CAS: 20830-81-3; (8S,10S)-8-Acetyl-10-(((2R,4S,5S,6S)-4-Amino-5-Hydroxy-6-Methyltetrahydro-2H-Pyran-2-yl)Oxy)-6,8,11-Trihydroxy-1-Methoxy-7,8,9,10-Tetrahydrotetracene-5,12-Dione

上下游产品

-6a,7,8,9,10,10a-hexahydro-5,8,12-trihydroxy-1-methoxy-6,11-naphthacenedione(8S-cis)-8-acetyl-10-(3-amino-2,3,6-trideoxy-α-L-lyxohexopyranosyl)oxy-6a,7,8,9,10,10a-hexahydro-5,8,12-trihydroxy-1-methoxy-6,11-naphthacenedione (S)-2-Amino-4-methyl-pentanoic acid [(2S,3S,4S,6R)-6-((1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-3-hydroxy-2-methyl-tetrahydro-pyran-4-yl]-amide N-[4-(daunorubicin-N-carbonyloxymethyl)phenyl] O-β-D-glucopyranosyl carbamate N-[4-(daunorubicin-N-carbonyloxymethyl)phenyl] O-β-D-galactopyranosyl carbamate3'-N-acetyldaunorubicin 3'-N-trifluoroacetyldaunorubicin (+)-Daunomycinone 3-acetyl-3,5,12-trihydroxy-1-[5-hydroxy-4-(4-hydroxyphenylamin°Carbonylamino)-6-methylperhydro-2-pyranoloxy]-10-methoxy-(1S,3S)-1,2,3,4,6,11-hexahydro-6,11-naphthacenedione

N-[4-(Daunorubicin-N-Carbonyloxymethyl)Phenyl] O-β-D-Glucopyranosyl Carbamate置于bovine Liver β-Galactosidase,水体系中,化学反应生成道诺霉素
参考文献:Novel Anthracycline-Spacer-β-Glucuronide,-β-Glucoside,And-β-Galactoside Prodrugs For Application In Selective Chemotherapy
标题:Novel Anthracycline-Spacer-β-Glucuronide,-β-Glucoside,And-β-Galactoside Prodrugs For Application In Selective Chemotherapy
摘要:A Series Of Anthracycline Prodrugs Containing An Immolative Spacer Was Synthesized For Application In Selective Chemotherapy. The Prodrugs Having The General Structure Anthracycline-Spacer-Beta-Glycoside Were Designed To Be Activated By Beta-Glucuronidase Or Beta-Galactosidase. Prodrugs With-Chloro,Bromo Or-N-Hexyl Substituents On The Spacer Were Synthesized As Well As Prodrugs Containing A-Beta-Glucuronyl,-Beta-Glucosyl Or-Beta-Galactosyl Carbamate Specifier. The Key Step In The Synthesis Of All Prodrugs Is The Highly Beta-Diastereoselective Addition Reaction Of The Anomeric Hydroxyl Of A Glycosyl Donor To A Spacer Isocyanate Resulting In The Respective Beta-Glycosyl Carbamate Pro-Moieties. The Resulting Protected Pro-Moieties Were Coupled To An Anthracycline. Prodrugs Were Evaluated With Respect To Activation Rate By The Appropriate Enzyme And Additionally,Their Ic50 Values Were Determined. Optimal Prodrugs In This Study Were At Least 100-To 200-Fold Less Toxic Than Their Corresponding Drug In Vitro And Were Activated To The Parent Drug In A Half-Life Time Of Approximately 2 H. (C) 1999 Elsevier Science Ltd. All Rights Reserved.
Doi:10.1016/s0968-0896(99)00095-4

专利信息

专利号:US-4288608-A
优先权日:1978-06-01
标题:Synthesis of anthracyclines
发明人：JOHNSON FRANCIS; KIM KYOUNG S
权利人:RESEARCH CORP
摘要:There is provided a novel method of synthesizing certain heterocyclic quinones. In particular there is provided a novel and regiospecific synthesis of 9-acetyl-6,11-dihydroxy-4-methoxy-7,8,9,10-tetrahydronaphthacene-5,12-quinone (7,9-dideoxydaunomycinone) which is known intermediate in the synthesis of daunomycinone. There is also provided a method of preparing analogs of 7,9-dideoxydaunomycinone which thus provide for the preparation of known and desired analogs of daunomycinone. Daunomycinone is a known compound which is an intermediate in the preparation of the clinically accepted naturally-occurring antitumor antibiotics daunomycin and its derivitive adriamycin.

