(+)-Camptothecin supplier | CasNO.7689-03-4

Name
(+)-Camptothecin
EINECS 444-280-6
CAS No. 7689-03-4
Article Data78
CAS DataBase
Density 1.513 g/cm³
Solubility insoluble in water
Melting Point 260 °C (dec.)(lit.)
Formula C₂₀H₁₆N₂O₄
Boiling Point 757.01 °C at 760 mmHg
Molecular Weight 348.358
Flash Point 411.625 °C
Transport Information UN 1544 6.1/PG 3
Appearance light yellow crystal powder
Safety 45-36/37/39-26
Risk Codes 36/37/38-25-20/21/22
Molecular Structure
Hazard Symbols T, Xn, Xi
Synonyms (S)-(+)-Camptothecin;Camptothecin;Camptothecinum;Campthecin;Camptothecine;4(S)-Ethyl-4-hydroxy-1H-pyrano-[3',4':6,7]indolizino[1,2-b]quinoline-3,14 (4H,12H)-dione;Camptothecine(CPT);
PSA 81.42000
LogP 2.07960

Synthetic route

: 1085755-35-6
C29H39N3O3Si2

: 7689-03-4
camptothecin

Conditions

Conditions	Yield
With hydrogenchloride In diethyl ether; ethanol Pinner reaction; Heating;	92%

: 935761-84-5
camptothecin 20-(2-bromo)-n-butyrate

: 7689-03-4
camptothecin

Conditions

Conditions	Yield
With methanol; ammonia In tetrahydrofuran for 12h; Product distribution / selectivity;	89%

: 55857-35-7
(E)-N-(2-aminobenzylidene)-4-methylaniline

: 110351-94-5
(4S)-4-ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione

: 7689-03-4
camptothecin

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene Heating; 1) 30 min, 2) 3 h;	84.4%
With toluene-4-sulfonic acid In toluene Heating; 1.) 30 min, 2.) 3 h with Dean-Stark trap;	84%
With toluene-4-sulfonic acid In toluene	73%
With toluene-4-sulfonic acid 1.) toluene, reflux, 30 min, 2.) toluene, reflux, 3 h; Yield given. Multistep reaction;

: 841276-70-8
4-ethyl-1,12-dihydro-14H-pyrano[3',4':6,7indolizino[1,2-b]]quinolin-14-one

: 7689-03-4
camptothecin

Conditions

Conditions	Yield
Stage #1: 4-ethyl-1,12-dihydro-14H-pyrano[3',4':6,7indolizino[1,2-b]]quinolin-14-one With potassium osmate; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III) In water; tert-butyl alcohol at 0℃; Stage #2: With iodine; calcium carbonate In methanol; water at 40℃;	83%
Multi-step reaction with 2 steps 1: K2CO3; MeSO2NH2; K3Fe(CN)6 / OsO4; (DHQD)2-Py / 2-methyl-propan-2-ol; H2O / 7 h / 0 °C 2: I2; CaCO3 / methanol; H2O / 24 h / 20 °C View Scheme
With methanol; iodine; calcium carbonate In water Sharpless Dihydroxylation;
Multi-step reaction with 2 steps 1: potassium carbonate; hydroquinidine (2,5-diphenyl-4,6-pyrimidinediyl) diether; potassium hexacyanoferrate(III); potassium osmate(VI) dihydrate; methanesulfonamide / water; tert-butyl alcohol / 72 h / 0 °C / Inert atmosphere 2: iodine; calcium carbonate / methanol; water / 20 h / 40 °C / Inert atmosphere View Scheme

: 916236-87-8
(S)-O-methylcamptothecin

: 7689-03-4
camptothecin

Conditions

Conditions	Yield
With hydrogen bromide for 0.416667h; Heating;	81%

PHF-succinate: PHF-succinate

: 20-O-(glycyl)camptothecin trifluoroacetic acid salt

A: 672333-51-6
camptothecin-20-(N-succinamidoglycinate)

B camptothecin-PHF conjugate: camptothecin-PHF conjugate

C: 847928-87-4
camptothecin-20-(N-succinimidoglycinate)

D: 7689-03-4
camptothecin

Conditions

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In water; N,N-dimethyl-formamide; acetonitrile at -2 - 20℃; for 3.5h; pH=5.9 - 6.0;	A n/a B 80% C n/a D n/a

