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ChemicalBook > Product Catalog >Pharmaceutical intermediates >Bulk Drug Intermediates > (S)-4-Ethyl-4-hydroxy-7,8-dihydro-1h-pyrano[3,4-f]indolizine-3,6,10(4h)-trione

(S)-4-Ethyl-4-hydroxy-7,8-dihydro-1h-pyrano[3,4-f]indolizine-3,6,10(4h)-trione

(S)-4-Ethyl-4-hydroxy-7,8-dihydro-1h-pyrano[3,4-f]indolizine-3,6,10(4h)-trione Structure
CAS No.
110351-94-5
Chemical Name:
(S)-4-Ethyl-4-hydroxy-7,8-dihydro-1h-pyrano[3,4-f]indolizine-3,6,10(4h)-trione
Synonyms
(4S)-4-Ethyl-4-hydroxy-7,8-dihydro-1H-pyrano[3,4-f]indolizine-3,6,10-trione;(S)-4-hydroxy-4-propyl-7,8-dihydro-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione;RUBI-006;(S)-trione;10(4H)-TRIONE;4-F]INDOLIZINE-3;Trihydroxy lactone;Exatecan Impurity 3;8-DIHYDRO-1H-PYRANO[3;Exatecan intermediates
CBNumber:
CB41009288
Molecular Formula:
C13H13NO5
Molecular Weight:
263.25
MOL File:
110351-94-5.mol
Modify Date:
2024/7/2 8:55:07
Request For Quotation

(S)-4-Ethyl-4-hydroxy-7,8-dihydro-1h-pyrano[3,4-f]indolizine-3,6,10(4h)-trione Properties

Melting point 183-185℃ (decomposition)
Boiling point 666.6±55.0 °C(Predicted)
Density 1.50±0.1 g/cm3(Predicted)
storage temp. 2-8°C
pka 11.20±0.20(Predicted)
form Solid
color Off-white to light brown
InChI InChI=1S/C13H13NO5/c1-2-13(18)8-5-9-10(15)3-4-14(9)11(16)7(8)6-19-12(13)17/h5,18H,2-4,6H2,1H3/t13-/m0/s1
InChIKey IGKWOGMVAOYVSJ-ZDUSSCGKSA-N
SMILES C1(=O)C2N(C(=O)C3COC(=O)[C@@](CC)(O)C=3C=2)CC1

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H319-H302
Precautionary statements  P264-P280-P305+P351+P338-P337+P313P-P264-P270-P301+P312-P330-P501
HazardClass  IRRITANT

(S)-4-Ethyl-4-hydroxy-7,8-dihydro-1h-pyrano[3,4-f]indolizine-3,6,10(4h)-trione Chemical Properties,Uses,Production

Chemical Properties

Light yellow solid.

Uses

(4S)-4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione is a key intermediate in the synthesis of Irinotecan (I767500) and Camptothecin (C175150) analogs.

Application

(S)-4-Ethyl-4-hydroxy-7,8-dihydro-1h-pyrano[3,4-f]indolizine-3,6,10(4h)-trione is the key intermediate for the synthesis of a series of (20S)-camptothecin analogues. Since its isolation from the Chinese plant Camptothecaacuminata by Wall et al. In 1966, (20S)-camptothecin, a pent acyclic natural alkaloid, has re-emerged as one of the most important lead compounds for the discovery of new and selective anticancer drugs because of the disclosure of its unique mechanism of action as a selective inhibitor DNA topoisomerase Ⅰ, a process causing irreversible DNA damage and subsequent cell death. Three camptothecin derivatives with high antitumor activity, topotecan, belotecan, and irinotecan, have been launched as anticancer drugs in clinical practice, and many other analogues are at various stages of clinical development.

Preparation

Synthesis of (S)-4-Ethyl-4-hydroxy-7,8-dihydro-1h-pyrano[3,4-f]indolizine-3,6,10(4h)-trione: Compound (Formula 4) 4.3 g (100 mmol), 200 ml of dichloromethane, 200 ml of 2M sulfuric acid, stirred at room temperature for 2 h, separated the organic layer, washed with saturated brine, dried, recovered dichloromethane to dryness, and recrystallized from isopropanol to obtain S-tricyclic lactone (Formula 1) 1.5 g, mp 172-174°C, [α]D15+115.6° (C=0.5, chloroform), yield 57%.
Synthesis of (S)-4-Ethyl-4-hydroxy-7,8-dihydro-1h-pyrano[3,4-f]indolizine-3,6,10(4h)-trione

Clinical claims and research

Camptothecin is a pentacyclic alkaloid extracted from Camptotheca by Wall et al. in the early 1960s. As an anticancer chemical, the compound has quickly attracted people's attention due to its strong inhibitory activity against leukemia and various other malignant tumors in animal experiments. In the total synthesis of camptothecin, The total synthesis of (S)-4-Ethyl-4-hydroxy-7,8-dihydro-1h-pyrano[3,4-f]indolizine-3,6,10(4h)-trione is research focus.

