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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 19
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Original Articles

Synthesis of 10-Hydroxycamptothecin: Evaluation of New Moderators for the Chemoselective Reduction of Camptothecin

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Pages 2828-2834 | Received 30 Apr 2010, Published online: 29 Jun 2011

REFERENCES

  • Wall , M. E. ; Wani , M. C. ; Cook , C. E. ; Palmer , K. H. Plant antitumor agents, I: The isolation and structure of camptothecin, a novel alkaloidal leukemia, and tumor inhibitor from Camptotheca acuminate . J. Am. Chem. Soc. 1966 , 88 , 3888 – 3890 .
  • Govindachari , T. R. ; Viswanathan , N. 9-Methoxycamptothecin: A new alkaloid from Mappia foetida Miers . Indian J. Chem. 1972 , 10 ( 4 ), 453 – 454 .
  • Wani , M. C. ; Nicholas , A. W. ; Monroe , E. W. Plant antitumor agents. 23: Synthesis and antileukemic activity of camptothecin analogs . J. Med. Chem. 1986 , 29 , 2358 – 2363 .
  • Sawada , S. ; Matsuoka , S. ; Nokata , K. ; Nagata , H. ; Furuta , T. ; Yokokura , T. ; Miyasaka , T. Synthesis and antitumor activity of 20(S)-camptothecin derivatives: A-ring-modified and 7,10-disubstituted camptothecins . Chem. Pharm. Bull. 1991 , 39 , 3183 – 3188 .
  • Wani , M. C. ; Ronman , P. E. ; Lindley , J. T. ; Wall , M. E. Plant antitumor agents, 18: Synthesis and biological activity of camptothecin analogs . J. Med. Chem. 1980 , 23 ( 5 ), 554 – 560 .
  • Wani , M. C. ; Wall , M. E. Plant antitumor agents. II: The structure of two new alkaloids from Camptotheca acuminate . J. Org. Chem. 1969 , 34 , 1364 – 1367 .
  • He , X. ; Lu , W. ; Jiang , X. ; Cai , J. ; Zhang , X. ; Ding , J. Synthesis and biological evaluation of bis and monocarbonate prodrugs of 10-hydroxycamptothecins . Bioorg. Med. Chem. 2004 , 12 ( 15 ), 4003 – 4008 .
  • Hertzberg , R. P. ; Caranfa , M. J. ; Holden , K. G. ; Jakas , D. R. ; Gallagher , G. ; Mattern , M. R. ; Mong , S. M. ; O'Leary Bartus , J. ; Johnson , R. K. ; Kingsbury , W. D. Modification of the hydroxylactone ring of camptothecin: Inhibition of mammalian topoisomerase I and biological activity . J. Med. Chem. 1989 , 32 ( 3 ), 715 – 720 .
  • Jaxel , C. ; Kohn , K. W. ; Wani , M. C. ; Wall , M. E. ; Pommier , Y. Structure–activity study of the actions of camptothecin derivatives on mammalian topoisomerase, I: Evidence for a specific receptor site and a relation to antitumor activity . Cancer Res. 1989 , 49 ( 6 ), 1465 – 1469 .
  • Hsiang , Y. H. ; Liu , L. F. ; Wall , M. E. ; Wani , M. C. ; Nicholas , A. W. ; Manikumar , G. ; Kirschenbaum , S. ; Silber , R. ; Potmesil , M. DNA topoisomerase I–mediated DNA cleavage and cytotoxicity of camptothecin analogs. Cancer Res. 1989, 49 (16), 4385–4389.
  • Kingsbury , W. D. ; Boehm , J. C. ; Jakas , D. R. ; Holden , K. G. ; Hecht , S. M. ; Gallagher , G. ; Caranfa , M. J. ; McCabe , F. L. ; Faucette , L. F. ; Johnson , R. K. ; Hertzberg , R. P. Synthesis of water-soluble (aminoalkyl) camptothecin analogues: Inhibition of topoisomerase I and antitumor activity . J. Med. Chem. 1991 , 34 , 98 – 107 .
  • Hsiang , Y. H. ; Hertzberg , R. ; Hecht , S. ; Liu , L. F. Camptothecin induces protein-linked DNA breaks via mammalian DNA topoisomerase . J. Biol. Chem. 1985 , 260 , 14873 – 14875 .
  • Hsiang , Y. H. ; Liu , L. F. Identification of mammalian DNA topoisomerase I as intracellular target of the anticancer drug camptothecin . Cancer Res. 1988 , 48 , 1722 – 1726 .
  • Wood , J. L. ; Fortunak , J. M. ; Mastrocola , A. R. ; Mellinger , M. ; Burk , P. L. An efficient conversion of camptothecin to 10-hydroxycamptothecin . J. Org. Chem. 1995 , 60 ( 17 ), 5739 – 5740 .
  • Burk , P. L. ; Fortunak , J. M. ; Mastrocola , A. R. ; Mellinger , M. ; Wood , J. L. Process for the preparation of certain 9-substituted camptothecins. U.S. Patent 5734056, 1998 .
  • Shen , W. ; Coburn , C. A. ; Bornmann , W. G. ; Danishefsky , S. J. Concise total syntheses of dl-Camptothecin and related anticancer drugs . J. Org. Chem. 1993 , 58 ( 3 ), 611 – 617 .
  • Eijsbouts , S. ; De Beer , V. H. J. ; Prins , R. Hydrodenitrogenation of quinoline over carbon-supported transition metal sulfides . J. Catal. 1991 , 127 , 619 – 630 .
  • Wilkinson , H. S. ; Hett , R. ; Tanoury , G. J. ; Senanayake , C. H. ; Wald , S. A. Modulation of catalyst reactivity for the chemoselective hydrogenation of a functionalized nitroarene: Preparation of a key intermediate in the synthesis of (R,R)-formoterol tartrate . Org. Process. Res. Dev. 2000 , 4 , 567 – 570 .
  • Cosma , G. ; David , R. ; Schumacher , B. J. Fast deuterium molecules desorbing from metals . Surf. Sci. 1980 , 95 , 210 – 216 .
  • Rendulic , K. D. ; Anger , G. ; Winkler , A. Wide range nozzle beam adsorption data for the systems hydrogen/nickel and hydrogen/palladium(100) . Surf. Sci. 1989 , 208 , 404 – 424 .
  • Burke , M. L. ; Madix , R. J. Hydrogen on palladium(100) sulfur: The effect of sulfur on precursor-mediated adsorption and desorption . Surf. Sci. 1990 , 237 , 1 – 19 .
  • Wilke , S. ; Scheffler , M. Mechanism of poisoning the catalytic activity of Pd(100) by a sulfur adlayer . Phy. Rev. Lett. , 1996 , 76 ( 18 ), 3380 – 3383 .
  • James , B. R. ; Ng , F. T. T. ; Rempel , G. L. Catalytic reduction of dimethylsulfoxide by molecular hydrogen using rhodium(III) complexes . Can. J. Chem. 1969 , 47 , 4521 – 4526 .
  • Acharyulu , P. V. R. ; Sekhar , N. M. ; Lankeshwararao , M. ; Subrahmanyam , V. R. R. Process for preparing irinotecan. U.S. Patent 20070208050, 2007 .
  • Acharyulu , P. V. R. ; Sekhar , N. M. ; Lankeshwararao , M. Process for preparing topotecan. U.S. Patent 7547785 B2, 2009 .

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