Welcome to LookChem.com Sign In|Join Free

CAS

  • or

19685-09-7 Suppliers

Post Buying Request

Recommended suppliersmore

  • Product
  • FOB Price
  • Min.Order
  • Supply Ability
  • Supplier
  • Contact Supplier
  • 19685-09-7 Structure
  • Basic information

    1. Product Name: 10-Hydroxycamptothecin
    2. Synonyms: Camptothecae Acuminatae extract;hydrate,(s)-dihydroxy;hydroxy-camptotheci;Hydroxycamptothencine;(20S)-10-HYDROXYCAMPTOTHECIN 98%;(20S)-10-Hydroxycamptothecin;HYDROCAMPTOTHECINE;CAMPTOTHECIN, 10-HYDROXY(SH)
    3. CAS NO:19685-09-7
    4. Molecular Formula: C20H16N2O5
    5. Molecular Weight: 364.35
    6. EINECS: 2017-001-1
    7. Product Categories: Inhibitors;Alkaloids;INTERMEDIATESOFIRINOTECANHCLTRIHYDRATE;Camptothecin series;Natural Plant Extract;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Natural Anti-cancer Medical Materials and It's Derivatives;natural product
    8. Mol File: 19685-09-7.mol
    9. Article Data: 22
  • Chemical Properties

    1. Melting Point: 265-270°C
    2. Boiling Point: 820.7 °C at 760 mmHg
    3. Flash Point: 450.1 °C
    4. Appearance: Yellow solid
    5. Density: 1.60
    6. Vapor Pressure: 1.67E-28mmHg at 25°C
    7. Refractive Index: 1.776
    8. Storage Temp.: -20°C Freezer
    9. Solubility: ≥23.8 mg/mL in DMSO with gentle warming; insoluble in EtOH; insoluble in H2O
    10. PKA: 8.93±0.40(Predicted)
    11. CAS DataBase Reference: 10-Hydroxycamptothecin(CAS DataBase Reference)
    12. NIST Chemistry Reference: 10-Hydroxycamptothecin(19685-09-7)
    13. EPA Substance Registry System: 10-Hydroxycamptothecin(19685-09-7)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: 24/25
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 19685-09-7(Hazardous Substances Data)

19685-09-7 Usage

Description

10-Hydroxycamptothecin, a derivative of Camptothecin, is a potent topoisomerase I inhibitor originally isolated from the Chinese tree Camptotheca acuminata. It is a yellow solid with strong anti-tumor activity against a wide range of experimental tumors, including L1210 leukemia cells. As a member of the camptothecin family, 10-Hydroxycamptothecin demonstrates less toxicity than its parent compound, making it a promising candidate for cancer therapy.

Uses

Used in Cancer Therapy:
10-Hydroxycamptothecin is used as a topoisomerase I inhibitor for cancer therapy. It targets the relaxation of DNA supercoiling by topoisomerase I at single-strand breaks, leading to the activation of apoptotic and cell cycle arrest pathways. This results in the inhibition of tumor growth and progression in various types of cancer.
Used in Pharmaceutical Industry:
10-Hydroxycamptothecin is used as an active pharmaceutical ingredient in the development of anticancer drugs. Its strong anti-tumor activity and less toxicity compared to the parent compound make it a valuable component in the formulation of cancer treatment medications.
Used in Research and Development:
10-Hydroxycamptothecin is used as a research compound in the study of topoisomerase I inhibitors and their potential applications in cancer therapy. It serves as a valuable tool for understanding the mechanisms of action and the development of novel anticancer agents.
Used in Drug Synthesis:
10-Hydroxycamptothecin is used as a key intermediate in the synthesis of various camptothecin-based anticancer drugs. Its unique chemical properties and strong anti-tumor activity make it an essential component in the development of new and effective cancer treatments.

in vitro

10-Hydroxycamptothecin inhibited the growth of BT-20 and MDA-231 cells with IC50 of 34.3nM and 7.27nM, respectively, which was more potent than camptothecin (CPT) with IC50>500nM. 10-Hydroxycamptothecin potently induces the formation of the pBR322 plasmid DNA cleavage complex mediated by human topoisomerase I with an EC50 of 0.35 μM, more than 50-fold more potent than CPT with an EC50 of 18.85 μM. 10-Hydroxycamptothecin treatment caused dose-dependent growth inhibition of human microvascular endothelial cells (HMECs) with IC50 of 0.31 μM and significantly inhibited HMEC migration with IC50 of 0.63 μM. Treatment of HMEC cells with 10-Hydroxycamptothecin also inhibited microtubule formation in a dose-dependent manner with IC50 of 0.96 μM. 10-Hydroxycamptothecin (5-20 nM) significantly inhibits the differentiation of Colo205 cells, arrests the cell cycle in G2 phase, and induces apoptosis through a caspase-3-dependent pathway.

in vivo

In the CAM model, 10-Hydroxycamptothecin treatment inhibited angiogenesis in a concentration-dependent manner, with 95% inhibition at 25 nM, more potent than suramin, which inhibited only 60% of angiogenesis at 125 nM. 10-Hydroxycamptothecin, administered orally at low doses of 2.5-7.5 mg/kg every two days, caused significant growth inhibition in Colo205 xenograft mice, but no acute toxicity. LD50: 104 mg/kg in mice (intraperitoneal injection).

IC 50

0.31 μm

references

[1] vladu b, woynarowski jm, manikumar g, wani mc, wall me, von hoff dd, wadkins rm. 7- and 10-substituted camptothecins: dependence of topoisomerase i-dna cleavable complex formation and stability on the 7- and 10-substituents. mol pharmacol. 2000 feb;57(2):243-51.[2] xiao d, tan w, li m, ding j. antiangiogenic potential of 10-hydroxycamptothecin. life sci. 2001 aug 24;69(14):1619-28. [3] ping yh, lee hc, lee jy, wu ph, ho lk, chi cw, lu mf, wang jj. anticancer effects of low-dose 10-hydroxycamptothecin in human colon cancer. oncol rep. 2006 may;15(5):1273-9.

