e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Synthesis and antitumor activity of 20 (S)-camptothecin derivatives: A-ring modified and 7, 10-disubstituted camptothecins.

沢田誠吾，松岡俊一，野方健一郎，永田洋…

Index: Chemical and Pharmaceutical Bulletin, , vol. 39, # 12 p. 3183 - 3188

Full Text: HTML

Citation Number: 93

Abstract

... Yaho 1796, Kunitachi—shi, Tokyo 186, Japan and School of Pharmaceutical Sciences, Showa ... in 1966.2“) A-Ring substituted camptothecins were obtained by chemical modiﬁcations of ... Chemistry A-Ring modiﬁed 20(S)-camptothecins were obtained starting from corresponding ...

Campathecin Structure

~31%

rubitecan Structure

12-nitro-(20S)-camptothecin Structure

12-nitro-(20S)-...

7-Ethylcamptothecin Structure

7-Ethylcamptothecin

~%

7-Ethyl-10-hydroxycamptothecin Structure

7-Ethyl-10-hydr...

7-Ethylcamptothecin 1-Oxide Structure

7-Ethylcamptoth...

~48%

7-Ethyl-10-hydroxycamptothecin Structure

7-Ethyl-10-hydr...

7-ethyl-12-hydroxycamptothecin Structure

7-ethyl-12-hydr...

Camptothecin N-oxide Structure

Camptothecin N-oxide

~%

(4S)-4-Ethyl-4-hydroxy-9-methoxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione Structure

(4S)-4-Ethyl-4-...

4-ethyl-4-hydroxy-1,5b,6,11,11a,12-hexahydro-4H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione Structure

4-ethyl-4-hydro...

~%

(4S)-4-Ethyl-4-hydroxy-9-methoxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione Structure

(4S)-4-Ethyl-4-...

9-Nitrocamptothecin Structure

9-Nitrocamptothecin

~%

(4S)-4-Ethyl-4-hydroxy-9-methoxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione Structure

(4S)-4-Ethyl-4-...

(4R,5bS,11aS)-4-ethyl-4-hydroxy-9-nitro-1,5b,6,11,11a,12-hexahydro-14H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H)-dione Structure

(4R,5bS,11aS)-4...

~%

(4S)-4-Ethyl-4-hydroxy-9-methoxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione Structure

(4S)-4-Ethyl-4-...

Methanol Structure

Camptothecin N-oxide Structure

Camptothecin N-oxide

~39%

(S)-10-Hydroxycamptothecin Structure

(S)-10-Hydroxyc...

(4S)-4-Ethyl-4-hydroxy-9-methoxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione Structure

(4S)-4-Ethyl-4-...

9-amino-20-camptothecin Structure

9-amino-20-camp...

~%

(4S)-4-Ethyl-4-hydroxy-9-methoxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione Structure

(4S)-4-Ethyl-4-...

Camptothecin N-oxide Structure

Camptothecin N-oxide

~12%

(S)-10-Hydroxycamptothecin Structure

(S)-10-Hydroxyc...

Campathecin Structure

acetic acid Structure

4-ethyl-4-hydroxy-1,5b,6,11,11a,12-hexahydro-4H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione Structure

4-ethyl-4-hydro...

~9%

(S)-10-Hydroxycamptothecin Structure

(S)-10-Hydroxyc...

N/A Structure

Detail

4-ethyl-4-hydroxy-1,5b,6,11,11a,12-hexahydro-4H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione Structure

4-ethyl-4-hydro...

~12%

(S)-10-Hydroxycamptothecin Structure

(S)-10-Hydroxyc...

Campathecin Structure

4-ethyl-4-hydroxy-1,5b,6,11,11a,12-hexahydro-4H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione Structure

4-ethyl-4-hydro...

~%

(S)-10-Hydroxycamptothecin Structure

(S)-10-Hydroxyc...

Camptothecin N-oxide Structure

Camptothecin N-oxide

~%

(S)-10-Hydroxycamptothecin Structure

(S)-10-Hydroxyc...

Camptothecin N-oxide Structure

Camptothecin N-oxide

Ethylsulfanylacetat Structure

Ethylsulfanylacetat

~56%

(S)-10-Hydroxycamptothecin Structure

(S)-10-Hydroxyc...

ethyl (S)-2-((4-ethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl)thio)acetate Structure

ethyl (S)-2-((4...

