Studies toward the synthesis of azadirachtin, part 2 : construction of fully functionalized ABCD ring frameworks and unusual intramolecular reactions induced by close-proximity effects

Article

Nicolaou, K., Sasmal, P., Koftis, T., Converso, A., Loizidou, E., Kaiser, F., Roecker, A., Dellios, C., Sun, X. and Petrovic, G. 2005. Studies toward the synthesis of azadirachtin, part 2 : construction of fully functionalized ABCD ring frameworks and unusual intramolecular reactions induced by close-proximity effects. Angewandte Chemie International Edition. 44 (22), pp. 3447-3452. https://doi.org/10.1002/anie.200500217
TypeArticle
TitleStudies toward the synthesis of azadirachtin, part 2 : construction of fully functionalized ABCD ring frameworks and unusual intramolecular reactions induced by close-proximity effects
AuthorsNicolaou, K., Sasmal, P., Koftis, T., Converso, A., Loizidou, E., Kaiser, F., Roecker, A., Dellios, C., Sun, X. and Petrovic, G.
Abstract

The remarkable antifeedant agent and insecticide, azadirachtin (1), has, to date, escaped a total synthesis. The preparation of an advanced precursor has revealed some of the inner intricacies of this uniquely crowded and highly functionalized molecular architecture.

PublisherWiley
Gesellschaft Deutscher Chemiker
JournalAngewandte Chemie International Edition
ISSN1433-7851
Electronic1521-3773
Publication dates
Online22 Apr 2005
Print30 May 2005
Publication process dates
Submitted19 Jan 2005
Deposited06 Mar 2015
Output statusPublished
Digital Object Identifier (DOI)https://doi.org/10.1002/anie.200500217
LanguageEnglish
Permalink -

https://repository.mdx.ac.uk/item/84z32

Log in to edit
  • 21
    total views
  • 0
    total downloads
  • 1
    views this month
  • 0
    downloads this month

