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  • 78287-27-1 Structure
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    1. Product Name: 7-Ethylcamptothecin
    2. Synonyms: Irinotecan USP RC E;7-ETHYL-CAMPTOTHECIN,HPLC 99%;(S)-4,11-Diethyl-4-hydroxy-1H-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione;(4S)-4,11-Diethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione;SN 22;7-Etyl-camptothecin;(4S)-4,11-Diethyl-4-hydroxy-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione;7-Ethylcamptothecin
    3. CAS NO:78287-27-1
    4. Molecular Formula: C22H20N2O4
    5. Molecular Weight: 376.4
    6. EINECS: N/A
    7. Product Categories: Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
    8. Mol File: 78287-27-1.mol
    9. Article Data: 12
  • Chemical Properties

    1. Melting Point: 236-241°C
    2. Boiling Point: 752.867 °C at 760 mmHg
    3. Flash Point: 409.119 °C
    4. Appearance: light pink solid
    5. Density: 1.43
    6. Vapor Pressure: 8.15E-24mmHg at 25°C
    7. Refractive Index: 1.712
    8. Storage Temp.: -20°C Freezer
    9. Solubility: Chloroform and Methanol Mixture (Slightly, Heated, Sonicated), DMSO (Slightly, H
    10. PKA: 11.24±0.20(Predicted)
    11. CAS DataBase Reference: 7-Ethylcamptothecin(CAS DataBase Reference)
    12. NIST Chemistry Reference: 7-Ethylcamptothecin(78287-27-1)
    13. EPA Substance Registry System: 7-Ethylcamptothecin(78287-27-1)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: 23/34/35
    3. Safety Statements: 3/14-6-36/37/39
    4. RIDADR: 1544
    5. WGK Germany:
    6. RTECS:
    7. HazardClass: 6.1
    8. PackingGroup: III
    9. Hazardous Substances Data: 78287-27-1(Hazardous Substances Data)

78287-27-1 Usage

Description

7-Ethylcamptothecin is a synthetic Camptothecin (CPT) derivative, characterized as a light pink solid. It is an antineoplastic agent that exhibits strong activity against various murine tumors and is particularly effective against drug-resistant tumors.

Uses

Used in Pharmaceutical Industry:
7-Ethylcamptothecin is used as an anticancer drug for its potent activity against a range of murine tumors. It is valued for its ability to combat drug-resistant tumors, making it a promising candidate in the development of novel cancer therapies.
Used in Cancer Research:
As a CPT derivative, 7-Ethylcamptothecin is utilized in cancer research to study the mechanisms of action and resistance patterns in various types of cancer. This helps in the advancement of targeted therapies and the understanding of tumor biology.
Used in Drug Development:
7-Ethylcamptothecin serves as a key component in the development of new antineoplastic drugs. Its properties are harnessed to create innovative formulations and drug delivery systems aimed at improving the efficacy and safety of cancer treatments.
Used in Quality Control:
As Irinotecan USP Related Compound E, 7-Ethylcamptothecin is used in the quality control processes of pharmaceutical manufacturing. It ensures the consistency, purity, and potency of the final drug product, maintaining high standards in the pharmaceutical industry.

Biological Activity

7-Ethylcamptothecin is one of the camptothecin analogs. Camptothecin (CPT), a cytotoxic alkaloid isolated from camptothecin analogues, has strong antitumor activity against L1210 leukemia and Walker 256 carcinosarcoma models.

Check Digit Verification of cas no

The CAS Registry Mumber 78287-27-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,8,2,8 and 7 respectively; the second part has 2 digits, 2 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 78287-27:
(7*7)+(6*8)+(5*2)+(4*8)+(3*7)+(2*2)+(1*7)=171
171 % 10 = 1
So 78287-27-1 is a valid CAS Registry Number.
InChI:InChI=1/C22H20N2O4/c1-3-12-13-7-5-6-8-17(13)23-19-14(12)10-24-18(19)9-16-15(20(24)25)11-28-21(26)22(16,27)4-2/h5-9,27H,3-4,10-11H2,1-2H3/t22-/m0/s1

78287-27-1 Well-known Company Product Price

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  • (Code)Product description
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  • TCI America

  • (E0781)  7-Ethylcamptothecin  >96.0%(HPLC)