Check Digit Verification of cas no

The CAS Registry Mumber 19685-09-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,9,6,8 and 5 respectively; the second part has 2 digits, 0 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 19685-09:
(7*1)+(6*9)+(5*6)+(4*8)+(3*5)+(2*0)+(1*9)=147
147 % 10 = 7
So 19685-09-7 is a valid CAS Registry Number.
InChI:InChI=1/C20H16N2O5/c1-2-20(26)14-7-16-17-11(5-10-6-12(23)3-4-15(10)21-17)8-22(16)18(24)13(14)9-27-19(20)25/h3-7,23,26H,2,8-9H2,1H3/t20-/m0/s1

19685-09-7 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • USP

  • (1347610)  Irinotecan Related Compound A  United States Pharmacopeia (USP) Reference Standard

  • 19685-09-7

  • 1347610-10MG

  • 14,578.20CNY

  • Detail

19685-09-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 10-Hydroxycamptothecin

1.2 Other means of identification

Product number -
Other names Hydroxycamptothecine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:19685-09-7 SDS

19685-09-7Synthetic route

camptothecin
7689-03-4

camptothecin

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

(S)-10-hydroxycamptothecin

Conditions
ConditionsYield
Stage #1: camptothecin With hydrogen; acetic acid; platinum(IV) oxide
Stage #2: With lead(IV) acetate; acetic acid
51%
Yield given. Multistep reaction;
With sulfuric acid; dihydrogen peroxide; acetic acid 2) irradiation; Yield given. Multistep reaction;
10-methoxycamptothecin
19685-10-0

10-methoxycamptothecin

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

(S)-10-hydroxycamptothecin

Conditions
ConditionsYield
With hydrogen bromide at 110℃; for 72h;82%
With hydrogen bromide In water at 110℃; for 7h; Inert atmosphere; optical yield given as %ee;80%
With hydrogen bromide In water at 100℃; Sealed tube;80%
With hydrogen bromide72%
With hydrogen bromide In water for 2h; Reflux;
camptothecin
7689-03-4

camptothecin

A

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

(S)-10-hydroxycamptothecin

B

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

Conditions
ConditionsYield
Stage #1: camptothecin With hydrogen; acetic acid; platinum under 760.051 Torr; for 8.5h;
Stage #2: With lead(IV) acetate In acetic acid Heating / reflux;
1,2,6,7-tetrahydro-(20S)-camphthotecine
870527-52-9

1,2,6,7-tetrahydro-(20S)-camphthotecine

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

(S)-10-hydroxycamptothecin

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene; water In acetic acid Yield given;
With [bis(acetoxy)iodo]benzene; acetic acid
In acetic acid at 20℃;
With [bis(acetoxy)iodo]benzene; acetic acid In water at 20℃; for 18h; Large scale reaction;1.36 kg
tetrahydrocamptothecin acetate

tetrahydrocamptothecin acetate

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

(S)-10-hydroxycamptothecin

Conditions
ConditionsYield
Stage #1: tetrahydrocamptothecin acetate With [bis(acetoxy)iodo]benzene In water; acetic acid at 27.5℃; for 18h;
Stage #2: With methanol In N,N-dimethyl-formamide at 27.5 - 76.5℃; for 6h;
10-hydroxycamptothecin

10-hydroxycamptothecin

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

(S)-10-hydroxycamptothecin

Conditions
ConditionsYield
In 1,4-dioxane; acetonitrile for 0.75h; UV-irradiation;98.5%
9-<(dimethylamino)methyl>-10-hydroxy-(20S)-camptothecin acetate salt
123948-88-9

9-<(dimethylamino)methyl>-10-hydroxy-(20S)-camptothecin acetate salt

A

(S)-10-[(dimethylamino)methyl]-4-ethyl-4,9-dihydroxy-12-methylene-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione
942429-91-6

(S)-10-[(dimethylamino)methyl]-4-ethyl-4,9-dihydroxy-12-methylene-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione

B

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

(S)-10-hydroxycamptothecin

C

Topotecan hydrochloride
119413-54-6, 123949-07-5

Topotecan hydrochloride

D

camptothecin
7689-03-4

camptothecin

Conditions
ConditionsYield
With hydrogenchloride In water for 0.25h;A < 0.04 %Chromat.
B < 0.001 %Chromat.
C 99.65 %Chromat.
D < 0.009 %Chromat.
1,2,6,7-tetrahydrocamptothecin
53544-22-2, 142696-57-9, 142696-58-0

1,2,6,7-tetrahydrocamptothecin

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

(S)-10-hydroxycamptothecin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 98 percent / pyridine / 1 h / 70 °C
2: 96.3 percent / H2SO4, conc. aq. HNO3 / 1 h
3: 82.3 percent / 20percent aq. H2SO4 / 2 h / Heating
4: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / dioxane / 2 h / Heating
5: 96.2 percent / H2 / PtO2 / ethanol; dioxane / 2 h / 760 Torr
6: 1.) 20percent aq. H2SO4, aq. NaNO2, 2.) H2O / 1.) 0-5 deg C, 15 min, 2.) reflux, 1 h
View Scheme
Multi-step reaction with 3 steps
1: 12 percent / Pb(OAc)4, trifluoroacetic acid / 0.25 h / Ambient temperature
2: 90.6 percent / 30percent aq. H2O2, acetic acid / 3.5 h / 70 - 80 °C
3: 22.5 percent / 1 N H2SO4 / dioxane / 0.5 h / Irradiation
View Scheme
Multi-step reaction with 3 steps
1: 12 percent / Pb(OAc)4, trifluoroacetic acid / 0.25 h / Ambient temperature
2: 90.6 percent / 30percent aq. H2O2, acetic acid / 3.5 h / 70 - 80 °C
3: 25 percent / 1 N aq. H2SO4 / dioxane / 0.5 h / Irradiation
View Scheme
Multi-step reaction with 3 steps
1: 12 percent / Pb(OAc)4, trifluoroacetic acid / 0.25 h / Ambient temperature
2: 90.6 percent / 30percent aq. H2O2, acetic acid / 3.5 h / 70 - 80 °C
3: 58 percent / 1 N aq. H2SO4 / dioxane / 0.5 h / Irradiation
View Scheme
2-[2,2-Dimethoxy-eth-(Z)-ylidene]-malonic acid benzyl ester methyl ester
161681-84-1