专利号:WO-2024104433-A9
优先权日:2022-11-16
标 题:Use of galectin-1 as immune checkpoint in preparation of tumor immunotherapy medicament and medicament
发明人：ZHANG YU; HONG YU; SI XIAOFANG; LIU WENJING; MAI XUEYING
权利人:NAT INSTITUTE OF BIOLOGICAL SCIENCES BEIJING
摘要:Provided are use of galectin-1 (Gal-1) as an immune checkpoint in the preparation of a tumor immunotherapy medicament and the medicament, and provided is a new tumor immunotherapy strategy targeting the new immune checkpoint. Lactose and a derivative thereof can inhibit the immune checkpoint by competing Gal-1 on the surfaces of a cancer cell and an immune cell, and do not have significant toxic and side effects. Knocking out B4GATL1 to reduce protein galactosylation can significantly reduce the level of Gal-1 transferred from a tumor to a T cell, thereby enhancing the activation and function of the T cell. In addition, a lactose synthetase component LALBA is overexpressed in a mouse tumor, and de novo synthesis of lactose in a tumor microenvironment can be realized, such that an immune response mediated by a CD8+ T cell is enhanced. In combination with the anti-tumor effect and economic cost of lactose, a wide and feasible idea is provided for cancer treatment.

专利号:US-2009227617-A1
优先权日:2008-03-07
标题:Esters Of Glucuronide Prodrugs Of Anthracyclines And Method Of Preparation And Use In Tumor-Selective Chemotherapy
发明人：ABEN RENE WILHELMUS MARIE; SCHEEREN JOHAN WILHELM; LAMBERTUS MARIA CORNELISSEN JE; DE VOS DICK; HAISMA HIDDE JACOB
权利人:PHARMACHEMIE BV
摘要:The invention relates to novel esters and in particular to some novel esters of glucuronide prodrugs of anthracyclines having tunable water-solubility, their synthesis and use in tumor-selective chemotherapy. It appeared that in the final step in the synthesis of these prodrugs, i.e. the coupling of the glucuronide spacer moiety to the parent drug molecule, protection of the sugar hydroxyls is, surprisingly, no longer required. A process for the preparation of these unprotected sugar spacer moieties is also disclosed.

专利号:US-10975069-B2
优先权日:2014-04-01
标 题 :Sigma-2 receptor ligand drug conjugates as antitumor compounds, methods of synthesis and uses thereof
发明人：HAWKINS WILLIAM; MACH ROBERT; SPITZER DIRK; VANGVERAVONG SUWANNA; VAN TINE BRIAN
权利人:UNIV WASHINGTON
摘要:Methods and compositions for treating cancers such as pancreatic cancer and synovial sarcoma are disclosed. Compounds comprising a sigma-2 receptor-binding moiety and a ferroptosis-inducing moiety are described, such as the methanesulfonate salt of a compound of structural Formula IV, n n, wherein n is an integer chosen from 1, 2, 3, 4, and 5, and R 2 is H or methyl. At least one described molecular species exhibits an IC 50 value below 5 μM against human pancreatic cancer cells in vitro. Administration of this species promoted shrinkage of pancreatic cancer tumors in a murine model system in vivo. It led to a 100% survival of experimental animals over a time course in which control therapies provided only 30% or 40% survival. Methods of synthesis of molecular species are also disclosed.

专利号:US-8846882-B2
优先权日:2011-04-29
标 题 :Method of producing 4-demethoxydaunorubicin
发明人：ZABUDKIN ALEXANDER; MATVIENKO VICTOR; MATVYEYEV ALEXEY
权利人:ZABUDKIN ALEXANDER; MATVIENKO VICTOR; MATVYEYEV ALEXEY; SYNBIAS PHARMA AG
摘要:The present invention relates to a method for the synthesis of 4-demethoxydaunorubicin (idarubicin) having the chemical structure of formula (I), which involves the demethylation of 3′-Prot-daunorubicin in the presence of a soft Lewis acid. The method of the present invention does not comprise cleavage of the glycosidic linkage at carbon C7, thus resulting in a faster synthesis cycle and an improved yield of the final product.

专利号:US-2022265691-A1
优先权日:2019-07-12
标 题 :Methods for use of gene expression as an indicator of e-selectin inhibitor efficacy and clinical outcome for multiple tumor types
发明人：MAGNANI JOHN L; FOGLER WILLIAM E; THACKRAY HELEN M; FELDMAN ERIC J; STEWART DAVID
权利人:GLYCOMIMETICS INC
摘要:Cancer patients that express high levels of the E-selectin ligand (sialyl Lea/x) on their tumors have a poorer outcome. Interestingly, relapsed/refractory acute myeloid leukemia (AML) patients expressing high levels of sialyl Lex on their blasts show the greatest therapeutic response when treated with the E-selection inhibitor compound of Formula I. Transcriptome profiling of E-selectin ligand-forming glycosylation genes showed that ST3GAL4 and FUT7 were consistently expressed in the majority of cancers evaluated. Poor survival outcomes of FLT3-mutated AML patients that express high levels of ST3GAL4 and FUT7 implicated E-selectin in this disease state. These genes may be predictive biomarkers in AML patients. Methods of treatment of cancer comprising screening AML patients for expression of genes that contribute to the synthesis of the E-selectin ligand sialyl Lex, then treating those patients with an E-selection inhibitor, are disclosed.