  • 78287-27-1

  • 100mg

  • 680.00CNY

  • Detail
  • TCI America

  • (E0781)  7-Ethylcamptothecin  >96.0%(HPLC)

  • 78287-27-1

  • 1g

  • 3,890.00CNY

  • Detail

78287-27-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 7-Ethylcamptothecin

1.2 Other means of identification

Product number -
Other names (S)-4,11-Diethyl-4-hydroxy-1H-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione

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:78287-27-1 SDS

78287-27-1Synthetic route

propionaldehyde
123-38-6

propionaldehyde

camptothecin
7689-03-4

camptothecin

7-ethylcamptothecin
78287-27-1

7-ethylcamptothecin

Conditions
ConditionsYield
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%
tert-amyl hydroperoxide
3425-61-4

tert-amyl hydroperoxide

camptothecin
7689-03-4

camptothecin

7-ethylcamptothecin
78287-27-1

7-ethylcamptothecin

Conditions
ConditionsYield
With sulfuric acid; iron(II) sulfate; acetic acid In water at 0℃; for 0.5h;83.3%
Acetic acid 7-[(S)-1-(2-dimethylamino-ethylcarbamoyl)-1-hydroxy-propyl]-12-ethyl-9-oxo-9,11-dihydro-indolizino[1,2-b]quinolin-8-ylmethyl ester
148550-34-9

Acetic acid 7-[(S)-1-(2-dimethylamino-ethylcarbamoyl)-1-hydroxy-propyl]-12-ethyl-9-oxo-9,11-dihydro-indolizino[1,2-b]quinolin-8-ylmethyl ester

A

7-ethylcamptothecin
78287-27-1

7-ethylcamptothecin

B

(S)-2-Amino-4,11-diethyl-4-hydroxy-1,12-dihydro-2H,4H-2,6,12a-triaza-dibenzo[b,h]fluorene-3,13-dione
152266-85-8

(S)-2-Amino-4,11-diethyl-4-hydroxy-1,12-dihydro-2H,4H-2,6,12a-triaza-dibenzo[b,h]fluorene-3,13-dione

Conditions
ConditionsYield
With hydrazine hydrate In methanol for 2.5h; Heating;A 74%
B 11%
Ethyl boronic acid
4433-63-0

Ethyl boronic acid

camptothecin
7689-03-4

camptothecin

7-ethylcamptothecin
78287-27-1

7-ethylcamptothecin

Conditions
ConditionsYield
With tris(2,2'-bipyridyl)ruthenium dichloride; 1-acetoxy-1,2-benziodoxol-3-one at 30℃; for 48h; Minisci Aromatic Substitution; Inert atmosphere; Irradiation;60%
propan-1-ol
71-23-8

propan-1-ol

camptothecin
7689-03-4

camptothecin

A

7-ethylcamptothecin
78287-27-1

7-ethylcamptothecin

B

7(3-Hydroxy-1-propyl)camptothecin
139080-89-0

7(3-Hydroxy-1-propyl)camptothecin

C

7-(1-Hydroxy-2-propyl)camptothecin
96962-27-5

7-(1-Hydroxy-2-propyl)camptothecin

Conditions
ConditionsYield
With sulfuric acid; dihydrogen peroxide; iron(II) sulfate In water for 3h; Ambient temperature;A 40%
B 12%
C 22%
camptothecin
7689-03-4

camptothecin

pentan-3-one
96-22-0

pentan-3-one

7-ethylcamptothecin
78287-27-1

7-ethylcamptothecin

Conditions
ConditionsYield
With sulfuric acid; dihydrogen peroxide; iron(II) sulfate In water; acetic acid for 48h; Ambient temperature;22%
propionic acid
802294-64-0

propionic acid

camptothecin
7689-03-4

camptothecin

7-ethylcamptothecin
78287-27-1

7-ethylcamptothecin

Conditions
ConditionsYield
With sulfuric acid; dihydrogen peroxide; iron(II) sulfate In water for 48h; Ambient temperature;13%
Isobutyric acid 7-[(S)-1-(2-dimethylamino-ethylcarbamoyl)-1-hydroxy-propyl]-12-ethyl-9-oxo-9,11-dihydro-indolizino[1,2-b]quinolin-8-ylmethyl ester
148550-35-0