2-[2,2-Dimethoxy-eth-(Z)-ylidene]-malonic acid benzyl ester methyl ester

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

(S)-10-hydroxycamptothecin

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: LDA / tetrahydrofuran / -78 up to -20 deg C
2: H2 / 5percent Pd/C / methanol
3: 89 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, 1-hydroxybenzotriazole (HOBT), Et3N / tetrahydrofuran
4: TFA / H2O; toluene
5: DDQ
6: diisobutylaluminum hydride (DIBAH) / CH2Cl2
7: 1.) NaBH4; 2.) aq. NaOH / 1.) MeOH
8: 72 percent / 48percent HBr
View Scheme
Multi-step reaction with 8 steps
1: LDA / tetrahydrofuran / -78 up to -20 deg C
2: H2 / 5percent Pd/C / methanol
3: 89 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, 1-hydroxybenzotriazole (HOBT), Et3N / tetrahydrofuran
4: TFA / H2O; toluene
5: DDQ
6: diisobutylaluminum hydride (DIBAH) / CH2Cl2
7: NaBH4 / methanol
8: 72 percent / 48percent HBr
View Scheme
2-[1-((2R,4S)-2-tert-Butyl-4-ethyl-5-oxo-[1,3]dioxolan-4-yl)-2,2-dimethoxy-ethyl]-malonic acid benzyl ester methyl ester

2-[1-((2R,4S)-2-tert-Butyl-4-ethyl-5-oxo-[1,3]dioxolan-4-yl)-2,2-dimethoxy-ethyl]-malonic acid benzyl ester methyl ester

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

(S)-10-hydroxycamptothecin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: H2 / 5percent Pd/C / methanol
2: 89 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, 1-hydroxybenzotriazole (HOBT), Et3N / tetrahydrofuran
3: TFA / H2O; toluene
4: DDQ
5: diisobutylaluminum hydride (DIBAH) / CH2Cl2
6: 1.) NaBH4; 2.) aq. NaOH / 1.) MeOH
7: 72 percent / 48percent HBr
View Scheme
Multi-step reaction with 7 steps
1: H2 / 5percent Pd/C / methanol
2: 89 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, 1-hydroxybenzotriazole (HOBT), Et3N / tetrahydrofuran
3: TFA / H2O; toluene
4: DDQ
5: diisobutylaluminum hydride (DIBAH) / CH2Cl2
6: NaBH4 / methanol
7: 72 percent / 48percent HBr
View Scheme
(S)-4-ethyl-4-hydroxy-6-iodo-3-oxo-1H-pyrano[3,4-c]-8-pyridone
173442-34-7

(S)-4-ethyl-4-hydroxy-6-iodo-3-oxo-1H-pyrano[3,4-c]-8-pyridone

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

(S)-10-hydroxycamptothecin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 78 percent / NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide / 1.) 0 deg C, 10 min; r.t., 15 min, 2.) toluene, 70 deg C, 20 h
2: 51 percent / Me6Sn2 / benzene / 5 h / 70 °C / Irradiation
3: 82 percent / aq. HBr / 72 h / 110 °C
View Scheme
Multi-step reaction with 2 steps
1: 88 percent / NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide
2: Me3SnSnMe3 / benzene / 70 °C / Irradiation
View Scheme
(S)-4-ethyl-4-hydroxy-6-iodo-8-methoxy-1,4-dihydro-pyrano[3,4-c]pyridin-3-one
174092-79-6

(S)-4-ethyl-4-hydroxy-6-iodo-8-methoxy-1,4-dihydro-pyrano[3,4-c]pyridin-3-one

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

(S)-10-hydroxycamptothecin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 73 percent / Me3SiCl, NaI / acetonitrile; H2O / 5 h / 65 °C
2: 78 percent / NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide / 1.) 0 deg C, 10 min; r.t., 15 min, 2.) toluene, 70 deg C, 20 h
3: 51 percent / Me6Sn2 / benzene / 5 h / 70 °C / Irradiation
4: 82 percent / aq. HBr / 72 h / 110 °C
View Scheme
Multi-step reaction with 3 steps
1: 72 percent / aq. HI
2: 88 percent / NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide
3: Me3SnSnMe3 / benzene / 70 °C / Irradiation
View Scheme
Camptothecin 1-oxide
86639-48-7

Camptothecin 1-oxide

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

(S)-10-hydroxycamptothecin

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 11.5 percent / 1 N aq. H2SO4 / dioxane / 0.5 h / Irradiation
2: H2, acetic acid / PtO2 / dioxane / 760 Torr
3: 98 percent / pyridine / 1 h / 70 °C
4: 96.3 percent / H2SO4, conc. aq. HNO3 / 1 h
5: 82.3 percent / 20percent aq. H2SO4 / 2 h / Heating
6: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / dioxane / 2 h / Heating
7: 96.2 percent / H2 / PtO2 / ethanol; dioxane / 2 h / 760 Torr
8: 1.) 20percent aq. H2SO4, aq. NaNO2, 2.) H2O / 1.) 0-5 deg C, 15 min, 2.) reflux, 1 h
View Scheme
Multi-step reaction with 3 steps
1: 11.5 percent / 1 N aq. H2SO4 / dioxane / 0.5 h / Irradiation
2: H2, acetic acid / PtO2 / dioxane / 760 Torr
3: 73.5 percent / Pb(OAc)4, trifluoroacetic acid / 0.25 h / Ambient temperature
View Scheme
Camptothecin 1-oxide
86639-48-7