(S)-4-Ethyl-4-hydroxy-7,8-dihydro-1h-pyrano[3,4-f]indolizine-3,6,10(4h)-trione Preparation Products And Raw materials

Raw materials

(S)-4-Ethyl-4,6-dihydroxy-3,10-dioxo-3,4,8,10-tetrahydro-1H-pyrano[3,4-f]indolizine-7-carboxylic acid tert-butyl ester CHUGAI-01 (4'S)-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

Preparation Products

(S)-4-Ethyl-4-hydroxy-7,8-dihydro-1h-pyrano[3,4-f]indolizine-3,6,10(4h)-trione Suppliers

Global( 220)Suppliers
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BTC pharm India +918790379245 AndhraPradesh, India 1269 58 Inquiry
R SCIENTIFIC +919000280374 Hyderabad, India 143 58 Inquiry
VGS SYNTHESIS PRIVATE LIMITED +91-9866975588 +91-9866975588 Hyderabad, India 1818 58 Inquiry
Avra Laboratories Pvt Ltd +91-8008572391 +91-8008572391 Hyderabad, India 43 58 Inquiry
Venkatasai Life Sciences +91-9908134868 +91-8008303069 Hyderabad, India 186 58 Inquiry
ALS INDIA LIFE SCIENCES +91-8977036379 +91-8977036379 Hyderabad, India 1879 58 Inquiry
Pharmaffiliates Analytics and Synthetics P. Ltd +91-172-5066494 Haryana, India 6773 58 Inquiry
A.J Chemicals 91-9810153283 New Delhi, India 6124 58 Inquiry
CLEARSYNTH LABS LTD. +91-22-45045900 Hyderabad, India 6351 58 Inquiry
Amadis Chemical Company Limited 571-89925085 China 131980 58 Inquiry
Supplier Advantage
BTC pharm India 58
R SCIENTIFIC 58
VGS SYNTHESIS PRIVATE LIMITED 58
Avra Laboratories Pvt Ltd 58
Venkatasai Life Sciences 58
ALS INDIA LIFE SCIENCES 58
Pharmaffiliates Analytics and Synthetics P. Ltd 58
A.J Chemicals 58
CLEARSYNTH LABS LTD. 58
Amadis Chemical Company Limited 58

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(S)-4-ETHYL-4-HYDROXY-7,8-DIHYDRO-1H-PYRANO[3,4-F]INDOLIZINE-3,6,10(4H)-TRIONE (s)-8-Ethyl-8-hydroxy-2,3,5,8-tetrahydro-6-oxa-3a-aza-cyclopenta[b]naphthalene-1,4,7-trione (S)-4-hydroxy-4-propyl-7,8-dihydro-1H-pyrano[3,4-f]indolizine-3 (S)-4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione 1H-Pyrano[3,4-f]indolizine-3,6,10(4H)-trione, 4-ethyl-7,8-dihydro-4-hydroxy-, (4S)- 1H-Pyrano[3,4-f]indolizine-3,6,10(4H)-trione, 4-ethyl-7,8-dihydro-4-hydroxy-, (S)- RUBI-006 (S)-4-ETHYL-4-HYDROXY-7,8-DIHYDRO-1H-PYRANO[3,4-F]INDOLIZINE-3,6,10(4H)-TRIONE 110351-94-5 (S)-trione (S)-4-ETHYL-4-HYDROXY-7 10(4H)-TRIONE 4-F]INDOLIZINE-3 8-DIHYDRO-1H-PYRANO[3 Exatecan intermediates (4S)-4-Ethyl-4-hydroxy-7,8-dihydro-1H-pyrano[3,4-f]indolizine-3,6,10-trione (S)-4-hydroxy-4-propyl-7,8-dihydro-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione Trihydroxy lactone Exatecan Intermediate 1 (S)-4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolidin-3,6,10(4H)-trione Exatecan Impurity 3 (S) 4-ethyl-4-hydroxy-7,8-dihydro-1H-pyrano O [3,4-F] indoleazine-3,6,10 (4) - one Irinotecan Impurity 64 110351-94-5 Anti-cancer ADCs Linkers 1