39026-92-1

Basic information

• Product Name: (4S)-4-Ethyl-4-hydroxy-10-methoxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
• Synonyms: (4S)-10-Methoxy-4α-ethyl-4β-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione;(4S)-4-Ethyl-4-hydroxy-10-methoxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione;(4S)-4α-Ethyl-4-hydroxy-10-methoxy-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione;11-Methoxycamptothecin;Methoxycamptothecin, 9-
• CAS NO: 39026-92-1
• Molecular Formula: C₂₁H₁₈N₂O₅
• Molecular Weight: 378.378
• Product Categories: Alkaloids
• Mol File: 39026-92-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 223-225℃
• Boiling Point: 773.1 °C at 760 mmHg
• Flash Point: 421.4 °C
• Appearance: /
• Density: 1.50±0.1 g/cm3 (20 ºC 760 Torr)
• PKA: 11.20±0.20(Predicted)
• CAS DataBase Reference: (4S)-4-Ethyl-4-hydroxy-10-methoxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (4S)-4-Ethyl-4-hydroxy-10-methoxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione(39026-92-1)
• EPA Substance Registry System: (4S)-4-Ethyl-4-hydroxy-10-methoxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione(39026-92-1)

Safety Data

• Hazardous Substances Data: 39026-92-1(Hazardous Substances Data)

Synthetic route

diazomethane (186581-53-3, 908094-01-9) + 10-hydroxycamptothecin (67656-30-8) → 9-methoxycamptothecin (39026-92-1)

Conditions	Yield
In 1,4-dioxane; methanol; diethyl ether for 1h; Ambient temperature;	95.5%
	94%

9-amino-20(S)-camptothecin (91421-43-1) → 9-methoxycamptothecin (39026-92-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 36 percent / aq. NaNO2; H2SO4 / Heating View Scheme
Multi-step reaction with 2 steps 1: 1.) 20percent aq. H2SO4, aq. NaNO2, 2.) H2O / 1.) 0-5 deg C, 15 min, 2.) reflux, 1 h 2: 95.5 percent / methanol; dioxane; diethyl ether / 1 h / Ambient temperature View Scheme

rubitecan (91421-42-0) → 9-methoxycamptothecin (39026-92-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 81 percent / SnCl2; Sn; aq. HCl 2: 36 percent / aq. NaNO2; H2SO4 / Heating View Scheme
Multi-step reaction with 3 steps 1: 95.2 percent / H2 / PtO2 / ethanol; dioxane / 2 h / 760 Torr 2: 1.) 20percent aq. H2SO4, aq. NaNO2, 2.) H2O / 1.) 0-5 deg C, 15 min, 2.) reflux, 1 h 3: 95.5 percent / methanol; dioxane; diethyl ether / 1 h / Ambient temperature View Scheme

camptothecin (7689-03-4) → 9-methoxycamptothecin (39026-92-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: 24 percent / aq. HNO3; H2SO4 2: 81 percent / SnCl2; Sn; aq. HCl 3: 36 percent / aq. NaNO2; H2SO4 / Heating View Scheme

20-O-acetyl-10-methoxycamptothecin + Camptothecin 1-oxide (86639-48-7) + (20S)-20-O-Acetylcamptothecin (7688-64-4) + 1,1,1-trichloro-2-methyl-2-propanol (57-15-8) → 9-methoxycamptothecin (39026-92-1)

Conditions	Yield
With pyridine; sulfuric acid; acetic anhydride In 1,4-dioxane; methanol

9-methoxycamptothecin (39026-92-1) → 7-ethyl-10-hydroxy-mappicine ketone (142727-51-3)

Conditions	Yield
for 0.116667h; Irradiation;	94%
In various solvent(s) at 200℃; for 9.5h;	79%
for 0.116667h; Irradiation;

acetic anhydride (108-24-7) + 9-methoxycamptothecin (39026-92-1) → 9-methoxycamptothecin acetate (39026-93-2)

Conditions	Yield
With lithium bromide at 20℃; for 24h;	62%

9-methoxycamptothecin (39026-92-1) → 9-methoxymappicine (142727-79-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 0.12 h / Irradiation 2: 91 percent / NaBH4 / methanol View Scheme
Multi-step reaction with 2 steps 1: 94 percent / 0.12 h / Irradiation 2: 90 percent / NaBH4 / methanol / 2 h / Ambient temperature View Scheme

9-methoxycamptothecin (39026-92-1) → (R)-9-methoxymappicine

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 0.12 h / Irradiation 2.1: NaBH4 / methanol 2.2: Candida cylindracea lipase; vinyl acetate / CHCl3 / 168 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1: 94 percent / 0.12 h / Irradiation 2: 90 percent / NaBH4 / methanol / 2 h / Ambient temperature 3: 82 percent / pyridine / Ambient temperature 4: 45 percent / lipase Amano PS (Pseudomonas cepacia), phosphate buffer / tetrahydrofuran / 72 h View Scheme
Multi-step reaction with 5 steps 1: 94 percent / 0.12 h / Irradiation 2: 90 percent / NaBH4 / methanol / 2 h / Ambient temperature 3: 82 percent / pyridine / Ambient temperature 4: 47 percent / Baker's yeast (Saccharomyces cerevisiae), sucrose / H2O / 192 h / Ambient temperature 5: 98 percent / 10 percent aq. K2CO3 / methanol / 2 h / Heating View Scheme