...Expand

: 50-00-0
formaldehyd

: 7-((2R,4S)-2-tert-butyl-4-ethyl-5-oxo-1,3-dioxolan-4-yl)indolizino[1,2-b]quinolin-9(11H)-one

: 7689-03-4
camptothecin

Conditions

Conditions	Yield
With hydrogenchloride; acetic acid In 1,4-dioxane; water at 90℃; for 19h;	80%

: 110351-94-5
(4S)-4-ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione

: 529-23-7
2-aminobenzaldehyde

: 7689-03-4
camptothecin

Conditions

Conditions	Yield
With chloro-trimethyl-silane In N,N-dimethyl-formamide at 100℃; Friedlaender Quinoline Synthesis;	78%
With toluene-4-sulfonic acid In toluene for 2h; Heating;	57%

: 86639-48-7
Camptothecin 1-oxide

A: 19685-09-7
(S)-10-hydroxycamptothecin

B: 7689-03-4
camptothecin

Conditions

Conditions	Yield
With sulfuric acid In 1,4-dioxane for 0.5h; Irradiation;	A 75% B 11.5%

: 53544-22-2, 142696-57-9, 142696-58-0
1,2,6,7-tetrahydrocamptothecin

A: 19685-09-7
(S)-10-hydroxycamptothecin

B: 7689-03-4
camptothecin

Conditions

Conditions	Yield
With lead(IV) acetate; trifluoroacetic acid for 0.25h; Ambient temperature;	A 73.5% B 12%

: 1197040-29-1
phenyl isocyanate

: 174092-80-9
(S)-4-ethyl-4-hydroxy-6-iodo-7-(prop-2-yn-1-yl)-1,7-dihydro-3H-pyrano[3,4-c]pyridino-3,8(4H)-dione

: 7689-03-4
camptothecin

Conditions

Conditions	Yield
With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; potassium carbonate; triethylamine In acetonitrile at 20℃; for 24h; Inert atmosphere; Schlenk technique; Irradiation;	73%
With hexamethyldistannane In benzene at 70℃; for 5h; Irradiation;	63%
With hexamethyldistannane In benzene	21.8 mg (63%)

: 935761-80-1
camptothecin 20-(4-bromo)-n-butyrate

: 7689-03-4
camptothecin

Conditions

Conditions	Yield
With methanol; ammonia In tetrahydrofuran for 12h; Product distribution / selectivity;	72%

: 841276-70-8
4-ethyl-1,12-dihydro-14H-pyrano[3',4':6,7indolizino[1,2-b]]quinolin-14-one

A: 110351-92-3
(R)-4-ethyl-4-hydroxy-1,12-dihydro-14H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-(4H)-dione

B: 7689-03-4
camptothecin

Conditions

Conditions	Yield
Stage #1: 4-ethyl-1,12-dihydro-14H-pyrano[3',4':6,7indolizino[1,2-b]]quinolin-14-one With methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III); hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; potassium dioxotetrahydroxoosmate(VI) In water; tert-butyl alcohol at 0℃; for 40h; Sharpless dihydroxylation; Stage #2: With iodine; calcium carbonate In methanol; water at 40℃; for 15h; Further stages.;	A n/a B 71%

Yield

Stage #1: 4-ethyl-1,12-dihydro-14H-pyrano[3',4':6,7indolizino[1,2-b]]quinolin-14-one With methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III); hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; potassium dioxotetrahydroxoosmate(VI) In water; tert-butyl alcohol at 0℃; for 40h; Sharpless dihydroxylation;
Stage #2: With iodine; calcium carbonate In methanol; water at 40℃; for 15h; Further stages.;

A n/a
B 71%

: 26908-34-9
N-(2-(1,3-dioxolan-2-yl))phenylamine

: 110351-94-5
(4S)-4-ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione

: 7689-03-4
camptothecin

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 3h; Heating;	69%

: 26908-34-9
N-(2-(1,3-dioxolan-2-yl))phenylamine

: 102978-41-6
4'-ethyl-1',4',7',8'-tetrahydro-4'-hydroxy-3'H,10'H-spiro[1,3-dioxolane-2,6'-pyrano[3,4-f]indolizine]-3',10'-dione