Isobutyric acid 7-[(S)-1-(2-dimethylamino-ethylcarbamoyl)-1-hydroxy-propyl]-12-ethyl-9-oxo-9,11-dihydro-indolizino[1,2-b]quinolin-8-ylmethyl ester

A

7-ethylcamptothecin
78287-27-1

7-ethylcamptothecin

B

(S)-2-Amino-4,11-diethyl-4-hydroxy-1,12-dihydro-2H,4H-2,6,12a-triaza-dibenzo[b,h]fluorene-3,13-dione
152266-85-8

(S)-2-Amino-4,11-diethyl-4-hydroxy-1,12-dihydro-2H,4H-2,6,12a-triaza-dibenzo[b,h]fluorene-3,13-dione

Conditions
ConditionsYield
With hydrazine hydrate In methanol for 2.5h; Heating;A 10 % Chromat.
B 16 % Chromat.
Benzoic acid 7-[(S)-1-(2-dimethylamino-ethylcarbamoyl)-1-hydroxy-propyl]-12-ethyl-9-oxo-9,11-dihydro-indolizino[1,2-b]quinolin-8-ylmethyl ester
120730-50-9

Benzoic acid 7-[(S)-1-(2-dimethylamino-ethylcarbamoyl)-1-hydroxy-propyl]-12-ethyl-9-oxo-9,11-dihydro-indolizino[1,2-b]quinolin-8-ylmethyl ester

A

7-ethylcamptothecin
78287-27-1

7-ethylcamptothecin

B

(S)-2-Amino-4,11-diethyl-4-hydroxy-1,12-dihydro-2H,4H-2,6,12a-triaza-dibenzo[b,h]fluorene-3,13-dione
152266-85-8

(S)-2-Amino-4,11-diethyl-4-hydroxy-1,12-dihydro-2H,4H-2,6,12a-triaza-dibenzo[b,h]fluorene-3,13-dione

Conditions
ConditionsYield
With hydrazine hydrate In methanol for 2.5h; Heating;A 38 % Chromat.
B 36 % Chromat.
4-Methoxy-benzoic acid 7-[(S)-1-(2-dimethylamino-ethylcarbamoyl)-1-hydroxy-propyl]-12-ethyl-9-oxo-9,11-dihydro-indolizino[1,2-b]quinolin-8-ylmethyl ester
120730-51-0

4-Methoxy-benzoic acid 7-[(S)-1-(2-dimethylamino-ethylcarbamoyl)-1-hydroxy-propyl]-12-ethyl-9-oxo-9,11-dihydro-indolizino[1,2-b]quinolin-8-ylmethyl ester

A

7-ethylcamptothecin
78287-27-1

7-ethylcamptothecin

B

(S)-2-Amino-4,11-diethyl-4-hydroxy-1,12-dihydro-2H,4H-2,6,12a-triaza-dibenzo[b,h]fluorene-3,13-dione
152266-85-8

(S)-2-Amino-4,11-diethyl-4-hydroxy-1,12-dihydro-2H,4H-2,6,12a-triaza-dibenzo[b,h]fluorene-3,13-dione

Conditions
ConditionsYield
With hydrazine hydrate In methanol for 2.5h; Heating;A 20 % Chromat.
B 46 % Chromat.
4-Cyano-benzoic acid 7-[(S)-1-(2-dimethylamino-ethylcarbamoyl)-1-hydroxy-propyl]-12-ethyl-9-oxo-9,11-dihydro-indolizino[1,2-b]quinolin-8-ylmethyl ester

4-Cyano-benzoic acid 7-[(S)-1-(2-dimethylamino-ethylcarbamoyl)-1-hydroxy-propyl]-12-ethyl-9-oxo-9,11-dihydro-indolizino[1,2-b]quinolin-8-ylmethyl ester

A

7-ethylcamptothecin
78287-27-1

7-ethylcamptothecin

B

(S)-2-Amino-4,11-diethyl-4-hydroxy-1,12-dihydro-2H,4H-2,6,12a-triaza-dibenzo[b,h]fluorene-3,13-dione
152266-85-8

(S)-2-Amino-4,11-diethyl-4-hydroxy-1,12-dihydro-2H,4H-2,6,12a-triaza-dibenzo[b,h]fluorene-3,13-dione