Camptothecin 1-oxide

A

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

(S)-10-hydroxycamptothecin

B

((S)-4-Ethyl-4-hydroxy-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-9-ylsulfanyl)-acetic acid ethyl ester
86639-49-8

((S)-4-Ethyl-4-hydroxy-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-9-ylsulfanyl)-acetic acid ethyl ester

Conditions
ConditionsYield
With sulfuric acid In 1,4-dioxane for 0.5h; Irradiation;A 58%
B 11.9%
10-nitro-(20S)-camptothecin
86639-62-5

10-nitro-(20S)-camptothecin

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

(S)-10-hydroxycamptothecin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 96.2 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
View Scheme
N,20-O-diacetyl-1,2,6,7-tetrahydrocamptothecin

N,20-O-diacetyl-1,2,6,7-tetrahydrocamptothecin

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

(S)-10-hydroxycamptothecin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 96.3 percent / H2SO4, conc. aq. HNO3 / 1 h
2: 82.3 percent / 20percent aq. H2SO4 / 2 h / Heating
3: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / dioxane / 2 h / Heating
4: 96.2 percent / H2 / PtO2 / ethanol; dioxane / 2 h / 760 Torr
5: 1.) 20percent aq. H2SO4, aq. NaNO2, 2.) H2O / 1.) 0-5 deg C, 15 min, 2.) reflux, 1 h
View Scheme
Acetic acid (4R,5bS,11aS)-4-acetoxy-4-ethyl-9-nitro-3,13-dioxo-3,4,5b,11a,12,13-hexahydro-1H,11H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-6-yl ester

Acetic acid (4R,5bS,11aS)-4-acetoxy-4-ethyl-9-nitro-3,13-dioxo-3,4,5b,11a,12,13-hexahydro-1H,11H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-6-yl ester

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

(S)-10-hydroxycamptothecin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 82.3 percent / 20percent aq. H2SO4 / 2 h / Heating
2: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / dioxane / 2 h / Heating
3: 96.2 percent / H2 / PtO2 / ethanol; dioxane / 2 h / 760 Torr
4: 1.) 20percent aq. H2SO4, aq. NaNO2, 2.) H2O / 1.) 0-5 deg C, 15 min, 2.) reflux, 1 h
View Scheme
(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
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

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

(S)-10-hydroxycamptothecin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 51 percent / Me6Sn2 / benzene / 5 h / 70 °C / Irradiation
2: 82 percent / aq. HBr / 72 h / 110 °C
View Scheme
(S)-10-hydroxycamptothecin
19685-09-7

(S)-10-hydroxycamptothecin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 45 percent / ICl / CCl4; CH2Cl2 / 48 h / Ambient temperature
2: 73 percent / Me3SiCl, NaI / acetonitrile; H2O / 5 h / 65 °C
3: 78 percent / NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide / 1.) 0 deg C, 10 min; r.t., 15 min, 2.) toluene, 70 deg C, 20 h
4: 51 percent / Me6Sn2 / benzene / 5 h / 70 °C / Irradiation
5: 82 percent / aq. HBr / 72 h / 110 °C
View Scheme
2-methoxy-6-(trimethylsilyl)pyridine
170453-55-1

2-methoxy-6-(trimethylsilyl)pyridine

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

(S)-10-hydroxycamptothecin

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: tBuLi
2: nBuLi, I2
3: 63 percent / Et3SiH / trifluoroacetic acid
4: 69 percent / K2CO3, Bu4NBr / Pd(OAc)2
5: 1.) OsO4, (DHQD)2-Pyr, 2.) I2, CaCO3
6: 47 percent / ICl
7: 72 percent / aq. HI
8: 88 percent / NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide
9: Me3SnSnMe3 / benzene / 70 °C / Irradiation
View Scheme
2-Methoxy-6-trimethylsilanyl-pyridine-3-carbaldehyde
453518-21-3

2-Methoxy-6-trimethylsilanyl-pyridine-3-carbaldehyde

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

(S)-10-hydroxycamptothecin

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: nBuLi, I2
2: 63 percent / Et3SiH / trifluoroacetic acid
3: 69 percent / K2CO3, Bu4NBr / Pd(OAc)2
4: 1.) OsO4, (DHQD)2-Pyr, 2.) I2, CaCO3
5: 47 percent / ICl
6: 72 percent / aq. HI
7: 88 percent / NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide
8: Me3SnSnMe3 / benzene / 70 °C / Irradiation
View Scheme
4-iodo-2-methoxy-6-trimethylsilanyl-3-pyridinecarboxaldehyde
174092-75-2

4-iodo-2-methoxy-6-trimethylsilanyl-3-pyridinecarboxaldehyde

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

(S)-10-hydroxycamptothecin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 63 percent / Et3SiH / trifluoroacetic acid
2: 69 percent / K2CO3, Bu4NBr / Pd(OAc)2
3: 1.) OsO4, (DHQD)2-Pyr, 2.) I2, CaCO3
4: 47 percent / ICl
5: 72 percent / aq. HI
6: 88 percent / NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide
7: Me3SnSnMe3 / benzene / 70 °C / Irradiation
View Scheme
3-[((E)-But-2-enyl)oxymethyl]-4-iodo-2-methoxy-6-trimethylsilanyl-pyridine

3-[((E)-But-2-enyl)oxymethyl]-4-iodo-2-methoxy-6-trimethylsilanyl-pyridine

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

(S)-10-hydroxycamptothecin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 69 percent / K2CO3, Bu4NBr / Pd(OAc)2
2: 1.) OsO4, (DHQD)2-Pyr, 2.) I2, CaCO3
3: 47 percent / ICl
4: 72 percent / aq. HI
5: 88 percent / NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide
6: Me3SnSnMe3 / benzene / 70 °C / Irradiation
View Scheme
(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
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