: 7689-03-4
camptothecin

Conditions

Conditions	Yield
With hydrogenchloride In ethanol; water for 4h; Friedlaender synthesis; Reflux;	66%

: 390824-47-2
(S)-7-[(2-chloroquinolin-3-yl)methyl]-4-ethyl-4-hydroxy-1Hpyrano[3,4-c]pyridine-3,8(4H,7H)-dione

: 7689-03-4
camptothecin

Conditions

Conditions	Yield
With bis(triphenylphosphine) palladium (Il) acetate; potassium acetate In acetonitrile at 100℃; for 12h; Heck reaction;	64%
With bis(acetato)bis(triphenylphosphine)palladium(0); potassium acetate In acetonitrile at 100℃; for 12h; Heck reaction; Inert atmosphere; optical yield given as %ee;	64%

: 91421-43-1
9-amino-20(S)-camptothecin

A: 67656-30-8
10-hydroxycamptothecin

B: 7689-03-4
camptothecin

Conditions

Conditions	Yield
With sulfuric acid; sodium nitrite In water for 1h; Heating;	A 60% B n/a

: 210563-62-5
(-)-O,21-dihydrocamptothecin

: 7689-03-4
camptothecin

Conditions

Conditions	Yield
With iodine; calcium carbonate In methanol; water at 20℃; for 96h;	60%
With iodine; calcium carbonate In methanol; water at 40℃; for 24h; Inert atmosphere; optical yield given as %ee;
With iodine; calcium carbonate In methanol; water at 40℃; for 20h; Inert atmosphere;	59 mg

: 29681-57-0
tert-butyldimethylsilane

: 86639-48-7
Camptothecin 1-oxide

A: 7689-03-4
camptothecin

B: 203173-70-0
(20S)-7-tert-butyldimethylsilylcamptothecin

C: (20S)-12-tert-butyldimethylsilylcamptothecin

Conditions

Conditions	Yield
With di-tert-butyl peroxide; triisopropylsilanethiol	A 60% B 20% C n/a

...Expand

: 146596-04-5
(S)-7-(2-Bromo-quinolin-3-ylmethyl)-4-ethyl-4-hydroxy-1,7-dihydro-4H-pyrano[3,4-c]pyridine-3,8-dione

: 7689-03-4
camptothecin

Conditions

Conditions	Yield
With palladium diacetate; tetrabutylammomium bromide; potassium acetate In N,N-dimethyl-formamide at 90℃; for 3h;	59%
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In toluene Heating;	55%
With palladium diacetate; potassium carbonate; triphenylphosphine In toluene for 16h; Heck reaction; Reflux; Inert atmosphere;

: 935761-81-2
camptothecin 20-(5-bromo)-n-pentanoate

: 7689-03-4
camptothecin

Conditions

Conditions	Yield
With methanol; ammonia In tetrahydrofuran for 120h; Product distribution / selectivity;	59%

: 34141-35-0
4-ethyl-1,12-dihydro-14-H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-(4H)-dione

: 7689-03-4
camptothecin

Conditions

Conditions	Yield
Stage #1: 4-ethyl-1,12-dihydro-14-H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-(4H)-dione With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h; enolization; Stage #2: With (+)-(2S,8aS)-(camphorylsulfonyl)oxaziridine In tetrahydrofuran at -78℃; for 3h; Substitution; asymmetric hydroxylation;	53%

: 72594-33-3
(S)-4-ethyl-4-hexanoyloxy-1,12-dihydro-4H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione

: 7689-03-4
camptothecin

Conditions

Conditions	Yield
With methanol; ammonia In tetrahydrofuran for 120h; Product distribution / selectivity;	42%

: 64-19-7
acetic acid

: 53544-22-2, 142696-57-9, 142696-58-0
1,2,6,7-tetrahydrocamptothecin

A: 19685-09-7
(S)-10-hydroxycamptothecin

B: 19685-11-1
(S)-9-acetoxy-4-ethyl-4-hydroxy-1,12-dihydro-4H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione

C: 7689-03-4
camptothecin

Conditions

Conditions	Yield
With lead(IV) acetate for 0.25h; Ambient temperature;	A 30.9% B 20.8% C 8.1%

