CAS: 108212-75-5; S-((2R,3S,4S,6S)-6-((((2R,3S,4S,5R,6R)-5-(((2S,4S,5S)-5-(Ethylamino)-4-Methoxytetrahydro-2H-Pyran-2-yl)Oxy)-4-Hydroxy-6-(((2S,5Z,9R,13E)-9-Hydroxy-12-((Methoxycarbonyl)Amino)-13-(2-(Methyltrisulfaneyl)Ethylidene)-11-Oxobicyclo[7.3.1]Trideca-1(12),5-Dien-3

该化合物是来自细菌微微莫诺斯波拉脑细胞的强效抗突脉冲抗生素,它属于亚尼恩化合物,众所周知,该化合物具有诱发DNA线断裂的能力,导致快速分裂细胞产生细胞毒性效应.该化合物展示了一种复杂的结构,其特点是独特的双环核,其中包括高度反应性二硝基乙基细胞,这对它的行动机制至关重要.卡利切米辛1I因其选择癌症细胞而特别突出,使它成为定向癌症治疗的对象.该化合物具有很强的毒性,需要在临床环境中进行谨慎处理和管理.该化合物在抗体-药物共生素中的潜在用途已经进行了研究,可以与专门针对肿瘤细胞的抗体联系起来,从而提高治疗效率,同时尽量减少对正常组织造成的伤害.

结构式图片

欧盟法规

C&L通报

上下游产品

CAS号144668-44-0 | CAS号158862-55-6 | CAS号74-93-1 甲硫醇 | CAS号624-92-0 二甲基二硫醚 | CAS号122470-58-0 S-[(2R,3S,4S,6S... | CAS号3878-45-3 三苯基膦硫 | CAS号791-28-6 三苯基氧化膦

合成工艺路线路线简述

  • 合成目标产物 Calicheamicin 主要起始原料 Carbamic Acid, [8-[[4,6-Dideoxy-4-[[[2,6-Dideoxy-4-S-[4-[(6-Deoxy-3-O-Methyl-α-L-Mannopyranosyl)Oxy]-3-Iodo-5,6-Dimethoxy-2-Methylbenzoyl]-4-Thio-β-D-Ribo-Hexopyranosyl]Oxy]Amino]-2-O-[2,4-Dideoxy-4-[ethyl[(9H-Fluoren-9-Ylmethoxy)Carbonyl]Amino]-3-O-Methyl-α-L-Threo-Pentopyranosyl]-β-D-Glucopyranosyl]Oxy]-1-Hydroxy-13-[2-(Methyltrithio)Ethylidene]-11-Oxobicyclo[7.3.1]Trideca-4,9-Diene-2,6-Diyn-10-Yl]-, Methyl Ester, [1R-(1R*,4Z,8S*,13E)]-
  • (文献来源)合成步骤主要原料 Carbamic Acid, [8-[[4,6-Dideoxy-4-[[[2,6-Dideoxy-4-S-[4-[(6-Deoxy-3-O-Methyl-α-L-Mannopyranosyl)Oxy]-3-Iodo-5,6-Dimethoxy-2-Methylbenzoyl]-4-Thio-β-D-Ribo-Hexopyranosyl]Oxy]Amino]-2-O-[2,4-Dideoxy-4-[ethyl[(9H-Fluoren-9-Ylmethoxy)Carbonyl]Amino]-3-O-Methyl-α-L-Threo-Pentopyranosyl]-β-D-Glucopyranosyl]Oxy]-1-Hydroxy-13-[2-(Methyltrithio)Ethylidene]-11-Oxobicyclo[7.3.1]Trideca-4,9-Diene-2,6-Diyn-10-Yl]-, Methyl Ester, [1R-(1R*,4Z,8S*,13E)]-
在 Camphor-10-Sulfonic Acid,四丁基氟化铵体系中,化学反应生成卡利奇霉素
参考文献:Hitchcock,Stephen A.; Chu-Moyer,Margaret Y.; Boyer,Serge H.,Journal Of The American Chemical Society,1995,Vol. 117,# 21,P. 5750-5756
标题:Hitchcock,Stephen A.; Chu-Moyer,Margaret Y.; Boyer,Serge H.,Journal Of The American Chemical Society,1995,Vol. 117,# 21,P. 5750-5756

