• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利：CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法，用中文像聊天一样搜索，搜遍4000万医学文献。AI智能推荐，让科研检索更轻松。

立即免费搜索

文件翻译

保留排版，准确专业，支持PDF/Word/PPT等文件格式，支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述，25分钟生成高质量综述，智能提取关键信息，辅助科研写作。

立即免费体验

多种取代的双吡咯里西啶/硫代吡咯里西啶氧化吲哚/苊并姜黄素类化合物的合成——顺序甲亚胺叶立德环加成反应

Synthesis of diversely substituted bis-pyrrolizidino/ thiopyrrolizidino oxindolo/acenaphthyleno curcuminoids sequential azomethine ylide cycloaddition.

作者信息

Singh Meenakshi, Hazra Abhijit, Bharitkar Yogesh P, Kalia Ritu, Sahoo Ashutosh, Saha Sneha, Ravichandiran V, Ghosh Shekhar, Mondal Nirup B

机构信息

National Institute of Pharmaceutical Education and Research (NIPER) (IICB Campus), 4, Raja S. C. Mullick Road, Jadavpur Kolkata - 700 032 India.

Department of Organic and Medicinal Chemistry, Indian Institute of Chemical Biology, Council of Scientific and Industrial Research 4, Raja S. C. Mullick Road, Jadavpur Kolkata - 700 032 India

出版信息

RSC Adv. 2018 May 23;8(34):18938-18951. doi: 10.1039/c8ra02725k. eCollection 2018 May 22.

DOI:10.1039/c8ra02725k
PMID:35539652
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9080697/
Abstract

Curcumin has been transformed to several diversely substituted bis-pyrrolizidino/thiopyrrolizidino oxindolo/acenaphthyleno curcuminoids a sequential azomethine ylide cycloaddition reaction using isatins/acenaphthoquinone and proline/thioproline as the reagents. The products were separated extensive chromatography and characterized by 1D/2D NMR and HRMS analysis.

摘要

姜黄素已通过使用异吲哚酮/苊醌和脯氨酸/硫代脯氨酸作为试剂的顺序甲亚胺叶立德环加成反应转化为几种不同取代的双吡咯里西啶/硫代吡咯里西啶氧化吲哚/苊并姜黄素类化合物。产物通过广泛的色谱法分离，并通过一维/二维核磁共振和高分辨质谱分析进行表征。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/74b0/9080697/03fdf75560af/c8ra02725k-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/74b0/9080697/c4c782386512/c8ra02725k-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/74b0/9080697/cb7a2559a31c/c8ra02725k-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/74b0/9080697/cd0f097530c2/c8ra02725k-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/74b0/9080697/6116e6a696fc/c8ra02725k-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/74b0/9080697/222935f79f27/c8ra02725k-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/74b0/9080697/fc57883171c5/c8ra02725k-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/74b0/9080697/03fdf75560af/c8ra02725k-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/74b0/9080697/c4c782386512/c8ra02725k-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/74b0/9080697/cb7a2559a31c/c8ra02725k-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/74b0/9080697/cd0f097530c2/c8ra02725k-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/74b0/9080697/6116e6a696fc/c8ra02725k-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/74b0/9080697/222935f79f27/c8ra02725k-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/74b0/9080697/fc57883171c5/c8ra02725k-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/74b0/9080697/03fdf75560af/c8ra02725k-f3.jpg