...Expand

: 1197040-29-1
phenyl isocyanate

: 202745-20-8
(S)-4-Ethyl-4-hydroxy-6-iodo-3-oxo-7-allyl-1H-pyrano[3,4-c]-8-pyridone

: 7689-03-4
camptothecin

Conditions

Conditions	Yield
With hexamethyldistannane In benzene Irradiation;	21%

: 69203-72-1
camptothecin-21-isopropylamide

A: 7689-03-4
camptothecin

B: 118514-62-8
N-Isopropyl-17-hydroxycamptothecin Lactam

C: 118514-63-9
N-Isopropyl-17-oxocamptothecin Lactam

Conditions

Conditions	Yield
With manganese(IV) oxide In dichloromethane for 72h; Ambient temperature;	A 3.4% B 8.1% C 12%

...Expand

: 56581-35-2
camtothecin-20-O-methyl carbonate

: 7689-03-4
camptothecin

Conditions

Conditions	Yield
With lithium hydrogensulfide In N,N,N,N,N,N-hexamethylphosphoric triamide

: 18,19-dehydrocamptothecin

: 7689-03-4
camptothecin

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol for 0.333333h; Ambient temperature;
With hydrogen; palladium 10% on activated carbon In 1,4-dioxane; methanol at 20℃; for 1 - 5h;

: 34079-22-6
camptothecin

: 7689-03-4
camptothecin

Conditions

Conditions	Yield
With Britton-Robinson's buffer pH 6.0; water at 37℃; Equilibrium constant; Kinetics; Thermodynamic data; Ea, A, var. pH, var. temp., var. time;
With PBS buffer at 37℃; pH=7.4; Kinetics;

: 30379-55-6
benzyloxyacetic acid

: 7689-03-4
camptothecin

: Benzyloxy-acetic acid (S)-4-ethyl-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-4-yl ester

Conditions

Conditions	Yield
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; for 12h;	100%
With dmap In dichloromethane for 12h;	100%
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; for 12h;	100%
With dmap; bis-2-propyl carbonate In dichloromethane at 0℃; for 3h;	65%

: 142955-50-8
N-(tert-butoxycarbonyl)-glycine N-carboxyanhydride

: 7689-03-4
camptothecin

: 204133-72-2
camptothecin N-tert-butyoxylcarboxylglycine ester

Conditions

Conditions	Yield
With dmap In dichloromethane for 8h; Heating;	100%

: 7689-03-4
camptothecin

: 25387-67-1
20(S)-camptothecin sodium salt

Conditions

Conditions	Yield
With sodium hydroxide; water at 50℃; for 1h;	100%
With sodium hydroxide; water at 50℃; for 2h;

: 123-62-6
propionic acid anhydride

: 7689-03-4
camptothecin

: 20-O-camptothecin propionate ester

Conditions

Conditions	Yield
sulfuric acid In ethanol at 80 - 120℃; for 14h;	99%
With pyridine at 40℃; for 48h;	94%
With pyridine at 35 - 45℃; for 48h;	94%

: 133498-97-2
t-BuOCO-Gly-Sar-OH

: 7689-03-4
camptothecin

: (tert-butoxycarbonylaminoacetyl-methyl-amino)-acetic acid (S)-4-ethyl-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-4-yl ester

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20 - 25℃; for 15h;	99%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 15h;	99%

: 7689-03-4
camptothecin

: 210563-62-5
(-)-O,21-dihydrocamptothecin

Conditions

Conditions	Yield
With potassium borohydride In methanol at 20℃; Inert atmosphere;	99%
With potassium borohydride In methanol at 20℃; for 1h;	98.4%
With sodium tetrahydroborate In methanol at 20℃;	90%

: 7689-03-4
camptothecin

: 401478-77-1
3-fluoro-4-cyanophenoxyacetic acid

: 401478-65-7
camptothecin-20-O-4-cyano-3-fluorophenoxyacetate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 20h;	98.7%

: 7689-03-4
camptothecin

: 598-78-7
(R,S)-2-chloropropionic acid

: 1112310-87-8
camptothecin-20-O-2-chloropropionate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2h;	98.1%

