;R8 is hydroxy;Ar is phenyl or phenyl substituted with methyl, methoxy, hydroxy, halogen or nitro; andR9 and R10 are independently lower-alkyl; or(2) Q is a residue chosen from the group consisting of CH2N(R4)SO2R7, CH=N-Ar, C(O)NR5R6, CH2N(R4)C(O)R7, CH2N(R4)P(O)(O-lower-alkyl)2, CH2N(R4)C(O)CF3 and CH2N(R4)C(O)OR7; R8 is hydrogen, lower-alkyl, lower-alkoxy, or hydroxy; Ar is phenyl substituted by hydroxy; and n, R1, R2, R4, R5, R6, and R7 are as defined hereinabove in part (1) with the proviso that one or more of R4, R5, or R7 is Ar; or(3) Q is a residue chosen from the group consisting of CH2N=CH-N(R9)(R10) and CH2N(R4)C(O)CF3 ; R8 is hydrogen, lower-alkyl, lower-alkoxy, or hydroxy; and n, R1, R2, R4, R7, Ar, R9 and R10 are as defined hereinabove in part (1), or a pharmaceutically acceptable acid-addition salt or solvate thereof . Compositions containing the thioxanthenones and methods of treating tumors and cancer in mammals with the thioxanthenones are also disclosed.
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- Synthesis and antitumor activity of 4-aminomethylthioxanthenone and 5- aminomethylbenzothiopyranoindazole derivatives
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Two new series of antitumor agents, 4-aminomethylthioxanthenones (9-50) and 5-amino-methylbenzothiopyranoindazoles (51-61), are described and compared. Nearly all members of both series display excellent in vivo activity versus murine pancreatic adenocarcinoma 03 (Panc03) although there is little to distinguish the two series from each other. In both series there is no discernible relationship between structure and in vivo efficacy. Selected analogues were evaluated in vitro; all were observed to have moderate to strong DNA binding via intercalation. However, varying degrees of in vitro P388 cytotoxicity and topoisomerase II inhibition were seen. In general, those molecules which exhibited strong topoisomerase II inhibition were significantly more cytotoxic than those which did not. In both series, those derivatives (45-50, 60, and 61) having a phenolic hydroxy substitution exhibited the most potent P388 cytotoxicity and topoisomerase II inhibition.
- Perni, Robert B.,Wentland, Mark P.,Huang, Jianhua I.,Powles, Ronald G.,Aldous, Suzanne,Klingbeil, Kristina M.,Peverly, A. Danielle,Robinson, Ronald G.,Corbett, Thomas H.,Jones, Julie L.,Mattes, Kenneth C.,Rake, James B.,Coughlin, Susan A.
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p. 3645 - 3654
(2007/10/03)
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- Thioxanthenone antitumor agents
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1-[[(Dialkylamino)alkyl]amino]-4-substituted-thioxanthen-9-ones are disclosed as antitumor agents. Compositions containing the thioxanthenones and methods of treating tumors and cancer in mammals with the thioxanthenones are also disclosed.
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