相似文献

1
Synthesis of diversely substituted bis-pyrrolizidino/ thiopyrrolizidino oxindolo/acenaphthyleno curcuminoids sequential azomethine ylide cycloaddition.多种取代的双吡咯里西啶/硫代吡咯里西啶氧化吲哚/苊并姜黄素类化合物的合成——顺序甲亚胺叶立德环加成反应
RSC Adv. 2018 May 23;8(34):18938-18951. doi: 10.1039/c8ra02725k. eCollection 2018 May 22.
2
Semisynthesis of Novel Dispiro-pyrrolizidino/thiopyrrolizidino-oxindolo/indanedione Natural Product Hybrids of Parthenin Followed by Their Cytotoxicity Evaluation.小白菊内酯新型双螺-吡咯里西啶/硫代吡咯里西啶-氧化吲哚/茚二酮天然产物杂合物的半合成及其细胞毒性评价
ACS Omega. 2023 Sep 14;8(38):35283-35294. doi: 10.1021/acsomega.3c05020. eCollection 2023 Sep 26.
3
Azomethine ylide cycloaddition: a versatile tool for preparing novel pyrrolizidino-spiro-oxindolo hybrids of the doubly conjugated alkamide piperine.亚甲胺叶立德环加成：一种用于制备新型吡咯里西啶螺-氧吲哚稠合双共轭酰胺胡椒碱的多功能工具。
Mol Divers. 2020 Aug;24(3):627-639. doi: 10.1007/s11030-019-09969-w. Epub 2019 Jun 10.
4
Synthesis of Bis-pyrrolizidine-Fused Dispiro-oxindole Analogues of Curcumin via One-Pot Azomethine Ylide Cycloaddition: Experimental and Computational Approach toward Regio- and Diastereoselection.通过一锅法亚胺叶立德环加成合成姜黄素的双吡咯里西啶稠合双螺环氧化吲哚类似物：区域和非对映选择性的实验和计算方法。
Org Lett. 2015 Sep 18;17(18):4440-3. doi: 10.1021/acs.orglett.5b02085. Epub 2015 Sep 2.
5
Chemistry of withaferin-A: chemo, regio, and stereoselective synthesis of novel spiro-pyrrolizidino-oxindole adducts of withaferin-A via one-pot three-component [3+2] azomethine ylide cycloaddition and their cytotoxicity evaluation.睡茄内酯-A的化学性质：通过一锅三组分[3+2]甲亚胺叶立德环加成反应实现睡茄内酯-A新型螺-吡咯里西啶-氧化吲哚加合物的化学、区域和立体选择性合成及其细胞毒性评估。
Mol Divers. 2015 May;19(2):251-61. doi: 10.1007/s11030-015-9574-6. Epub 2015 Mar 8.
6
Regio- and stereoselective synthesis of a library of bioactive dispiro-oxindolo/acenaphthoquino andrographolides via 1,3-dipolar cycloaddition reaction under microwave irradiation.通过微波辐射下的 1,3-偶极环加成反应，区域和立体选择性合成具有生物活性的双螺-氧杂吲哚/吖萘并喹啉穿心莲内酯文库。
ACS Comb Sci. 2013 Jan 14;15(1):41-8. doi: 10.1021/co3001154. Epub 2012 Nov 29.
7
Synthesis of Functionalized 3-Spiro[cyclopropa[a]pyrrolizine]- and 3-Spiro[3-azabicyclo[3.1.0]hexane]oxindoles from Cyclopropenes and Azomethine Ylides via [3 + 2]-Cycloaddition.功能化 3-螺[环丙[a]吡咯嗪]-和 3-螺[3-氮杂双环[3.1.0]己烷]氧吲哚的环丙烷和亚胺叶立德通过[3 + 2]-环加成合成。
J Org Chem. 2017 Jan 20;82(2):959-975. doi: 10.1021/acs.joc.6b02505. Epub 2017 Jan 3.
8
Horner-Wadsworth-Emmons reagents as azomethine ylide analogues: pyrrole synthesis via (3 + 2) cycloaddition.作为吖丙啶类似物的霍纳-沃思瓦特-埃蒙斯试剂：通过（3 + 2）环加成合成吡咯。
Org Lett. 2010 Nov 5;12(21):4916-9. doi: 10.1021/ol102075y.
9
Isolation of phytochemicals from followed by semisynthetic modification of ixoside via azomethine ylide cycloaddition; computational approach towards chemo-selection.从 中分离植物化学物质，然后通过亚甲胺叶立德环加成对半合成修饰 ixoside；化学选择的计算方法。
Nat Prod Res. 2023 Jul;37(13):2215-2224. doi: 10.1080/14786419.2022.2037084. Epub 2022 Feb 6.
10
[3 + 2] Cycloaddition of Nonstabilized Azomethine Ylides. 7. Stereoselective Synthesis of Epibatidine and Analogues(,).[3 + 2] 非稳定偶氮甲碱叶立德的环加成反应。7. 表柔比星及其类似物的立体选择性合成(,)。
J Org Chem. 1998 Feb 6;63(3):760-768. doi: 10.1021/jo971728+.

引用本文的文献

1
Novel Functionalized Spiro [Indoline-3,5'-pyrroline]-2,2'dione Derivatives: Synthesis, Characterization, Drug-Likeness, ADME, and Anticancer Potential.新型功能化螺[吲哚啉-3,5'-吡咯啉]-2,2'-二酮衍生物：合成、表征、类药性、ADME 及抗癌潜力。
Int J Mol Sci. 2023 Apr 15;24(8):7336. doi: 10.3390/ijms24087336.
2
A review on biological activities of Schiff base, hydrazone, and oxime derivatives of curcumin.姜黄素席夫碱、腙和肟衍生物的生物活性综述。
RSC Adv. 2020 Aug 17;10(50):30186-30202. doi: 10.1039/d0ra05720g. eCollection 2020 Aug 10.