: 626-27-7
n-heptanoic anhydride

: 7689-03-4
camptothecin

: camptothecin-20-O-heptanoate

Conditions

Conditions	Yield
With pyridine at 40℃; for 48h;	98%
With pyridine	98%

: 994-30-9
triethylsilyl chloride

: 7689-03-4
camptothecin

: 1004264-93-0
20(S)-O-triethylsilylcamptothecin

Conditions

Conditions	Yield
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 20℃; for 60h;	98%
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	98%
With 1H-imidazole; dmap In N,N-dimethyl-formamide for 46h; Inert atmosphere;
Stage #1: camptothecin With 1H-imidazole In N,N-dimethyl-formamide for 0.166667h; Inert atmosphere; Stage #2: triethylsilyl chloride With dmap In N,N-dimethyl-formamide
With 1H-imidazole; dmap In N,N-dimethyl-formamide for 46.1667h;

: 108-30-5
succinic acid anhydride

: 7689-03-4
camptothecin

: 330155-39-0
(S)-4-((4-ethyl-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-4-yl)oxy)-4-oxobutanoic acid

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0 - 20℃; for 4h;	98%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0 - 20℃; for 4h; Inert atmosphere;	98%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane for 4h; Inert atmosphere; Cooling with ice;	90%

: 53308-95-5
N-tert-butoxycarbonyl-L-norvaline

: 7689-03-4
camptothecin

: 1204387-78-9
CPT-Nva-Boc

Conditions

Conditions	Yield
With dmap; diisopropyl-carbodiimide In dichloromethane at 0 - 20℃;	98%

: 6404-29-1
6-(tert-butoxycarbonylamino)hexanoic acid

: 7689-03-4
camptothecin

: (S)-4-ethyl-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3′,4′:6,7]indolizino[1,2-b]quinolin-4-yl 6-((tert-butoxycarbonyl)amino)hexanoate

Conditions

Conditions	Yield
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere;	98%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	98%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 25℃; for 12h;	55%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12h;	55%

: 3339-73-9
3-phthalimidopropanoic acid

: 7689-03-4
camptothecin

: 3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid 4-ethyl-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-4-yl ester

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 7h;	97.5%

: 79-11-8
chloroacetic acid

: 7689-03-4
camptothecin

: 7688-65-5
camptothecin-20-O-chloroacetate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2h;	97.5%

: 124-07-2
Octanoic acid

: 7689-03-4
camptothecin

: 10-octanoyloxy-7-ethylcamptothecin

Conditions

Conditions	Yield
With dmap; 2-chloro-1-methyl-pyridinium iodide In N,N-dimethyl acetamide at 50℃;	97.4%

: 79-08-3
bromoacetic acid

: 7689-03-4
camptothecin

: camptothecin-20 (S)-O-bromoacetate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2h;	97%
With dmap In dichloromethane for 5h; Cooling with ice;	71%
In dichloromethane for 5h; Cooling with ice;	71%
With dmap; bis-2-propyl carbonate In dichloromethane at 0℃; for 4h;	67%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2h;

: 84358-13-4
N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid

: 7689-03-4
camptothecin

: 1185274-90-1
Boc-Inp-CPT

Conditions

Conditions	Yield
Stage #1: N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 0.5h; Stage #2: camptothecin In dichloromethane at 20℃; for 18h;	97%

: 34306-42-8
Boc-Abu

: 7689-03-4
camptothecin

: 1204387-77-8
CPT-Abu-Boc

Conditions

Conditions	Yield
With dmap; diisopropyl-carbodiimide In dichloromethane at 0 - 20℃;	97%

: 7689-03-4
camptothecin

: 86639-48-7
Camptothecin 1-oxide

Conditions

Conditions	Yield
With sodium perborate; acetic acid at 30 - 90℃; for 0.833333h;	96.46%
With dihydrogen peroxide; acetic acid at 70 - 80℃; for 3.5h;	90.6%
With dihydrogen peroxide In acetic acid at 70 - 80℃; for 3.5h;	90.6%

: 75-91-2
tert.-butylhydroperoxide

: 7689-03-4
camptothecin

: 78287-26-0
(S)-7-methylcamptothecin

Conditions

Conditions	Yield
Stage #1: camptothecin With sulfuric acid; formamide; trifluoroacetic acid; iron(II) sulfate In water at 5℃; Stage #2: tert.-butylhydroperoxide In water at 0℃; for 1h;	96.1%
With sulfuric acid; iron(II) sulfate In water; acetic acid for 1h; Ambient temperature;	79%