专利信息


专利号:US-5442065-A
优先权日:1993-09-09
标 题:Synthesis of tetrahydroquinoline enediyne core analogs of dynemicin
发明人:MAGNUS PHILIP D; ILIADIS THEODORE; EISENBEIS SHANE A; FAIRHURST ROBIN A
权利人:UNIV TEXAS
摘要:A process is described for the preparation of the core azobicyclo[7.3.1]tridecaenediyne moiety of the antitumor antibiotic dynemicin. The synthesis allows efficient production of the enediyne as a stable, compound in good yield from the adamantyl N-protected azabicyclo[7.3.1]tridecadiyne. The adamantyl protecting group is employed in the starting material, N-adamantyl dihydroquinoline or N-adamantyl 6-methoxy quinoline. Also disclosed are process for the synthesis of 3-hydroxy-6-methoxyquinoline and several N-substituted derivatives of azobicyclo[7.3.1]tridecaenediyne. Solid tumor and leukemia assays were performed on the analogs of dynemicin. The results suggest a method that these compounds will useful in treating certain types of leukemias and solid tumors. The disclosed synthesis provides a route to new dynemicin intermediates and analogs which will allow development of second and third generation dynemicins.

专利号:WO-2017100796-A1
优先权日:2015-12-11
标 题 :Modulation of globoseries glycosphingolipid synthesis and cancer biomarkers
发明人:WONG CHI-HUEY; HSU TSUI-LING; WU CHUNG-YI; CHEUNG SARAH K C; CHUANG PO-KAI
权利人:SINACA ACAD; WONG CHI-HUEY; HSU TSUI-LING
摘要:The present disclosure relates to methods and compositions which can modulate the globoseries glycosphingolipid synthesis. Particularly, the present disclosure is directed to glycoenzyme inhibitor compound and compositions and methods of use thereof that can modulate the synthesis of globoseries glycosphingolipid SSEA-3/SSEA-4/GloboH in the biosynthetic pathway; particularly, the glycoenzyme inhibitors target the alpha-4GalT; beta- 4GalNAcT-I; or beta-3GalT-V enzymes in the globoseries synthetic pathway. Additionally, the present disclosure is also directed to vaccines, antibodies, and/or immunogenic conjugate compositions targeting the SSEA-3/SSEA-4/GLOBO H associated epitopes (natural and modified) which elicit antibodies and/or binding fragment production useful for modulating the globoseries glycosphingolipid synthesis. Moreover, the present disclosure is also directed to the method of using the compositions described herein for the treatment or detection of hyperproliferative diseases and/or conditions. Furthermore, the instant disclosure also relates to cancer stem cell biomarkers for disgnostic and therapeutic uses.

专利号:US-10342858-B2
优先权日:2015-01-24
标题 :Glycan conjugates and methods of use thereof
发明人:WONG CHI-HUEY; WU CHUNG-YI
权利人:ACADEMIA SINICA
摘要:The present disclosure is directed to vaccines, antibodies, and/or immunogenic conjugate compositions targeting the SSEA3/SSEA4/GloboH associated epitopes (natural and modified) which elicit antibodies and/or binding fragment production useful for modulating the globo-series glycosphingolipid synthesis. The present disclosure relates to methods and compositions which can modulate the globo-series glycosphingolipid synthesis. Particularly, the present disclosure is directed to glycoenzyme inhibitor compound and compositions and methods of use thereof that can modulate the synthesis of globo-series glycosphingolipid SSEA3/SSEA4/GloboH in the biosynthetic pathway; particularly, the glycoenzyme inhibitors target the alpha-4GalT; beta-4GalNAcT-I; or beta-3GalT-V enzymes in the globo-series synthetic pathway. Moreover, the present disclosure is also directed to the method of using the compositions described herein for the treatment or detection of hyperproliferative diseases and/or conditions.

专利号:US-10590158-B2
优先权日:2015-06-29
标题:Total synthesis of shishijimicin A and analogs thereof
发明人:NICOLAOU KYRIACOS C; LI RUOFAN; LU ZHAOYONG; SOHN TE-IK; WOODS JAMES; PITSINOS EMMANOUIL N
权利人:UNIV RICE WILLIAM M
摘要:In one aspect, the present disclosure provides shishijimicin analogs of the formula: wherein the variables are as defined herein. In another aspect, the present disclosure also provides methods of preparing the compounds disclosed herein. In another aspect, the present disclosure also provides pharmaceutical compositions and methods of use of the compounds disclosed herein. Additionally, antibody drug conjugates of the compounds are also provided.

专利号:US-11465997-B2
优先权日:2017-06-22
标 题 :Synthesis of disorazoles and analogs thereof as potent anticancer agents
发明人:NICOLAOU KYRIACOS C; BELLAVANCE GABRIEL; BUCHMAN MAREK; PULUKURI KIRAN KUMAR; RIGOL STEPHAN
权利人:UNIV RICE WILLIAM M
摘要:In one aspect, the present disclosure provides disorazole analogs of the formula: Formula (I) wherein the variables are as defined herein. In another aspect, the present disclosure also provides methods of preparing the compounds disclosed herein. In another aspect, the present disclosure also provides pharmaceutical compositions and methods of use of the compounds disclosed herein. Additionally, drug conjugates with cell targeting moieties of the compounds are also provided.

