With Unprotected Amino Acids to Tetrazolo Peptidomimetics

Overview

Journal Chem Commun (Camb)

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2017 Jul 15

PMID 28707691

Citations 4

Authors

Rudrakshula Madhavachary

Qian Wang

Alexander Domling

Affiliations

Soon will be listed here.

Abstract

Here we describe the direct usage of C,N-unprotected amino acids in Ugi-tetrazole reactions to produce a novel class of acid-tetrazole compounds. Surprisingly, only the tetrazole Ugi product is found and not traces of other possible Ugi type reactions. Based on this reaction pathway we have designed the synthesis of novel tetrazole-peptidomimetics. A high level of structural diversity can be achieved using this isocyanide based multicomponent reaction (IMCR), providing a platform for the production of functionalized building blocks for novel bioactive molecules and nontraditional scaffolds which previously were not accessible.

Citing Articles

Appendage- and Scaffold-Diverse Electrophilic and Photoreactive Probes for Integrated Phenotypic Screening-Target Identification Campaigns via a Minimalist Bifunctional Isocyanide.

Jackson P, Kisty E, Pradhan V, Swank C, Bohrer L, Nolan T ACS Omega. 2024; 9(41):42557-42570.

PMID: 39431108 PMC: 11483914. DOI: 10.1021/acsomega.4c06879.

Design, synthesis and biological evaluation of 1,5-disubstituted α-amino tetrazole derivatives as non-covalent inflammasome-caspase-1 complex inhibitors with potential application against immune and inflammatory disorders.

Ulgheri F, Spanu P, Deligia F, Loriga G, Fuggetta M, de Haan I Eur J Med Chem. 2021; 229:114002.

PMID: 34823899 PMC: 8598261. DOI: 10.1016/j.ejmech.2021.114002.

Isoquinolone-4-Carboxylic Acids by Ammonia-Ugi-4CR and Copper-Catalyzed Domino Reaction.

Wang Q, Mgimpatsang K, Li X, Domling A J Org Chem. 2021; 86(14):9771-9780.

PMID: 34184894 PMC: 8291606. DOI: 10.1021/acs.joc.1c01170.

Synthesis of (macro)heterocycles by consecutive/repetitive isocyanide-based multicomponent reactions.

Barreto A, Kleber Z Andrade C Beilstein J Org Chem. 2019; 15:906-930.

PMID: 31164928 PMC: 6541343. DOI: 10.3762/bjoc.15.88.

References

Zhang J, Jacobson A, Rusche J, Herlihy W . Unique Structures Generated by Ugi 3CC Reactions Using Bifunctional Starting Materials Containing Aldehyde and Carboxylic Acid. J Org Chem. 2001; 64(3):1074-1076. DOI: 10.1021/jo982192a. View

Abdelraheem E, Kurpiewska K, Kalinowska-Tluscik J, Domling A . Artificial Macrocycles by Ugi Reaction and Passerini Ring Closure. J Org Chem. 2016; 81(19):8789-8795. PMC: 6280654. DOI: 10.1021/acs.joc.6b01430. View

Khoury K, Sinha M, Nagashima T, Herdtweck E, Domling A . Efficient assembly of iminodicarboxamides by a "truly" four-component reaction. Angew Chem Int Ed Engl. 2012; 51(41):10280-3. PMC: 3874142. DOI: 10.1002/anie.201205366. View

Ugi I, Ebert B, Horl W . Formation of 1,1'-iminodicarboxylic acid derivatives, 2,6-diketo-piperazine and dibenzodiazocine-2,6-dione by variations of multicomponent reactions. Chemosphere. 2001; 43(1):75-81. DOI: 10.1016/s0045-6535(00)00326-x. View

Gargano A, Buchinger S, Kohout M, Lindner W, Lammerhofer M . Single-step Ugi multicomponent reaction for the synthesis of phosphopeptidomimetics. J Org Chem. 2013; 78(20):10077-87. DOI: 10.1021/jo401372x. View