Export as

Related outputs

Identification of a new class of proteasome inhibitors based on a naphthyl-azotricyclic-urea-phenyl scaffold
Allardyce, D., Adu Mantey, P., Szalecka, M., Nkwo, R. and Loizidou, E. 2023. Identification of a new class of proteasome inhibitors based on a naphthyl-azotricyclic-urea-phenyl scaffold. RSC Medicinal Chemistry. 14 (3), pp. 573-582. https://doi.org/10.1039/D2MD00404F
An experimental FTIR-ATR and computational study of H-bonding in ethanol/water mixtures
Zeinalipour-Yazdi, C. and Loizidou, E. 2021. An experimental FTIR-ATR and computational study of H-bonding in ethanol/water mixtures. Chemical Physics. 550 (1), pp. 1-7. https://doi.org/10.1016/j.chemphys.2021.111295
Nanoparticle-infused-biodegradable-microneedles as drug-delivery systems: Preparation and characterisation
Sully, R., Garelick, H., Loizidou, E., Podoleanu, A. and Gubala, V. 2021. Nanoparticle-infused-biodegradable-microneedles as drug-delivery systems: Preparation and characterisation. Materials Advances. 2 (16), pp. 5432-5442. https://doi.org/10.1039/D1MA00135C
Nanomedicines and microneedles: A guide to their analysis and application
Sully, R., Moore, C., Garelick, H., Loizidou, E., Podoleanu, A. and Gubala, V. 2021. Nanomedicines and microneedles: A guide to their analysis and application. Analytical Methods. 13 (30), pp. 3326-3347. https://doi.org/10.1039/d1ay00954k
Size-dependent bond dissociation enthalpies in single-walled carbon nanotubes
Zenalipour-Yazdi, C., Loizidou, E. and Chutia, A. 2019. Size-dependent bond dissociation enthalpies in single-walled carbon nanotubes. Chemical Physics Letters. 731, pp. 1-6. https://doi.org/10.1016/j.cplett.2019.136628
Argyrin B a non-competitive inhibitor of the human immunoproteasome exhibiting preference for β1i
Allardyce, D., Bell, C. and Loizidou, E. 2019. Argyrin B a non-competitive inhibitor of the human immunoproteasome exhibiting preference for β1i. Chemical Biology and Drug Design. 94 (2), pp. 1556-1567. https://doi.org/10.1111/cbdd.13539
The potential use of microneedles as an alternative method for skin cancer treatment
Loizidou, E., Yagnik, D., Szalecka, M. and Nguyen, D. 2019. The potential use of microneedles as an alternative method for skin cancer treatment. The World Congress on Advanced Treatments and Technologies in Skin Cancer (Skin-Cancer2019). Vienna, Austria 04 - 05 Apr 2019
Analysis of argyrin B binding at constitutive and immunoproteasome active sites using molecular modelling and kinetic assays
Allardyce, D., Bell, C. and Loizidou, E. 2017. Analysis of argyrin B binding at constitutive and immunoproteasome active sites using molecular modelling and kinetic assays. Computational Advances in Drug Discovery (Structure Based Drug Design). Lausanne, Switzerland 05 - 08 Sep 2017
Teaching atomic structure as a threshold concept in chemistry for biologists
Loizidou, E. and Jones, H. 2016. Teaching atomic structure as a threshold concept in chemistry for biologists. 253rd American Chemical Society National Meeting & Exposition. San Francisco, CA, USA 02 - 06 Apr 2017
Study of the cap structure of (3,3), (4,4) and (5,5)-SWCNTs: application of the sphere-in-contact model
Zeinalipour-Yazdi, C. and Loizidou, E. 2017. Study of the cap structure of (3,3), (4,4) and (5,5)-SWCNTs: application of the sphere-in-contact model. Carbon. 115, pp. 819-827. https://doi.org/10.1016/j.carbon.2017.01.074
Evaluation of geometrical effects of microneedles on skin penetration by CT scan and finite element analysis
Loizidou, E., Inoue, N., Ashton-Barnett, J., Barrow, D. and Allender, C. 2016. Evaluation of geometrical effects of microneedles on skin penetration by CT scan and finite element analysis. European Journal of Pharmaceutics and Biopharmaceutics. 107, pp. 1-6. https://doi.org/10.1016/j.ejpb.2016.06.023
AB diblock and ABC triblock amphiphilic copolymers containing fluorine
Loizidou, E., Haralambous, D., Vamvakaki, M., Patrickios, C., Krasia, T. and Antonietti, M. 2001. AB diblock and ABC triblock amphiphilic copolymers containing fluorine. 221th ACS National Meeting. San Diego, CA, USA 01 Apr 2001
Characterization of amphiphilic polymers covalently attached with Pirkle-concept chiral selectors for chiral seperations by Merck
Loizidou, E., Zhang, K. and Sun, L. 2002. Characterization of amphiphilic polymers covalently attached with Pirkle-concept chiral selectors for chiral seperations by Merck. 224th ACS National Meeting. 18 Aug 2002
Molecular recognition of barbiturate artificial receptor covalently bound to an amphiphilic copolymer
Loizidou, E. and Sun, L. 2003. Molecular recognition of barbiturate artificial receptor covalently bound to an amphiphilic copolymer. International Symposium on the Synthesis and Characterization of Macromolecules. Amsterdam, Netherlands 07 - 11 Feb 2003
Structure-based computational analysis of the implications of subtype specific polymorphisms on the efficacy of integrase inhibitors
Loizidou, E., Kousiappa, I., Zeinalipour-Yazdi, C., Van De Vijver, D. and Kostrikis, L. 2009. Structure-based computational analysis of the implications of subtype specific polymorphisms on the efficacy of integrase inhibitors. 7th European HIV Drug Resistance Workshop. Stockholm, Sweden
Rational design of argyrin analogues as selective inhibitors of the proteasome
Loizidou, E. and Zeinalipour-Yazdi, C. 2012. Rational design of argyrin analogues as selective inhibitors of the proteasome. COST Conference on Personalised Medicine. Larnaca, Cyprus 17 - 22 Jun 2012
Design of argyrin analogues as proteasome inhibitors with subunit specicificity