4-isocyanophenol
162471-15-0

4-isocyanophenol

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

(S)-10-hydroxycamptothecin

Conditions
ConditionsYield
With hexamethyldistannane In benzene at 70℃; Irradiation;
Camptothecin 1-oxide
86639-48-7

Camptothecin 1-oxide

acetic acid
64-19-7

acetic acid

A

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

(S)-10-hydroxycamptothecin

B

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

Conditions
ConditionsYield
With sulfuric acid In 1,4-dioxane for 0.5h; Irradiation;A 25%
B 30.5%
7-Methoxy-1,3-dihydro-pyrrolo[3,4-b]quinoline-2-carboxylic acid methyl ester
161681-89-6

7-Methoxy-1,3-dihydro-pyrrolo[3,4-b]quinoline-2-carboxylic acid methyl ester

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

(S)-10-hydroxycamptothecin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 30percent HBr/HOAc / 12 h / 20 °C
2: 89 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, 1-hydroxybenzotriazole (HOBT), Et3N / tetrahydrofuran
3: TFA / H2O; toluene
4: DDQ
5: diisobutylaluminum hydride (DIBAH) / CH2Cl2
6: 1.) NaBH4; 2.) aq. NaOH / 1.) MeOH
7: 72 percent / 48percent HBr
View Scheme
Multi-step reaction with 7 steps
1: 30percent HBr/HOAc / 12 h / 20 °C
2: 89 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, 1-hydroxybenzotriazole (HOBT), Et3N / tetrahydrofuran
3: TFA / H2O; toluene
4: DDQ
5: diisobutylaluminum hydride (DIBAH) / CH2Cl2
6: NaBH4 / methanol
7: 72 percent / 48percent HBr
View Scheme
2-(Methoxycarbonyl-prop-2-ynyl-amino)-N-(4-methoxy-phenyl)-acetimidic acid methyl ester

2-(Methoxycarbonyl-prop-2-ynyl-amino)-N-(4-methoxy-phenyl)-acetimidic acid methyl ester

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

(S)-10-hydroxycamptothecin

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: acetonitrile / 50 °C
2: 30percent HBr/HOAc / 12 h / 20 °C
3: 89 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, 1-hydroxybenzotriazole (HOBT), Et3N / tetrahydrofuran
4: TFA / H2O; toluene
5: DDQ
6: diisobutylaluminum hydride (DIBAH) / CH2Cl2
7: 1.) NaBH4; 2.) aq. NaOH / 1.) MeOH
8: 72 percent / 48percent HBr
View Scheme
Multi-step reaction with 8 steps
1: acetonitrile / 50 °C
2: 30percent HBr/HOAc / 12 h / 20 °C
3: 89 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, 1-hydroxybenzotriazole (HOBT), Et3N / tetrahydrofuran
4: TFA / H2O; toluene
5: DDQ
6: diisobutylaluminum hydride (DIBAH) / CH2Cl2
7: NaBH4 / methanol
8: 72 percent / 48percent HBr
View Scheme
2-[1-((2R,4S)-2-tert-Butyl-4-ethyl-5-oxo-[1,3]dioxolan-4-yl)-2,2-dimethoxy-ethyl]-malonic acid monomethyl ester

2-[1-((2R,4S)-2-tert-Butyl-4-ethyl-5-oxo-[1,3]dioxolan-4-yl)-2,2-dimethoxy-ethyl]-malonic acid monomethyl ester

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

(S)-10-hydroxycamptothecin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 89 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, 1-hydroxybenzotriazole (HOBT), Et3N / tetrahydrofuran
2: TFA / H2O; toluene
3: DDQ
4: diisobutylaluminum hydride (DIBAH) / CH2Cl2
5: 1.) NaBH4; 2.) aq. NaOH / 1.) MeOH
6: 72 percent / 48percent HBr
View Scheme
Multi-step reaction with 6 steps
1: 89 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, 1-hydroxybenzotriazole (HOBT), Et3N / tetrahydrofuran
2: TFA / H2O; toluene
3: DDQ
4: diisobutylaluminum hydride (DIBAH) / CH2Cl2
5: NaBH4 / methanol
6: 72 percent / 48percent HBr
View Scheme
7-Methoxy-2,3-dihydro-1H-pyrrolo[3,4-b]quinoline; hydrobromide

7-Methoxy-2,3-dihydro-1H-pyrrolo[3,4-b]quinoline; hydrobromide

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

(S)-10-hydroxycamptothecin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 89 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, 1-hydroxybenzotriazole (HOBT), Et3N / tetrahydrofuran
2: TFA / H2O; toluene
3: DDQ
4: diisobutylaluminum hydride (DIBAH) / CH2Cl2
5: 1.) NaBH4; 2.) aq. NaOH / 1.) MeOH
6: 72 percent / 48percent HBr
View Scheme
Multi-step reaction with 6 steps
1: 89 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, 1-hydroxybenzotriazole (HOBT), Et3N / tetrahydrofuran
2: TFA / H2O; toluene
3: DDQ
4: diisobutylaluminum hydride (DIBAH) / CH2Cl2
5: NaBH4 / methanol
6: 72 percent / 48percent HBr
View Scheme
(S)-10-hydroxycamptothecin
19685-09-7

(S)-10-hydroxycamptothecin

10-methoxycamptothecin
19685-10-0

10-methoxycamptothecin

Conditions
ConditionsYield
In 1,4-dioxane; methanol at 20℃; for 2h;100%
88%
In 1,4-dioxane; methanol; diethyl ether for 1h; Ambient temperature;87.5%
(S)-10-hydroxycamptothecin
19685-09-7

(S)-10-hydroxycamptothecin

4-piperidinopiperidine-1-carbonyl chloride
103816-19-9

4-piperidinopiperidine-1-carbonyl chloride

10-[4-(1-piperidino)-1-piperidino]carbonyloxycamptothecin
103816-16-6

10-[4-(1-piperidino)-1-piperidino]carbonyloxycamptothecin

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 4h;100%
(S)-10-hydroxycamptothecin
19685-09-7