Hulme C, Gore V . "Multi-component reactions : emerging chemistry in drug discovery" 'from xylocain to crixivan'. Curr Med Chem. 2003; 10(1):51-80. DOI: 10.2174/0929867033368600. View

Elders N, van der Born D, Hendrickx L, Timmer B, Krause A, Janssen E . The efficient one-pot reaction of up to eight components by the union of multicomponent reactions. Angew Chem Int Ed Engl. 2009; 48(32):5856-9. DOI: 10.1002/anie.200902683. View

Patil P, Madhavachary R, Kurpiewska K, Kalinowska-Tluscik J, Domling A . De Novo Assembly of Highly Substituted Morpholines and Piperazines. Org Lett. 2017; 19(3):642-645. PMC: 5348101. DOI: 10.1021/acs.orglett.6b03807. View

Sinha M, Khoury K, Herdtweck E, Domling A . Various cyclization scaffolds by a truly Ugi 4-CR. Org Biomol Chem. 2013; 11(29):4792-6. PMC: 3772509. DOI: 10.1039/c3ob40523k. View

10.

Zhao T, Boltjes A, Herdtweck E, Domling A . Tritylamine as an ammonia surrogate in the Ugi tetrazole synthesis. Org Lett. 2013; 15(3):639-41. DOI: 10.1021/ol303348m. View

11.

Kambe T, Correia B, Niphakis M, Cravatt B . Mapping the protein interaction landscape for fully functionalized small-molecule probes in human cells. J Am Chem Soc. 2014; 136(30):10777-82. PMC: 4120992. DOI: 10.1021/ja505517t. View

12.

Herr R . 5-Substituted-1H-tetrazoles as carboxylic acid isosteres: medicinal chemistry and synthetic methods. Bioorg Med Chem. 2002; 10(11):3379-93. DOI: 10.1016/s0968-0896(02)00239-0. View

13.

Zarganes-Tzitzikas T, Chandgude A, Domling A . Multicomponent Reactions, Union of MCRs and Beyond. Chem Rec. 2015; 15(5):981-96. DOI: 10.1002/tcr.201500201. View

14.

Domling A, Wang W, Wang K . Chemistry and biology of multicomponent reactions. Chem Rev. 2012; 112(6):3083-135. PMC: 3712876. DOI: 10.1021/cr100233r. View

15.

Cheron N, Ramozzi R, Kaim L, Grimaud L, Fleurat-Lessard P . Challenging 50 years of established views on Ugi reaction: a theoretical approach. J Org Chem. 2012; 77(3):1361-6. DOI: 10.1021/jo2021554. View

16.

Koopmanschap G, Ruijter E, Orru R . Isocyanide-based multicomponent reactions towards cyclic constrained peptidomimetics. Beilstein J Org Chem. 2014; 10:544-98. PMC: 3943360. DOI: 10.3762/bjoc.10.50. View

17.

Plant A, Thompson P, Williams D . Application of the Ugi reaction for the one-pot synthesis of uracil polyoxin C analogues. J Org Chem. 2009; 74(13):4870-3. DOI: 10.1021/jo900244m. View

18.

Neochoritis C, Stotani S, Mishra B, Domling A . Efficient isocyanide-less isocyanide-based multicomponent reactions. Org Lett. 2015; 17(8):2002-5. PMC: 4733495. DOI: 10.1021/acs.orglett.5b00759. View

19.

Ruijter E, Scheffelaar R, Orru R . Multicomponent reaction design in the quest for molecular complexity and diversity. Angew Chem Int Ed Engl. 2011; 50(28):6234-46. DOI: 10.1002/anie.201006515. View

20.

Gedey S, Van der Eycken J, Fulop F . Liquid-phase combinatorial synthesis of alicyclic beta-lactams via Ugi four-component reaction. Org Lett. 2002; 4(11):1967-9. DOI: 10.1021/ol025986r. View