9-Nitrocamptothecin Structure

9-Nitrocamptothecin

~%

(S)-10-Hydroxycamptothecin Structure

(S)-10-Hydroxyc...

(4R,5bS,11aS)-4-ethyl-4-hydroxy-9-nitro-1,5b,6,11,11a,12-hexahydro-14H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H)-dione Structure

(4R,5bS,11aS)-4...

~%

(S)-10-Hydroxycamptothecin Structure

(S)-10-Hydroxyc...

Camptothecin N-oxide Structure

Camptothecin N-oxide

acetic acid Structure

~25%

(S)-10-Hydroxycamptothecin Structure

(S)-10-Hydroxyc...

N/A Structure

Methanol Structure

Camptothecin N-oxide Structure

Camptothecin N-oxide

~22%

(S)-10-Hydroxycamptothecin Structure

(S)-10-Hydroxyc...

(4S)-4-Ethyl-4-hydroxy-9-methoxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione Structure

(4S)-4-Ethyl-4-...

Camptothecin N-oxide Structure

Camptothecin N-oxide

~77%

(S)-10-Hydroxycamptothecin Structure

(S)-10-Hydroxyc...

Campathecin Structure

acetic acid Structure

4-ethyl-4-hydroxy-1,5b,6,11,11a,12-hexahydro-4H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione Structure

4-ethyl-4-hydro...

~31%

(S)-10-Hydroxycamptothecin Structure

(S)-10-Hydroxyc...

N/A Structure

Detail

4-ethyl-4-hydroxy-1,5b,6,11,11a,12-hexahydro-4H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione Structure

4-ethyl-4-hydro...

~75%

(S)-10-Hydroxycamptothecin Structure

(S)-10-Hydroxyc...

Campathecin Structure

9-amino-20-camptothecin Structure

9-amino-20-camp...

~%

(S)-10-Hydroxycamptothecin Structure

(S)-10-Hydroxyc...

Camptothecin N-oxide Structure

Camptothecin N-oxide

~%

9-Nitrocamptothecin Structure

9-Nitrocamptothecin

Campathecin Structure

~%

9-Nitrocamptothecin Structure

9-Nitrocamptothecin

(4R,5bS,11aS)-4-ethyl-4-hydroxy-9-nitro-1,5b,6,11,11a,12-hexahydro-14H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H)-dione Structure

(4R,5bS,11aS)-4...

~%

9-Nitrocamptothecin Structure

9-Nitrocamptothecin

4-ethyl-4-hydroxy-1,5b,6,11,11a,12-hexahydro-4H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione Structure

4-ethyl-4-hydro...

~%

9-Nitrocamptothecin Structure

9-Nitrocamptothecin

Camptothecin N-oxide Structure

Camptothecin N-oxide

~%

9-amino-20-camptothecin Structure

9-amino-20-camp...

4-ethyl-4-hydroxy-1,5b,6,11,11a,12-hexahydro-4H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione Structure

4-ethyl-4-hydro...

~%

9-amino-20-camptothecin Structure

9-amino-20-camp...

(4R,5bS,11aS)-4-ethyl-4-hydroxy-9-nitro-1,5b,6,11,11a,12-hexahydro-14H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H)-dione Structure

(4R,5bS,11aS)-4...

~%

9-amino-20-camptothecin Structure

9-amino-20-camp...

Campathecin Structure

~%

9-amino-20-camptothecin Structure

9-amino-20-camp...

Radiosynthesis of carbon-11-labeled camptothecin derivatives...

[Gao, Mingzhang; Miller, Kathy D.; Sledge, George W.; Zheng, Qi-Huang Bioorganic and Medicinal Chemistry Letters, 2005 , vol. 15, # 17 p. 3865 - 3869]

A practical regiospecific synthesis of 9-nitrocamptothecin

[Synthesis, , # 12 p. 1940 - 1942]

A practical regiospecific synthesis of 9-nitrocamptothecin

[Synthesis, , # 12 p. 1940 - 1942]

A practical regiospecific synthesis of 9-nitrocamptothecin

[Synthesis, , # 12 p. 1940 - 1942]

Plant antitumor agents. 30. Synthesis and structure activity...

[Wall, Monroe E.; Wani, Mansukh C.; Nicholas, Allan W.; Manikumar, Govindarajan; Tele, Chhagan; et al. Journal of Medicinal Chemistry, 1993 , vol. 36, # 18 p. 2689 - 2700]