(S)-10-hydroxycamptothecin

9-bromo-10-hydroxycamptothecin
1097323-11-9

9-bromo-10-hydroxycamptothecin

Conditions
ConditionsYield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 20℃; for 2h;98%
With N-Bromosuccinimide In N,N-dimethyl-formamide95%
N,N-phenylbistrifluoromethane-sulfonimide
37595-74-7

N,N-phenylbistrifluoromethane-sulfonimide

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

(S)-10-hydroxycamptothecin

10-hydroxy-(20S)-camptothecin trifluoromethanesulfonate
123949-09-7

10-hydroxy-(20S)-camptothecin trifluoromethanesulfonate

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 23 - 50℃; Inert atmosphere;97%
With triethylamine In N,N-dimethyl-formamide at 23 - 50℃;97%
With triethylamine In N,N-dimethyl-formamide at 20℃;96.7%
With triethylamine In N,N-dimethyl-formamide at 50℃; for 3h;
With triethylamine In N,N-dimethyl-formamide at 50℃;
(S)-10-hydroxycamptothecin
19685-09-7

(S)-10-hydroxycamptothecin

9-iodine-10-hydroxycamptothecin
1256544-04-3

9-iodine-10-hydroxycamptothecin

Conditions
ConditionsYield
With N-iodo-succinimide In N,N-dimethyl-formamide at 0 - 20℃; for 2h;97%
With N-iodo-succinimide In N,N-dimethyl-formamide at 0 - 20℃; for 2h;95%
1-chlorocarbonyl-4-piperidinopiperidine hydrochloride

1-chlorocarbonyl-4-piperidinopiperidine hydrochloride

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

(S)-10-hydroxycamptothecin

10-[4-(1-piperidino)-1-piperidino]carbonyloxycamptothecin hydrochloride

10-[4-(1-piperidino)-1-piperidino]carbonyloxycamptothecin hydrochloride

Conditions
ConditionsYield
With potassium carbonate; triethylamine In acetonitrile at 60℃; for 6h;97%
glutaric anhydride,
108-55-4

glutaric anhydride,

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

(S)-10-hydroxycamptothecin

C25H22N2O8

C25H22N2O8

Conditions
ConditionsYield
With pyridine at 25℃; for 72h;97%
(S)-10-hydroxycamptothecin
19685-09-7

(S)-10-hydroxycamptothecin

2-Methylpropionic anhydride
97-72-3

2-Methylpropionic anhydride

camptothecin 10,20-di-O-isobutyrate

camptothecin 10,20-di-O-isobutyrate

Conditions
ConditionsYield
sulfuric acid at 20 - 100℃; for 16h;96%
(S)-10-hydroxycamptothecin
19685-09-7

(S)-10-hydroxycamptothecin

10-hydroxy-mappicine ketone

10-hydroxy-mappicine ketone

Conditions
ConditionsYield
In various solvent(s) at 200℃; for 9h;95%
triethylsilyl chloride
994-30-9

triethylsilyl chloride

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

(S)-10-hydroxycamptothecin

20(S)-O-triethylsilylcampothecin
1004265-03-5

20(S)-O-triethylsilylcampothecin

Conditions
ConditionsYield
Stage #1: (S)-10-hydroxycamptothecin With 1H-imidazole In N,N-dimethyl-formamide for 0.166667h; Inert atmosphere;
Stage #2: triethylsilyl chloride With dmap In N,N-dimethyl-formamide
94%
Stage #1: (S)-10-hydroxycamptothecin With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: triethylsilyl chloride With dmap In N,N-dimethyl-formamide at 20℃; for 60h; Inert atmosphere;
94%
With 1H-imidazole; dmap In N,N-dimethyl-formamide for 24.1667h;94%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

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

(S)-10-hydroxycamptothecin

10-tert-butoxycarbonyloxycamptothecin
362496-88-6

10-tert-butoxycarbonyloxycamptothecin

Conditions
ConditionsYield
With pyridine In N,N-dimethyl-formamide at 20℃;94%
With pyridine In N,N-dimethyl-formamide at 20℃;
With pyridine In N,N-dimethyl-formamide at 20℃;2.1 g
With pyridine In dichloromethane
In pyridine; N,N-dimethyl-formamide at 20℃; Inert atmosphere;
glutaric anhydride,
108-55-4

glutaric anhydride,

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

(S)-10-hydroxycamptothecin

C25H22N2O8
1353778-70-7

C25H22N2O8

Conditions
ConditionsYield
With pyridine at 20℃; for 48h;94%
With pyridine at 20℃;59.22%
(S)-10-hydroxycamptothecin
19685-09-7

(S)-10-hydroxycamptothecin

4-Nitrophenyl chloroformate
7693-46-1

4-Nitrophenyl chloroformate

4-nitrophenyl camptothecin-10-yl carbonate
656233-42-0

4-nitrophenyl camptothecin-10-yl carbonate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; for 1h; Schlenk technique;93%
With triethylamine In tetrahydrofuran at 0 - 20℃; for 1h;93%
With triethylamine at 20℃; for 1h;91%
(S)-10-hydroxycamptothecin
19685-09-7

(S)-10-hydroxycamptothecin

C39H50N4O12
945867-58-3

C39H50N4O12

Conditions
ConditionsYield
With triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2h;92%
(S)-10-hydroxycamptothecin
19685-09-7

(S)-10-hydroxycamptothecin

Cyclohexanecarboxylic acid

Cyclohexanecarboxylic acid

(S)-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 cyclohexanecarboxylate

(S)-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 cyclohexanecarboxylate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;92%
(S)-10-hydroxycamptothecin
19685-09-7