Conditions
ConditionsYield
With hydrazine hydrate In methanol for 2.5h; Heating;A 42 % Chromat.
B 46 % Chromat.
ferrous(II) sulfate heptahydrate

ferrous(II) sulfate heptahydrate

propionaldehyde
123-38-6

propionaldehyde

camptothecin
7689-03-4

camptothecin

7-ethylcamptothecin
78287-27-1

7-ethylcamptothecin

Conditions
ConditionsYield
With sulfuric acid; dihydrogen peroxide; acetic acid In water
ferrous(II) sulfate heptahydrate

ferrous(II) sulfate heptahydrate

camptothecin
7689-03-4

camptothecin

7-ethylcamptothecin
78287-27-1

7-ethylcamptothecin

Conditions
ConditionsYield
With sulfuric acid; dihydrogen peroxide; propionic acid In water
propan-1-ol
71-23-8

propan-1-ol

ferrous(II) sulfate heptahydrate

ferrous(II) sulfate heptahydrate

camptothecin
7689-03-4

camptothecin

7-ethylcamptothecin
78287-27-1

7-ethylcamptothecin

Conditions
ConditionsYield
With sulfuric acid; dihydrogen peroxide In water
ferrous(II) sulfate heptahydrate

ferrous(II) sulfate heptahydrate

camptothecin
7689-03-4

camptothecin

pentan-3-one
96-22-0

pentan-3-one

7-ethylcamptothecin
78287-27-1

7-ethylcamptothecin

Conditions
ConditionsYield
With sulfuric acid; dihydrogen peroxide; acetic acid In water
7-ethyl-18,19-dehydrocamptothecin
955939-02-3

7-ethyl-18,19-dehydrocamptothecin

7-ethylcamptothecin
78287-27-1

7-ethylcamptothecin

Conditions
ConditionsYield
With hydrogen; palladium 10% on activated carbon In 1,4-dioxane; ethanol at 20℃; for 1 - 7h;
acetaldehyde
75-07-0

acetaldehyde

camptothecin
7689-03-4

camptothecin

7-ethylcamptothecin
78287-27-1

7-ethylcamptothecin

Conditions
ConditionsYield
With ferrous(II) sulfate heptahydrate; sulfuric acid; dihydrogen peroxide In water at 0℃; for 8h;
7-ethylcamptothecin
78287-27-1

7-ethylcamptothecin

7-ethyl-1,2,6,7-tetrahydro-20-(S)-camptothecin
797762-11-9

7-ethyl-1,2,6,7-tetrahydro-20-(S)-camptothecin

Conditions
ConditionsYield
With hydrogen; N113 In acetic acid at 110℃; under 15001.5 Torr; for 6h; Autoclave;96%
With hydrogen; dimethyl sulfoxide; platinum on carbon In acetic acid at 25 - 65℃; under 3750.38 Torr; for 43.5h;
t-Boc-L-valine
13734-41-3

t-Boc-L-valine

7-ethylcamptothecin
78287-27-1

7-ethylcamptothecin

C32H37N3O7

C32H37N3O7

Conditions
ConditionsYield
With dmap In dichloromethane at 20℃; for 20h;92%
7-ethylcamptothecin
78287-27-1

7-ethylcamptothecin

5-fluorouracil-1-acetic acid
56059-30-4

5-fluorouracil-1-acetic acid

C28H23FN4O7

C28H23FN4O7

Conditions
ConditionsYield
Stage #1: 5-fluorouracil-1-acetic acid With pyridine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 0℃;
Stage #2: 7-ethylcamptothecin at 0 - 20℃; Inert atmosphere;
88%
uracilacetic acid
4113-97-7

uracilacetic acid

7-ethylcamptothecin
78287-27-1

7-ethylcamptothecin

C28H24N4O7

C28H24N4O7

Conditions
ConditionsYield
Stage #1: uracilacetic acid With pyridine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 0℃;
Stage #2: 7-ethylcamptothecin at 0 - 20℃; Inert atmosphere;
86.6%
7-ethylcamptothecin
78287-27-1

7-ethylcamptothecin

2-(5-iodo-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetic acid
57846-83-0

2-(5-iodo-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetic acid

C28H23IN4O7

C28H23IN4O7

Conditions
ConditionsYield
Stage #1: 2-(5-iodo-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetic acid With pyridine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 0℃;
Stage #2: 7-ethylcamptothecin at 0 - 20℃; Inert atmosphere;
86.6%
7-ethylcamptothecin
78287-27-1