: 7689-03-4
camptothecin

: 55854-89-2
8-methyl-7-propionylindolizino[1,2-b]quinoline-9(11H)-one

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate for 0.116667h; Ambient temperature; microwave irradiation;	96%
for 0.116667h; Irradiation;	96%
With sodium azide; 18-crown-6 ether In N,N-dimethyl-formamide at 110 - 120℃; for 18h; Mechanism;	94%

: 3744-87-4, 7764-95-6, 15761-38-3
Boc-(R)-Ala

: 7689-03-4
camptothecin

: (R)-2-tert-Butoxycarbonylamino-propionic acid (S)-4-ethyl-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-4-yl ester

Conditions

Conditions	Yield
With dmap; scandium tris(trifluoromethanesulfonate); diisopropyl-carbodiimide In dichloromethane at -8 - 20℃; for 2.5h;	96%

: 4530-20-5
BOC-glycine

: 7689-03-4
camptothecin

: 204133-72-2
camptothecin N-tert-butyoxylcarboxylglycine ester

Conditions

Conditions	Yield
With dmap; diisopropyl-carbodiimide In dichloromethane at 0 - 20℃;	96%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2h;	94.8%
With dmap; diisopropyl-carbodiimide In dichloromethane at 0℃; for 1h;	86.2%

: 123-38-6
propionaldehyde

: 7689-03-4
camptothecin

: 78287-27-1
7-ethylcamptothecin

Conditions

Conditions	Yield
With sulfuric acid; dihydrogen peroxide; acetic acid at -5 - 5℃; for 0.166667h; Temperature;	95.4%
With sulfuric acid; dihydrogen peroxide; iron(II) sulfate In water for 3h; Ambient temperature;	77%
With sulfuric acid; dihydrogen peroxide; iron(II) sulfate for 3h; Ambient temperature;	77%

: 7689-03-4
camptothecin

: 435270-82-9
3-[4-(4-fluorophenyl)-1-piperazinyl]propionic acid

: 3-[4-(4-fluoro-phenyl)-piperazin-1-yl]-propionic acid 4-ethyl-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-4-yl ester

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 7h;	95.2%

: 107-93-7
(E)-but-2-enoic acid

: 7689-03-4
camptothecin

: 194414-77-2
camptothecin-20-O-crotonate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane Ambient temperature;	95%

: 15761-38-3
L-N-Boc-Ala

: 7689-03-4
camptothecin

: 204133-34-6
20-O-(N-(tert-butoxycarbonyl)alanyl)camptothecin

Conditions

Conditions	Yield
With dmap; scandium tris(trifluoromethanesulfonate); diisopropyl-carbodiimide In dichloromethane at -8 - 20℃; for 2.5h;	95%
With dmap; diisopropyl-carbodiimide In dichloromethane at 0 - 20℃;	94%
With dmap; diisopropyl-carbodiimide In dichloromethane at 0℃; for 1h;	86.2%

: 140-10-3
(E)-3-phenylacrylic acid

: 7689-03-4
camptothecin

: (E)-3-Phenyl-acrylic acid (S)-4-ethyl-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-4-yl ester

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane Ambient temperature;	95%

: 913168-10-2
1H-benzo[d][1,2,3]triazol-1-yl (2-(pyridin-2-yldisulfaneyl)ethyl) carbonate

: 7689-03-4
camptothecin

: 914499-21-1
camptothecin-(4-pyridyldisulfanyl)ethyl carbonate

Conditions

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃;	95%

(+)-Camptothecin Chemical Properties

Following is the structure of Camptothecine (CAS NO.7689-03-4):

