An efficient synthesis of a new class of DNA intercalating antitumor 7,10-dihydroxy-6H-pyrazolo[4,5,1-de]acridin-6-ones

Synthesis

Volumn , Issue 6, 1999, Pages 947-952

  Mimura, Takashi ^a   Kato, Nobuyuki ^a   Sugaya, Toru ^a   Ikuta, Masanori ^a,b   Kato, Sachiko ^a   Kuge, Yukihiro ^a   Tomioka, Shinji ^a,b   Kasai, Masaji ^a  

^a KYOWA HAKKO KOGYO CO LTD   (Japan)

^b Kyowa Yuka Co Ltd   (Japan)

Author keywords

Antitumor agents; Process improvement; Pyrazoloacridone

Indexed keywords

5 (3 AMINOPROPYL)AMINO 7,10 DIHYDROXY 2 (2 HYDROXETHYL)AMINOETHYL 6H PYRAZOLO[4,5,1 DE]ACRIDIN 6 ONE DIHYDROCHLORIDE; ACRIDINE DERIVATIVE; ANTINEOPLASTIC AGENT; INTERCALATING AGENT; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 0033030520     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3494     Document Type: Article

References (14)

1. Sugaya, T.; Mimura, Y.; Shida, Y.; Osawa, Y.; Matsukuma, I.; Ikeda, S.; Akinaga, S.; Morimoto, M.; Ashizawa, T.; Okabe, M.; Ohno, H.; Gomi, K.; Kasai, M. J. Med. Chem. 1994, 37, 1028.
2. a) Ikeda, S.; Mimura, Y.; Sugaya, T.; Nakamura, A.; Ashizawa, T.; Akinaga, S.; Ohno, H.; Okabe, M.; Gomi, K.; Kasai, M. In 24th National Medicinal Chemistry Symposium; Abstracts No. 110, Salt Lake City, Utah, USA, 1994.
3. b) Mimura, Y.; Shida, Y.; Kasai, M.; Ashizawa, T.; Gomi, K. U.S. Patent 5220026, 1993; Eur. Patent 487097A1, 1992; Chem. Abstr. 1992, 117, 90167.
4. Ashizawa, T.; Shimizu, M.; Gomi, K.; Okabe, M. Anti-Cancer Drugs 1998, 9, 263.
5. Sugaya, T.; Mimura, Y.; Kato, N.; Ikuta, M.; Mimura, T.; Kasai, M.; Tomioka, S. Synthesis 1994, 73.
6. Kato, N.; Sugaya, T.; Mimura, T.; Ikuta, M.; Kato, S.; Kuge, Y.; Tomioka, S.; Kasai, M. Synthesis 1997, 625.
7. 2O=6/1, pH 2.7 adjusted with 85% phosphoric acid; flow rate: 1.0 mL/min; detection: UV 254 nm.
8. 3. This method was too diluted and very inefficient for the production, so a new efficient reducing method was required.
9. Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560.
10. HPLC analysis conditions; column: YMC pack AM-312 ODS 6 × 150 mm; mobile phase: MeCN/phosphate buffer (0.1 mol/ L, pH 2.7)=70/30 and sodium 1-octanesufonate (0.01 mol/L); flow rate: 1.0 mL/min; detection: UV 254 nm.
11. HPLC analysis conditions; column: YMC pack AM-312 ODS 6 × 150 mm; mobile phase; MeCN/phosphate buffer (0.1 mol/ L, pH 2.7)=35/65 and sodium 1-octanesufonate (0.01 mol/L); flow rate: 1.0 mL/min; detection: UV 254 nm.
12. HPLC analysis conditions; column: YMC pack AM-312 ODS 6 × 150 mm; mobile phase: MeCN/phosphate buffer (0.1 mol/ L, pH 2.7)=30/70 and sodium 1-octanesufonate (0.01 mol/L); flow rate: 1.0 mL/min; detection: UV 254 nm.
13. Kovendi, A.; Kiricz, M. Chem. Ber. 1964, 97, 1896.
14. Wakogel-200 was commercially available silica gel from Wako Chemical Co.