7-ethylcamptothecin

isopropylamine
75-31-0

isopropylamine

(S)-2-(12-Ethyl-8-hydroxymethyl-9-oxo-9,11-dihydro-indolizino[1,2-b]quinolin-7-yl)-2-hydroxy-N-isopropyl-butyramide

(S)-2-(12-Ethyl-8-hydroxymethyl-9-oxo-9,11-dihydro-indolizino[1,2-b]quinolin-7-yl)-2-hydroxy-N-isopropyl-butyramide

Conditions
ConditionsYield
for 1.5h; Heating;86%
1-carboxymethyl-5-chlorouracil
95209-81-7

1-carboxymethyl-5-chlorouracil

7-ethylcamptothecin
78287-27-1

7-ethylcamptothecin

C28H23ClN4O7

C28H23ClN4O7

Conditions
ConditionsYield
Stage #1: 1-carboxymethyl-5-chlorouracil With pyridine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 0℃;
Stage #2: 7-ethylcamptothecin at 0 - 20℃; Inert atmosphere;
84%
p-nitrobenzotrifluoride
402-54-0

p-nitrobenzotrifluoride

7-ethylcamptothecin
78287-27-1

7-ethylcamptothecin

7-ethylcamptothecin-20(S)-O-p-triflouoromethylbenzoate

7-ethylcamptothecin-20(S)-O-p-triflouoromethylbenzoate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 2 - 20℃; for 2.25h;82%
7-ethylcamptothecin
78287-27-1

7-ethylcamptothecin

7-ethyl-10-hydroxycamptothecin
86639-52-3, 110714-48-2, 130144-34-2

7-ethyl-10-hydroxycamptothecin

Conditions
ConditionsYield
With dihydrogen peroxide; acetic anhydride; acetic acid at 50℃;80.3%
Multi-step reaction with 2 steps
1: 77.7 percent / 30percent aq. H2O2, acetic acid / 3.5 h / 70 - 80 °C
2: 49.1 percent / 1 N aq. H2SO4 / dioxane / 0.5 h / Irradiation
View Scheme
Multi-step reaction with 2 steps
1: 78 percent / 30percent H2O2 / acetic acid / 3.5 h / 70 - 80 °C
2: 49 percent / 1 N H2SO4 / dioxane / 0.5 h / Irradiation
View Scheme
Stage #1: 7-ethylcamptothecin With hydrogen; acetic acid; platinum(IV) oxide In dimethyl sulfoxide at 50 - 60℃; under 3102.97 Torr; for 10h;
Stage #2: With [bis(acetoxy)iodo]benzene In water at 20℃; for 3h;
Multi-step reaction with 2 steps
1: acetic acid; dihydrogen peroxide / 8 h / 80 °C
2: sulfuric acid; water / 1,4-dioxane; acetonitrile / Inert atmosphere; Irradiation
View Scheme
(5-bromouracil)acetic acid
31385-63-4

(5-bromouracil)acetic acid

7-ethylcamptothecin
78287-27-1

7-ethylcamptothecin

C28H23BrN4O7

C28H23BrN4O7

Conditions
ConditionsYield
Stage #1: (5-bromouracil)acetic acid With pyridine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 0℃;
Stage #2: 7-ethylcamptothecin at 0 - 20℃; Inert atmosphere;
80%
7-ethylcamptothecin
78287-27-1

7-ethylcamptothecin

7-Ethylcamptothecin 1-Oxide
86639-51-2

7-Ethylcamptothecin 1-Oxide

Conditions
ConditionsYield
With dihydrogen peroxide In acetic acid at 70 - 80℃; for 3.5h;78%
With dihydrogen peroxide; acetic acid at 70 - 80℃; for 3.5h;77.7%
With dihydrogen peroxide; acetic acid at 80℃; for 8h;72%
7-ethylcamptothecin
78287-27-1

7-ethylcamptothecin

3-nitrobenzoic acid
121-92-6

3-nitrobenzoic acid

7-ethylcamptothecin-20(S)-O-m-nitrobenzoate

7-ethylcamptothecin-20(S)-O-m-nitrobenzoate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 2 - 20℃; for 2.25h;77.1%
7-ethylcamptothecin
78287-27-1