IUPAC Name: 4(S)-Ethyl-4-hydroxy-1H-pyrano-[3',4':6,7]indolizino[1,2-b]quinoline-3,14 (4H,12H)-dione
Molecular formula: C₂₀H₁₆N₂O₄
Molar mass: 348.35
EINECS: 444-280-6
Melting point: 260 °C
storage temp.: 2-8 °C
Index of Refraction: 1.746
Molar Refractivity: 93.44 cm³
Molar Volume: 230.2 cm³
Density: 1.51 g/cm³
Flash Point: 411.6 °C
Water Solubility: insoluble
Surface Tension: 80.1 dyne/cm
Enthalpy of Vaporization: 115.72 kJ/mol
Boiling Point: 757 °C at 760 mmHg
Vapour Pressure: 4.39E-24 mmHg at 25 °C
Appearance: Light yellow needle crystal
Solubility of Camptothecine (CAS NO.7689-03-4): chloroform/methanol (4:1): 4 mg/mL
Product Categories of Camptothecine (CAS NO.7689-03-4): Alkaloids; Antineoplastic; Camptothecin series; Antitumors for Research and Experimental Use; Biochemistry; Quinoline Alkaloids; Natural Plant Extract; Chiral Reagents; Heterocycles; Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals; Natural Anti-cancer Medical Materials and It's Derivatives; Antibiotics; Antibiotics A to; Antibiotics A-FAntibiotics; Antibiotics by Application; Antineoplastic and Immunosuppressive AntibioticsAntibiotics; Inhibits an EnzymeAntibiotics; Interferes with DNA Synthesis; Mechanism of Action;Antitumour; Signalling
Canonical SMILES: CCC1(C2=C(COC1=O)C(=O)N3CC4=CC5=CC=CC=C5N=C4C3=C2)O
Isomeric SMILES: CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=CC5=CC=CC=C5N=C4C3=C2)O
InChI: InChI=1S/C20H16N2O4/c1-2-20(25)14-8-16-17-12(7-11-5-3-4-6-15(11)21-17)9-22(16)18(23)13(14)10-26-19(20)24/h3-8,25H,2,9-10H2,1H3/t20-/m0/s1
InChIKey: VSJKWCGYPAHWDS-FQEVSTJZSA-N

(+)-Camptothecin Uses

Camptothecine (CAS NO.7689-03-4) is used as Antitumor alkaloid. Italso can be used in the treatment of stomach cancer, colon cancer,ect.

(+)-Camptothecin Toxicity Data With Reference

1.	dnd-omi 100 mg/L/30M	NATUAS Nature. 248 (1974),226.
2.	dnd-hmn:hla 20 µmol/L	CNREA8 Cancer Research. 33 (1973),2834.
3.	dni-hmn:hla 5 µmol/L	HXPHAU Handbuch der Experimentellen Pharmakologie. 38 (Pt 2),(1975),649.
4.	oms-hmn:hla 5 µmol/L	HXPHAU Handbuch der Experimentellen Pharmakologie. 38 (Pt 2),(1975),649.
5.	oms-mus:lym 1 mg/L	BCPCA6 Biochemical Pharmacology. 21 (1972),1977.
6.	dni-ckn:emb 500 µg/L	CJBIAE Canadian Journal of Biochemistry. 55 (1977),1180.
7.	ipr-mus LD50:64 mg/kg	CNREA8 Cancer Research. 39 (1979),2204.
8.	ivn-mus LD50:38 mg/kg	NCISP* National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program, Bethesda, MD 20205 JAN86 .

(+)-Camptothecin Safety Profile

Safety Information of Camptothecine (CAS NO.7689-03-4):
Hazard Codes: Toxic T, Irritant Xi, Harmful Xn
Risk Statements:36/37/38-25-20/21/22
36/37/38:Irritating to eyes, respiratory system and skin
25:Toxic if swallowed
20/21/22:Harmful by inhalation, in contact with skin and if swallowed
Safety Statements:45-36/37/39-26-36
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
36/37/39:Wear suitable protective clothing, gloves and eye/face protection
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:Wear suitable protective clothing
RIDADR:UN 1544 6.1/PG 3
WGK Germany:3
RTECS Note:UQ0492000
Hazard Note:Irritant
Poison by intravenous and intraperitoneal routes. Human mutation data reported. When heated to decomposition it emits toxic fumes of NO_x. See also CAMPTOTHECIN, SODIUM SALT.

(+)-Camptothecin Specification

Camptothecine , its cas register number is 7689-03-4. It also can be called (+)-Camptothecin ; 4-Ethyl-4-hydroxy-1H-pyrano-[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione .

Product Name

(+)-Camptothecin

Synthetic route

(+)-Camptothecin Chemical Properties

(+)-Camptothecin Uses

(+)-Camptothecin Toxicity Data With Reference

(+)-Camptothecin Safety Profile

(+)-Camptothecin Specification

Related Products

Hot Products