(S)-10-hydroxycamptothecin

Topotecan hydrochloride
119413-54-6, 123949-07-5

Topotecan hydrochloride

Conditions
ConditionsYield
In propan-1-ol; dichloromethane91%
formaldehyd
50-00-0

formaldehyd

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

(S)-10-hydroxycamptothecin

(S)-1-Pyrrolidin-2-yl-methanol

(S)-1-Pyrrolidin-2-yl-methanol

10-hydroxyl-9-L-prolinol (+)methylcamptothecin
1439356-77-0

10-hydroxyl-9-L-prolinol (+)methylcamptothecin

Conditions
ConditionsYield
In acetic acid at 40 - 90℃; Mannich Aminomethylation;90.2%
methanol
67-56-1

methanol

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

(S)-10-hydroxycamptothecin

7-hydroxymethyl-10-hydroxycamptothecin
86639-61-4

7-hydroxymethyl-10-hydroxycamptothecin

Conditions
ConditionsYield
With sulfuric acid; dihydrogen peroxide; iron(II) sulfate at 20℃; for 96h; hydroxymethylation;90%
2-(hydroxymethyl)-1H-isoindole-1,3(2H)-dione
118-29-6

2-(hydroxymethyl)-1H-isoindole-1,3(2H)-dione

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

(S)-10-hydroxycamptothecin

C29H21N3O7
1352172-54-3

C29H21N3O7

Conditions
ConditionsYield
With sulfuric acid at 0 - 20℃; for 12h;90%
N-hydroxymethyl-3,4,5,6-tetrahydrophthalimide
4887-42-7

N-hydroxymethyl-3,4,5,6-tetrahydrophthalimide

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

(S)-10-hydroxycamptothecin

C29H25N3O7
1352172-55-4

C29H25N3O7

Conditions
ConditionsYield
With sulfuric acid at 0 - 20℃; for 12h;90%
(S)-10-hydroxycamptothecin
19685-09-7

(S)-10-hydroxycamptothecin

prenyl bromide
870-63-3

prenyl bromide

(S)-4-ethyl-4-hydroxy-9-((3-methylbut-2-en-1-yl)oxy)-1,12-dihydro-14H-pyrano[3’,4’:6,7]indolizino[1,2-b]quinoline-3,14(4H)-dione

(S)-4-ethyl-4-hydroxy-9-((3-methylbut-2-en-1-yl)oxy)-1,12-dihydro-14H-pyrano[3’,4’:6,7]indolizino[1,2-b]quinoline-3,14(4H)-dione

Conditions
ConditionsYield
With potassium carbonate In acetone for 3h; Reflux;90%
(S)-10-hydroxycamptothecin
19685-09-7

(S)-10-hydroxycamptothecin

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

carbonic acid 4-ethoxycarbonyloxy-4-ethyl-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-9-yl ester ethyl ester

carbonic acid 4-ethoxycarbonyloxy-4-ethyl-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-9-yl ester ethyl ester

Conditions
ConditionsYield
With pyridine In 1,2-dichloro-ethane89.2%
(S)-10-hydroxycamptothecin
19685-09-7

(S)-10-hydroxycamptothecin

poly(ethylene glycol)-O-glycolic acid ether

poly(ethylene glycol)-O-glycolic acid ether

10-camptothecin-[poly(ethylene glycol)-O-glycolic acid ether] ester, Mw=40000

10-camptothecin-[poly(ethylene glycol)-O-glycolic acid ether] ester, Mw=40000

Conditions
ConditionsYield
With pyridine; O-phenyl phosphorodichloridate In chloroform at 20℃; for 18h;89%
C21H38N2O8
945867-57-2

C21H38N2O8

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

(S)-10-hydroxycamptothecin

C41H54N4O13
945867-59-4

C41H54N4O13

Conditions
ConditionsYield
With triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2h;89%
butanoic acid anhydride
106-31-0

butanoic acid anhydride

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

(S)-10-hydroxycamptothecin

camptothecin 10,20-di-O-butyrate

camptothecin 10,20-di-O-butyrate

Conditions
ConditionsYield
sulfuric acid at 20 - 100℃;89%
1,3,6,9,12-pentaoxa-2-thiacyclotetradecane 2,2-dioxide

1,3,6,9,12-pentaoxa-2-thiacyclotetradecane 2,2-dioxide

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

(S)-10-hydroxycamptothecin

C28H32N2O9

C28H32N2O9

Conditions
ConditionsYield
Stage #1: 1,3,6,9,12-pentaoxa-2-thiacyclotetradecane 2,2-dioxide; (S)-10-hydroxycamptothecin With potassium carbonate In N,N-dimethyl-formamide at 40℃;
Stage #2: With sulfuric acid In tetrahydrofuran; water for 3h; Reflux;
89%
(S)-10-hydroxycamptothecin
19685-09-7

(S)-10-hydroxycamptothecin

allyl bromide
106-95-6

allyl bromide

10-allyloxycamptothecin
185425-24-5

10-allyloxycamptothecin

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;88.2%
With potassium carbonate In N,N-dimethyl-formamide
C10H20O8S

C10H20O8S

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

(S)-10-hydroxycamptothecin

C30H36N2O10

C30H36N2O10

Conditions
ConditionsYield
Stage #1: C10H20O8S; (S)-10-hydroxycamptothecin With potassium carbonate In N,N-dimethyl-formamide at 40℃;
Stage #2: With sulfuric acid In tetrahydrofuran; water for 3h; Reflux;
88%
C18H36O12S

C18H36O12S

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

(S)-10-hydroxycamptothecin

C38H52N2O14

C38H52N2O14

Conditions
ConditionsYield
Stage #1: C18H36O12S; (S)-10-hydroxycamptothecin With potassium carbonate In N,N-dimethyl-formamide at 40℃;
Stage #2: With sulfuric acid In tetrahydrofuran; water for 3h; Reflux;
88%

19685-09-7Related news

Original articleStudy the voltammetric behavior of 10-Hydroxycamptothecin (cas 19685-09-7) and its sensitive determination at electrochemically reduced graphene oxide modified glassy carbon electrode09/08/2019