7-ethylcamptothecin

N,N-dimethylethylenediamine
108-00-9

N,N-dimethylethylenediamine

(S)-N-(2-Dimethylamino-ethyl)-2-(12-ethyl-8-hydroxymethyl-9-oxo-9,11-dihydro-indolizino[1,2-b]quinolin-7-yl)-2-hydroxy-butyramide
120730-44-1

(S)-N-(2-Dimethylamino-ethyl)-2-(12-ethyl-8-hydroxymethyl-9-oxo-9,11-dihydro-indolizino[1,2-b]quinolin-7-yl)-2-hydroxy-butyramide

Conditions
ConditionsYield
at 50℃; for 1.5h;71%
7-ethylcamptothecin
78287-27-1

7-ethylcamptothecin

propargyl bromide
106-96-7

propargyl bromide

2-propyn-1-yl-7-ethylcamptothecin

2-propyn-1-yl-7-ethylcamptothecin

Conditions
ConditionsYield
Stage #1: 7-ethylcamptothecin With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; Inert atmosphere;
Stage #2: propargyl bromide In N,N-dimethyl-formamide Inert atmosphere; Reflux;
70%
7-ethylcamptothecin
78287-27-1

7-ethylcamptothecin

2-Amino-4,11-diethyl-2H,12H-2,6,12a-triaza-dibenzo[b,h]fluorene-3,13-dione

2-Amino-4,11-diethyl-2H,12H-2,6,12a-triaza-dibenzo[b,h]fluorene-3,13-dione

Conditions
ConditionsYield
With hydrazine hydrate for 2h; Heating;64%
7-ethylcamptothecin
78287-27-1

7-ethylcamptothecin

7-ethyl-14-nitro-camptothecin
1258494-58-4

7-ethyl-14-nitro-camptothecin

Conditions
ConditionsYield
With nitric acid; acetic anhydride at 0℃; for 1h;63.4%
7-ethylcamptothecin
78287-27-1

7-ethylcamptothecin

biotin
58-85-5

biotin

biotin-(20s)-7-ethylcamptothecin

biotin-(20s)-7-ethylcamptothecin

Conditions
ConditionsYield
With dmap; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 48h; Inert atmosphere;57%
7-ethylcamptothecin
78287-27-1

7-ethylcamptothecin

N-(+)-biotinyl-6-aminocaproic acid
72040-64-3

N-(+)-biotinyl-6-aminocaproic acid

6-biotinylaminocaproic acid-(20s)-7-ethylcamptothecin

6-biotinylaminocaproic acid-(20s)-7-ethylcamptothecin

Conditions
ConditionsYield
With dmap; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 48h; Inert atmosphere;56%
C17H20N2O4S2

C17H20N2O4S2

C28H29ClNO2(1+)*I(1-)

C28H29ClNO2(1+)*I(1-)

7-ethylcamptothecin
78287-27-1

7-ethylcamptothecin

C69H65ClN5O13S2(1+)*I(1-)

C69H65ClN5O13S2(1+)*I(1-)

Conditions
ConditionsYield
Stage #1: C17H20N2O4S2 With pyridine In tetrahydrofuran for 0.0833333h; Inert atmosphere; Cooling with ice;
Stage #2: With trichloromethyl chloroformate In tetrahydrofuran for 1h;
Stage #3: C28H29ClNO2(1+)*I(1-); 7-ethylcamptothecin With dmap; triethylamine In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; Cooling with ice;
31%
7-ethylcamptothecin
78287-27-1

7-ethylcamptothecin

12-Ethyl-8-methyl-7-propionyl-11H-indolizino[1,2-b]quinolin-9-one
152266-83-6

12-Ethyl-8-methyl-7-propionyl-11H-indolizino[1,2-b]quinolin-9-one

Conditions
ConditionsYield
With sodium azide; 18-crown-6 ether In N,N-dimethyl-formamide at 120℃; for 4h;20%
7-ethylcamptothecin
78287-27-1

7-ethylcamptothecin

(S)-2-(12-Ethyl-8-hydroxymethyl-9-oxo-9,11-dihydro-indolizino[1,2-b]quinolin-7-yl)-2-hydroxy-butyric acid hydrazide
1026285-00-6

(S)-2-(12-Ethyl-8-hydroxymethyl-9-oxo-9,11-dihydro-indolizino[1,2-b]quinolin-7-yl)-2-hydroxy-butyric acid hydrazide