专利号:US-7473797-B2
优先权日:2004-04-27
标 题 :Methods of 1,3-enyne preparation using copper (I) catalysts
发明人:VENKATARAMAN DHANDAPANI; BATES CRAIG G; SAEJUENG PRANORM
权利人:UNIV MASSACHUSETTS
摘要:A copper(I) bi-dentate ligand complex-catalyzed procedure for synthesis of 1,3-enynes. The methods and/or systems of this invention afford a variety of enynes, tolerate a variety of sensitive functional groups, and can be employed without resort to expensive palladium reagents.
台州市科瑞生物技术有限公司
⚠️ 未注册 · 未认证企业
⚠️ 该商家尚未完成注册及企业认证,请用户仔细辨别,谨慎交易。
数据来源于公开网络搜索,平台未作核实,请自行辨别。
🏢敬请 企业认领
🏬开设公司展台
📢获取免费会员权益
🎖️点亮专属注册企业标签
📇展现公司完整信息 样本查看立即注册认领 →
网址: http://www.pharm-intermediates.com
企业联系电话:0576-88813233👤
📞台州市科瑞生物技术有限公司 ⚠️参考联系方式
联系人:金崇光
电话:0576-88813233
手机:13396860566
传真:0576-88813233
邮箱:sales@pharm-intermediates.com
通信地址: 台州市开发大道东段288号
邮编: 318000
🆔 联系时候可告知是从"百琢研"平台获取的信息.
⚠️ 声明: 该企业未认证、未认领,请自行辨别信息的真实性和可靠性。咨询或交易时请注意风险评估与信息核实,百琢研不参与任何交易。企业认领注册入口→

地址:台州市开发大道东段288号
⚠️ 未注册 · 未认证企业
注册入口 备注: 📌 数据来源说明:本展台内容基于各搜索引擎等公开数据整理,仅作展示用途。请用户自行辨别
✉️ 若企业需抹除展台内容或有异议, 请通过页面底部联系方式告知我们,我们会尽快处理。
第 1 / 1 页

供应商参考报价(招募中)

品牌试剂参考报价(招募中)

📌 第三方产品分析报告

✅ COA系统入驻 | 共享模式

主要参考文献


1: Singh S, Michalska K, Bigelow L, Endres M, Kharel MK, Babnigg G, Yennamalli RM, Bingman CA, Joachimiak A, Thorson JS, Phillips GN Jr. Structural Characterization of CalS8, a TDP-α-D-Glucose Dehydrogenase Involved in Calicheamicin Aminodideoxypentose Biosynthesis. J Biol Chem. 2015 Oct 23;290(43):26249-58. doi: 10.1074/jbc.M115.673459. Epub 2015 Aug 3.
2: Tsodikov OV, Hou C, Walsh CT, Garneau-Tsodikova S. Crystal structure of O-methyltransferase CalO6 from the calicheamicin biosynthetic pathway: a case of challenging structure determination at low resolution. BMC Struct Biol. 2015 Jul 15;15:13. doi: 10.1186/s12900-015-0040-6.
3: Damelin M, Bankovich A, Park A, Aguilar J, Anderson W, Santaguida M, Aujay M, Fong S, Khandke K, Pulito V, Ernstoff E, Escarpe P, Bernstein J, Pysz M, Zhong W, Upeslacis E, Lucas J, Lucas J, Nichols T, Loving K, Foord O, Hampl J, Stull R, Barletta F, Falahatpisheh H, Sapra P, Gerber HP, Dylla SJ. Anti-EFNA4 Calicheamicin Conjugates Effectively Target Triple-Negative Breast and Ovarian Tumor-Initiating Cells to Result in Sustained Tumor Regressions. Clin Cancer Res. 2015 Sep 15;21(18):4165-73. doi: 10.1158/1078-0432.CCR-15-0695. Epub 2015 May 26. doi: 10.1002/bip.22591. doi: 10.1002/cbic.201402489. Epub 2014 Nov 17. doi: 10.1002/cbic.201402119.

合成参考文献


参考文献:10.1006/jmbi.1996.0718
摘要:Kumar RA, Ikemoto N, Patel DJ. Solution structure of the calicheamicin gamma 1I-DNA complex. J Mol Biol. 1997 Jan 17;265(2):187–201. doi: 10.1006/jmbi.1996.0718.
📝 需求与反馈
尽可能描述清楚需求与问题信息
×

通知