The electrochemical properties of 10-Hydroxycamptothecin were investigated systematically at a reduced graphene oxide modified glassy carbon electrode. A new pair of redox peaks of 10-Hydroxycamptothecin was reported for the first time with quasi-reversible process driven by adsorption. The dyna...detailed

An efficient approach for the enzyme-enhanced extraction of camptothecin and 10-Hydroxycamptothecin (cas 19685-09-7) from the samara of Camptotheca acuminata using an ionic liquid solution09/06/2019

An efficient approach for enzyme-enhanced extraction using an ionic liquid solution (ILEEE) of the major alkaloidal components camptothecin (CPT) and 10-hydroxycamptothecin (HCPT) from the samara of Camptotheca acuminata is presented. The enzyme pretreatment in an aqueous ionic liquid (IL) media...detailed

Incorporation of 10-Hydroxycamptothecin (cas 19685-09-7) nanocrystals into zein microspheres09/04/2019

Incorporation of drug nanocrystal (DNC) into a particulate carrier to form the DNC delivery system was conducted in this study, where 10-hydroxycamptothecin (HCPT) was selected as the model drug and zein was the carrier. The supercritical anti-solvent (SAS) process or the built-in ultrasonic dia...detailed

Monodisperse oligoethylene glycols modified Camptothecin, 10-Hydroxycamptothecin (cas 19685-09-7) and SN38 prodrugs09/03/2019

Camptothecin, which represents a class of natural products with high anticancer activity, suffers low water solubility which hampers its clinic application. To address this issue, monodisperse polyethylene glycols were employed to modify this class of natural products, including Camptothecin, 10...detailed

ORIGINAL ARTICLEMenthol-modified casein nanoparticles loading 10-Hydroxycamptothecin (cas 19685-09-7) for glioma targeting therapy09/02/2019

Chemotherapy outcomes for the treatment of glioma remains unsatisfactory due to the inefficient drug transport across the bloodbrain barrier (BBB) and insufficient drug accumulation in the tumor region. Although many approaches, including various nanosystems, have been developed to promote the d...detailed

Full Length ArticleSelf-assembly behavior of amphiphilic poly(ethylene glycol)-conjugated 10-Hydroxycamptothecin (cas 19685-09-7) in water and its cytotoxicity assay09/01/2019

A PEGylated 10-hydroxycamptothecin (HCPT) conjugate, an amphiphilic prodrug, in which two hydrophobic HCPT molecules were conjugated to the two ends of a hydrophilic poly(ethylene glycol) bis(carboxymethyl) ether (PEG-biCOOH) molecule, was synthesized by esterification of the terminal carboxylic...detailed

19685-09-7Relevant articles and documents

Short protecting group-free syntheses of camptothecin and 10-hydroxycamptothecin using cascade methodologies

Xu, Peng,Chen, Dong-Sheng,Xi, Jie,Yao, Zhu-Jun

, p. 976 - 981 (2015)

A convergent protecting group-free total synthesis route of camptothecin and 10-hydroxycamptothecin has been developed in this work. Cascade oxidation of 3-(hydroxymethyl)furan-2(5 H)-one and in situ intermolecular oxa Diels-Alder reaction with vinyl ether was developed and applied to construct the E-ring, and TMSCl-promoted cascade closure of the D-ring delivered the whole skeleton of the alkaloids in the total synthesis. The new short syntheses were advantageous with regard to step economy, low cost, easily available starting materials and reagents, and convenient operations.

An efficient conversion of camptothecin to 10-hydroxycamptothecin

Wood,Fortunak,Mastrocola,Mellinger,Burk

, p. 5739 - 5740 (1995)

-

Multi-gram scale synthesis of a bleomycin (BLM) carbohydrate moiety: exploring the antitumor beneficial effect of BLM disaccharide attached to 10-hydroxycamptothecine (10-HCPT)

Li, MaoLin,Huang, Weiping,Jiang, Zhilin,Shi, Yonghui,Yuan, Sisi,Fu, Kaishuo,Chen, YongJun,Zhou, Li,Zhou, Wen

, p. 6010 - 6020 (2019/04/17)

The “tumor-seeking” role of bleomycin (BLM) disaccharide has been demonstrated to serve as a promising tool for cancer diagnosis and a potential ligand for targeted therapy. However, these practical applications are often hampered by the lack of BLM disaccharide. Herein, an efficient multi-gram synthesis of peracetylated BLM disaccharide 20 is achieved by a TMSOTF-mediated glycosidation coupling manner in 43.6% overall yield in terms of benzyl galactoside. The critical innovation of the synthetic strategy is that inexpensive benzyl galactoside was first adopted to prepare an l-gulose subunit 3 as a glycosyl acceptor, with a much shorter route in 73.0% yield, and a 3-O-carbamoyl-mannose donor 4 was achieved in 47.2% yield by lowering the amount of dibutyltin oxide, and merging aminolysis and selective deacetylation into a one-pot reaction. Next, the incorporation of BLM disaccharide into 10-hydroxycamptothecin (10-HCPT), a non-specific model compound, to form conjugate 1 could significantly improve the antitumor activity and display obvious selectivity toward cancerous and normal cells in comparison with 10-HCPT. Moreover, BLM disaccharide itself was non-cytotoxic, clearly indicating the importance and potential of BLM disaccharide in solving the targeted antitumor therapy of cytotoxic drugs.

Total synthesis of camptothecin and SN-38

Yu, Shanbao,Huang, Qing-Qing,Luo, Yu,Lu, Wei

experimental part, p. 713 - 717 (2012/03/11)

A new practical and concise total synthesis of enantiopure camptothecin and SN-38 (14% overall yield, 99.9% ee and 99.9% purity) was described, starting from inexpensive and readily available materials. The development of column chromatography-free purification was achieved in all steps, which offers an economic industrial process to the camptothecin-family alkaloids.

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 19685-09-7