Conditions
ConditionsYield
With hydrazine hydrate for 0.5h; Ambient temperature;

78287-27-1Downstream Products

78287-27-1Relevant articles and documents

Two novel camptothecin derivatives inhibit colorectal cancer proliferation via induction of cell cycle arrest and apoptosis in vitro and in vivo

Du, Hongzhi,Huang, Yue,Hou, Xiaoying,Quan, Xingping,Jiang, Jingwei,Wei, Xiaohui,Liu, Yang,Li, Hongyang,Wang, Puhai,Zhan, Meixiao,Ai, Xun,Lu, Ligong,Yuan, Shengtao,Sun, Li

, p. 546 - 559 (2018)

At present, chemotherapy is still to be the preferred and most significant therapeutic strategy for cancer patients in clinical practice. Although Camptothecin (CPT) has been discovered for over half century, a series of CPT derivatives such as Topotecan (TPT) and irinotecan (CPT-11) have been approved and are still to be the first-line medicines for clinical application. Up to now, the topoisomerase 1 inhibitor continues to be a significant drug development research field. Based on previous study of the structure-activity relationship, we consider that the introduction of lipophilic group at C7 position can prolong the retention time and the hydroxyl esterification at C20 can eliminate the hydrogen bond interaction, stabilize the E-lactone form and promote the anti-cancer effect. In this study, we carried out an optimization at C7 and C20 positions to afford two CPT derivatives 3g and 3j. Firstly, we predicted the possibly binding sites of two compounds with topoisomerase 1 by molecular docking. Then we evaluated the anti-proliferation effect of the two novel derivatives and compared the IC50 with CPT-11. Furthermore, the induction of cell cycle arrest and apoptosis was explored through karyomorphology, flow cytometry (FCM) and Western blot analysis. At last, we evaluated the anti-cancer effect and detected the mechanism in colorectal cancer xenograft model. In brief, all the data showed that the novel CPT derivatives (3g and 3j) could inhibit colorectal cancer proliferation via induction of cell cycle arrest and apoptosis in vitro and in vivo. It suggested that the two agents may be a new potential therapeutic strategy in the future.

Irinotecan Hydrochloride impurity as well as synthesis method and application thereof

-

Paragraph 0031; 0039; 0043; 0044, (2018/09/21)

The invention discloses an irinotecan Hydrochloride impurity which has a structural formula (1) as shown in the specification. In addition, the invention discloses a synthesis method and application of the impurity. The impurity is novel in structure and beneficial to quality control on an irinotecan Hydrochloride raw material medicine, and meanwhile, the synthesis method of the impurity has the characteristics of being simple in operation, an obtained sample is relatively high in purity and can be applied to control group study, and the like.

A new strategy to improve the metabolic stability of lactone: Discovery of (20 S,21 S)-21-fluorocamptothecins as novel, hydrolytically stable topoisomerase i inhibitors

Miao, Zhenyuan,Zhu, Lingjian,Dong, Guoqiang,Zhuang, Chunlin,Wu, Yuelin,Wang, Shengzheng,Guo, Zizao,Liu, Yang,Wu, Shanchao,Zhu, Shiping,Fang, Kun,Yao, Jianzhong,Li, Jian,Sheng, Chunquan,Zhang, Wannian

supporting information, p. 7902 - 7910 (2013/11/06)

Lactone is a common structural motif in biologically active natural products. However, the metabolic instability of lactone significantly reduces their in vivo potency. In the present investigation, a new strategy to improve the metabolic stability of lactone was provided by the design of α-fluoro ether as a novel bioisostere of lactone. The effectiveness of the α-fluoro ether/lactone replacement was validated by the discovery of (20S,21S)-21-fluorocamptothecins as hydrolytically stable topoisomerase I inhibitors. A highly potent camptothecin derivative, 8l, was successfully identified, which showed excellent in vitro and in vivo antitumor activities and represents a promising lead for the discovery of novel antitumor agents. Interestingly, this study also provided a new structure-activity relationship for the C21-carbonyl group of camptothecin, which has been regarded as an essential pharmacophore. Our results revealed that the conserved C21-carbonyl group can be replaced by a fluorine substituent. α-Fluoro ether may have general application in improving the metabolic stability of lactone.

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