9-methoxycamptothecin (39026-92-1) → (S)-9-methoxymappicine (243846-86-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: 0.12 h / Irradiation 2: 91 percent / NaBH4 / methanol 3: Candida cylindracea lioase / CHCl3 / 168 h / 20 °C 4: 10 percent aq. K2CO3 / methanol / 2 h / Heating View Scheme
Multi-step reaction with 2 steps 1.1: 0.12 h / Irradiation 2.1: NaBH4 / methanol 2.2: Candida cylindracea lipase; vinyl acetate / CHCl3 / 168 h / 20 °C View Scheme
Multi-step reaction with 5 steps 1: 94 percent / 0.12 h / Irradiation 2: 90 percent / NaBH4 / methanol / 2 h / Ambient temperature 3: 82 percent / pyridine / Ambient temperature 4: 45 percent / lipase Amano PS (Pseudomonas cepacia), phosphate buffer / tetrahydrofuran / 72 h 5: 96 percent / 10 percent aq.K2CO3 / methanol / 2 h / Heating View Scheme
Multi-step reaction with 4 steps 1: 94 percent / 0.12 h / Irradiation 2: 90 percent / NaBH4 / methanol / 2 h / Ambient temperature 3: 82 percent / pyridine / Ambient temperature 4: 47 percent / Baker's yeast (Saccharomyces cerevisiae), sucrose / H2O / 192 h / Ambient temperature View Scheme

9-methoxycamptothecin (39026-92-1) → (S)-9-methoxymappicine acetate (243846-92-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 0.12 h / Irradiation 2: 91 percent / NaBH4 / methanol 3: Candida cylindracea lioase / CHCl3 / 168 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1: 94 percent / 0.12 h / Irradiation 2: 90 percent / NaBH4 / methanol / 2 h / Ambient temperature 3: 82 percent / pyridine / Ambient temperature 4: 45 percent / lipase Amano PS (Pseudomonas cepacia), phosphate buffer / tetrahydrofuran / 72 h View Scheme

9-methoxycamptothecin (39026-92-1) → acetic acid 1-(1-methoxy-8-methyl-9-oxo-9,11-dihydro-indolizino[1,2-b]quinolin-7-yl)-propyl ester (243846-91-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 0.12 h / Irradiation 2: 91 percent / NaBH4 / methanol 3: Candida cylindracea lioase / CHCl3 / 168 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1: 94 percent / 0.12 h / Irradiation 2: 90 percent / NaBH4 / methanol / 2 h / Ambient temperature 3: 82 percent / pyridine / Ambient temperature 4: 47 percent / Baker's yeast (Saccharomyces cerevisiae), sucrose / H2O / 192 h / Ambient temperature View Scheme

9-methoxycamptothecin (39026-92-1) → acetic acid 1-(1-methoxy-8-methyl-9-oxo-9,11-dihydro-indolizino[1,2-b]quinolin-7-yl)-propyl ester (243846-90-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 94 percent / 0.12 h / Irradiation 2: 90 percent / NaBH4 / methanol / 2 h / Ambient temperature 3: 82 percent / pyridine / Ambient temperature View Scheme

ethanol (64-17-5) + 9-methoxycamptothecin (39026-92-1) → 5-ethoxy-9-methoxycamptothecin (200618-95-7)

Conditions	Yield
With cerium(IV)diammonium nitrate In dichloromethane at 20℃; for 2h;
With ammonium cerium(IV) nitrate In dichloromethane at 20℃; for 2h;

acetic acid (64-19-7) + 9-methoxycamptothecin (39026-92-1) → 5-acetoxy-9-methoxycamptothecin (714251-44-2)

Conditions	Yield
With cerium(IV)diammonium nitrate at 20℃; for 8h;
With ammonium cerium(IV) nitrate at 20℃; for 8h;

9-methoxycamptothecin (39026-92-1) → 5-ethoxy-9-methoxycamptothecin (200618-95-7)

Conditions	Yield
With sulfuric acid; iron(III) chloride In ethanol

Upstream product

• 86639-48-7 Camptothecin 1-oxide 
• 7688-64-4 (20S)-20-O-Acetylcamptothecin 
• 57-15-8 1,1,1-trichloro-2-methyl-2-propanol 
• 7689-03-4 camptothecin 
• 91421-42-0 rubitecan 
• 91421-43-1 9-amino-20(S)-camptothecin 
• 186581-53-3 diazomethane 
• 67656-30-8 10-hydroxycamptothecin 

Downstream Products

• 67656-30-8 10-hydroxycamptothecin 

Relevant articles and documents

Radiosynthesis of carbon-11-labeled camptothecin derivatives as potential positron emission tomography tracers for imaging of topoisomerase I in cancers

Four carbon-11-labeled camptothecin derivatives, 9-[11C]methoxy- 20(S)-camptothecin ([11C]5), 10-[11C]methoxy-20(S)- camptothecin ([11C]7), 9-nitro-10-[11C]methoxy-20(S)- camptothecin ([11C]9), and 9-[([11C]trimethylamino)methyl] -10-hydroxy-20(S)-camptothecin ([11C]11), have been synthesized as potential positron emission tomography tracers for imaging of topoisomerase I in cancers.

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

20(S)-Camptothecin derivatives having nitro, amino, chloro, bromo, hydroxyl and methoxyl groups in the A-ring were synthesized. B-Ring hydrogenated camptothecin (2a) was converted into 10-hydroxycamptothecin (6e) by treatment with lead tetraacetate in trifluoroacetic acid. 10-Substituted derivatives (6) were obtained by a photoreaction of N-oxides (9). The cytotoxicity of the A-ring modified camptothecins was evaluated against KB cells in vitro and leukemia L1210 in mice. 7-Ethyl-10-hydroxycamptothecin (6i) was identified as a potential derivative for further modification.