本文引用的文献

1
Sequential Multicomponent Strategy for the Diastereoselective Synthesis of Densely Functionalized Spirooxindole-Fused Thiazolidines.连续多组分策略用于非对映选择性合成稠合螺环氧化吲哚-噻唑烷。
ACS Comb Sci. 2018 Feb 12;20(2):98-105. doi: 10.1021/acscombsci.7b00179. Epub 2018 Jan 25.
2
Synthesis of Bis-pyrrolizidine-Fused Dispiro-oxindole Analogues of Curcumin via One-Pot Azomethine Ylide Cycloaddition: Experimental and Computational Approach toward Regio- and Diastereoselection.通过一锅法亚胺叶立德环加成合成姜黄素的双吡咯里西啶稠合双螺环氧化吲哚类似物：区域和非对映选择性的实验和计算方法。
Org Lett. 2015 Sep 18;17(18):4440-3. doi: 10.1021/acs.orglett.5b02085. Epub 2015 Sep 2.
3
Chemistry of withaferin-A: chemo, regio, and stereoselective synthesis of novel spiro-pyrrolizidino-oxindole adducts of withaferin-A via one-pot three-component [3+2] azomethine ylide cycloaddition and their cytotoxicity evaluation.
睡茄内酯-A的化学性质：通过一锅三组分[3+2]甲亚胺叶立德环加成反应实现睡茄内酯-A新型螺-吡咯里西啶-氧化吲哚加合物的化学、区域和立体选择性合成及其细胞毒性评估。
Mol Divers. 2015 May;19(2):251-61. doi: 10.1007/s11030-015-9574-6. Epub 2015 Mar 8.
4
One-pot sequential alkynylation and cycloaddition: regioselective construction and biological evaluation of novel benzoxazole-triazole derivatives.一锅法连续炔基化和环加成反应：新型苯并恶唑-三唑衍生物的区域选择性构建及生物学评价
ACS Comb Sci. 2015 Jan 12;17(1):39-48. doi: 10.1021/co500135z. Epub 2014 Dec 2.
5
Ultrasound-assisted sequential multicomponent strategy for the combinatorial synthesis of novel coumarin hybrids.用于新型香豆素杂化物组合合成的超声辅助顺序多组分策略
ACS Comb Sci. 2014 Oct 13;16(10):566-72. doi: 10.1021/co500092b. Epub 2014 Aug 27.
6
Biased and unbiased strategies to identify biologically active small molecules.用于识别生物活性小分子的偏向性和无偏向性策略。
Bioorg Med Chem. 2014 Aug 15;22(16):4474-89. doi: 10.1016/j.bmc.2014.04.019. Epub 2014 Apr 21.
7
Synthesis, characterization, and antioxidant and bleomycin-dependent DNA damage evaluation of curcumin analogs.姜黄素类似物的合成、表征及抗氧化和博来霉素依赖性 DNA 损伤评价。
Arch Pharm (Weinheim). 2014 Feb;347(2):123-33. doi: 10.1002/ardp.201300203. Epub 2013 Dec 2.
8
Sequential [3 + 2] and [4 + 2] cycloadditions for stereoselective synthesis of a novel polyheterocyclic scaffold.连续[3+2]和[4+2]环加成反应用于立体选择性合成新型多杂环支架。
ACS Comb Sci. 2013 Jul 8;15(7):350-5. doi: 10.1021/co400026s. Epub 2013 Jun 3.
9
Cytotoxic activity and apoptosis-inducing potential of di-spiropyrrolidino and di-spiropyrrolizidino oxindole andrographolide derivatives.二螺吡咯烷和二螺吡咯里嗪吲哚阿朴啡内酯衍生物的细胞毒性活性和诱导细胞凋亡的潜力。
PLoS One. 2013;8(3):e58055. doi: 10.1371/journal.pone.0058055. Epub 2013 Mar 5.
10
Regio- and stereoselective synthesis of a library of bioactive dispiro-oxindolo/acenaphthoquino andrographolides via 1,3-dipolar cycloaddition reaction under microwave irradiation.通过微波辐射下的 1,3-偶极环加成反应，区域和立体选择性合成具有生物活性的双螺-氧杂吲哚/吖萘并喹啉穿心莲内酯文库。
ACS Comb Sci. 2013 Jan 14;15(1):41-8. doi: 10.1021/co3001154. Epub 2012 Nov 29.