130144-34-2

Basic information

• Product Name: 1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 4,11-diethyl-4,9-dihydroxy-
• Synonyms: 7-Ethyl-10-hydroxycamptothecin;4,11-Diethyl-4,9-dihydroxy-1H-pyrano[3,4:6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
• CAS NO: 130144-34-2
• Molecular Formula: C₂₂H₂₀N₂O₅
• Molecular Weight: 392.4
• Mol File: 130144-34-2.mol
• Article Data: 46

Chemical Properties

• Boiling Point: 810.3±65.0 °C(Predicted)
• Appearance: /
• Density: 1.51
• Refractive Index: 1.776
• PKA: 9.13±0.40(Predicted)
• CAS DataBase Reference: 1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 4,11-diethyl-4,9-dihydroxy-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 4,11-diethyl-4,9-dihydroxy-(130144-34-2)
• EPA Substance Registry System: 1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 4,11-diethyl-4,9-dihydroxy-(130144-34-2)

Safety Data

• Hazardous Substances Data: 130144-34-2(Hazardous Substances Data)

Usage

General Description

1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 4,11-diethyl-4,9-dihydroxy- is a chemical compound with a complex molecular structure. It contains a pyranoindolizinoquinoline core with a dione functional group and two side chains consisting of ethyl and hydroxy groups. 1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 4,11-diethyl-4,9-dihydroxy- may have potential biological or pharmaceutical applications due to its unique structure and functional groups. Further research and testing may be required to determine its specific properties and potential uses.

InChI:InChI=1/C20H16N2O5/c1-2-20(26)13-7-15-17-10(6-11-14(21-17)4-3-5-16(11)23)8-22(15)18(24)12(13)9-27-19(20)25/h3-7,23,26H,2,8-9H2,1H3/t20-/m0/s1

Upstream product

• 97682-44-5 irinotecan 
• 924648-17-9 1-(5-fluoro-2-nitrophenyl)propan-1-one 
• 453518-19-9 1-(5-hydroxy-2-nitrophenyl)propan-1-one 
• 456-48-4 3-Fluorobenzaldehyde 
• 458-02-6 3-fluorobenzaldehyde oxime 
• 403-54-3 m-Fluorobenzonitrile 
• 455-67-4 1-(3-fluorophenyl)propan-1-one 
• 145474-12-0 4-carbomethoxy-7-oxo-de-AB-deoxycamptothecin 
• 145474-19-7 5-methoxy-2-nitrophenyl vinyl ketone 
• 36625-47-5 methyl α-(tetrahydro-2-pyrrolidinylidene)acetate 
• 60997-56-0 2'-amino-5'-methoxypropiophenone 
• 120461-65-6 dimethyl 3-chloro-2-pentenedioate 
• 20357-24-8 5-methoxy-2-nitro-benzaldehyde 
• 1026799-43-8 7-ethyl-10-hydroxy-20-deoxycamptothecin 

Downstream Products

• 100286-90-6 irinotecan hydrochloirde 
• 97682-44-5 irinotecan 
• 86639-52-3 7-ethyl-10-hydroxycamptothecin 
• 136572-09-3 irinotecan hydrochloride trihydrate 

Relevant articles and documents

On-Demand Activation of a Bioorthogonal Prodrug of SN-38 with Fast Reaction Kinetics and High Releasing Efficiency in Vivo

Although a myriad of bioorthogonal prodrugs have been developed, very few of them present both fast reaction kinetics and complete cleavage. Herein, we report a new bioorthogonal prodrug strategy with both fast reaction kinetics (k2: ～103 M-1 s-1) and complete cleavage (>90% within minutes) using the bioorthogonal reaction pair of N-oxide and boron reagent. Distinctively, an innovative 1,6-elimination-based self-immolative linker is masked by N-oxide, which can be bioorthogonally demasked by a boron reagent for the release of both amino and hydroxy-containing payload in live cells. Such a strategy was applied to prepare a bioorthogonal prodrug for a camptothecin derivative, SN-38, resulting in 10-fold weakened cytotoxicity against A549 cells, 300-fold enhanced water solubility, and on-demand activation upon a click reaction both in vitro and in vivo. This novel bioorthogonal prodrug strategy presents significant advances over the existing ones and may find wide applications in drug delivery in the future.

A stable and cleavable o-linked spacer for drug delivery systems

Anti-cancer chemotherapy with good efficacy and fewer side effects is highly desirable. A drug delivery system comprising a cancer-targeting module and a cytotoxic agent connected with a cleavable linker is promising for reducing side effects. The development of a cleavable linker satisfying the requirements of both stability and cleavability, however, is difficult, especially when a carbonate moiety is used for conjugating the linker to a hydroxy group in a drug of interest. We herein report a new stable linker comprising carbamate and ester spacers, which can be introduced on a hydroxy group of a drug. This linker is more stable in aqueous neutral buffer than a corresponding carbonate-type linker, and releases a payload anti-cancer drug, SN-38, through a two-step sequence upon cathepsin B treatment. This linker may have potential use in other drug delivery systems to lower side effects by selectively transporting cytotoxic drugs to tumor cells.

A preparation method of irinotecan hydrochloride (by machine translation)

The invention relates to a preparation method of irinotecan hydrochloride. Its steps are: parent ring to camptothecin as raw material generated by the reaction with the aldehyde 7 - ethyl camptothecin; hydrogen peroxide oxidation then N - oxide - 7 - ethyl camptothecin; by the illumination rearrangement 7 - ethyl - 10 - hydroxy camptothecin; 4 - piperidyl with dimethyl carbonate reaction to produce 4 - piperidyl carbonic acid methyl ester; 7 - ethyl - 10 - hydroxy camptothecin with 4 - piperidyl carbonic acid methyl ester reaction generating irinotecan monomer; irinotecan monomers with hydrochloric salt to obtain the finished product of the irinotecan hydrochloride. Compared with the prior art, the present invention avoid the use of phosgene in the reaction process, chloroform poisonous substance, in production with safe, convenient, less pollution and the like; in addition, the synthetic method avoids the need of the prior process in the defects of the chromatographic column separation and purification, reduces the production cost of the irinotecan, has great economic benefit. (by machine translation)