Loizidou, E. and Zeinalipour-Yazdi, C. 2014. Design of argyrin analogues as proteasome inhibitors with subunit specicificity. 247th ACS National Meeting. Dallas, TX, USA 16 - 20 Mar 2014
Simulating the effect of geometry on the structural properties of microneedles
Loizidou, E., Ashton-Barnett, J., Barrow, D. and Allender, C. 2014. Simulating the effect of geometry on the structural properties of microneedles. Perspectives in Percutaneous Penetration Fourteenth International Conference including FP7 HIPODERM Symposium on High Potency Dermatologicals. La Grande Motte, France 23 - 25 Apr 2014
Structural properties of sugar microneedles: a finite element analysis
Loizidou, E., Barrow, D. and Allender, C. 2014. Structural properties of sugar microneedles: a finite element analysis. Perspectives in Percutaneous Penetration Fourteenth International Conference including FP7 HIPODERM Symposium on High Potency Dermatologicals. La Grande Motte, France 23 - 25 Apr 2014
Implications of HIV-1 M group polymorphisms on intergase inhibitor efficacy and resistance: genetic and structural in-silico analyses
Loizidou, E., Kousiappa, I., Zeinalipour-Yazdi, C., Van De Vijver, D. and Kostrikis, L. 2009. Implications of HIV-1 M group polymorphisms on intergase inhibitor efficacy and resistance: genetic and structural in-silico analyses. Biochemistry. 48 (1), pp. 4-6. https://doi.org/10.1021/bi8019349
Molecular recognition of barbiturate artificial receptor covalently bound to an amphiphilic copolymer
Loizidou, E. and Sun, L. 2003. Molecular recognition of barbiturate artificial receptor covalently bound to an amphiphilic copolymer. 226th ACS National Meeting. New York, New York, USA 07 - 11 Sep 2003
Part I: total synthesis of azaspiracid-3 Part II: molecular recognition studies in aqueous solutions facilitated by a receptor-modified polymer
Loizidou, E. 2006. Part I: total synthesis of azaspiracid-3 Part II: molecular recognition studies in aqueous solutions facilitated by a receptor-modified polymer. PhD thesis University of California San Diego / San Diego State University Chemistry
HIV-1 integrase inhibitors: from biology to chemotherapeutics
Loizidou, E., Nicolaou, C., Nicolaides, A. and Kostrikis, L. 2007. HIV-1 integrase inhibitors: from biology to chemotherapeutics. Current HIV Research. 5 (4), pp. 365-388. https://doi.org/10.2174/157016207781023965
Multi-objective optimization methods in de novo drug design
Nicolaou, C., Kannas, C. and Loizidou, E. 2012. Multi-objective optimization methods in de novo drug design. Mini Reviews in Medicinal Chemistry. 12 (10), pp. 979-987. https://doi.org/10.2174/138955712802762284
Structural assignment and total synthesis of azaspiracid-1
Frederick, M., Cole, K., Petrovic, G., Loizidou, E. and Nicolaou, K. 2007. Structural assignment and total synthesis of azaspiracid-1. in: Botana, L. (ed.) Phycotoxins: chemistry and biochemistry Ames, Iowa WileyBlackwell. pp. 297-309
Computational inhibition studies of the human proteasome by argyrin-based analogues with subunit specificity
Loizidou, E. and Zeinalipour-Yazdi, C. 2014. Computational inhibition studies of the human proteasome by argyrin-based analogues with subunit specificity. Chemical Biology and Drug Design. 84 (1), pp. 99-107. https://doi.org/10.1111/cbdd.12298
Receptor-attached amphiphilic terpolymer for selective drug recognition in aqueous solutions
Loizidou, E., Sun, L. and Zeinalipour-Yazdi, C. 2011. Receptor-attached amphiphilic terpolymer for selective drug recognition in aqueous solutions. Journal of Molecular Recognition. 24 (4), pp. 678-686. https://doi.org/10.1002/jmr.1098
Analysis of binding parameters of HIV-1 integrase inhibitors: correlates of drug inhibition and resistance
Loizidou, E., Zeinalipour-Yazdi, C., Christofides, T. and Kostrikis, L. 2009. Analysis of binding parameters of HIV-1 integrase inhibitors: correlates of drug inhibition and resistance. Bioorganic & Medicinal Chemistry. 17 (13), pp. 4806-4818. https://doi.org/10.1016/j.bmc.2009.04.058
Second generation total synthesis of azaspiracids-1, -2 and -3
Nicolaou, K., Frederick, M., Loizidou, E., Petrovic, G., Cole, K., Koftis, T. and Yamada, Y. 2006. Second generation total synthesis of azaspiracids-1, -2 and -3. Chemistry: an Asian Journal. 1 (1-2), pp. 245-263. https://doi.org/10.1002/asia.200600059
Structural characterization and transdermal delivery studies on sugar microneedles: experimental and finite element modelling analyses
Loizidou, E., Williams, N., Barrow, D., Eaton, M., McCrory, J., Evans, S. and Allender, C. 2015. Structural characterization and transdermal delivery studies on sugar microneedles: experimental and finite element modelling analyses. European Journal of Pharmaceutics and Biopharmaceutics. 89, pp. 224-231. https://doi.org/10.1016/j.ejpb.2014.11.023
Total synthesis and confirmation of the revised structures of azaspiracid-2 and azaspiracid-3
Nicolaou, K., Frederick, M., Petrovic, G., Cole, K. and Loizidou, E. 2006. Total synthesis and confirmation of the revised structures of azaspiracid-2 and azaspiracid-3. Angewandte Chemie International Edition. 45 (16), pp. 2609-2615. https://doi.org/10.1002/anie.200600295
Total synthesis and structural elucidation of azaspiracid-1 : construction of key building blocks for originally proposed structure
Nicolaou, K., Pihko, P., Bernal, F., Frederick, M., Qian, W., Uesaka, N., Diedrichs, N., Hinrichs, J., Koftis, T., Loizidou, E., Petrovic, G., Rodriquez, M., Sarlah, D. and Zou, N. 2006. Total synthesis and structural elucidation of azaspiracid-1 : construction of key building blocks for originally proposed structure. Journal of the American Chemical Society. 128 (7), pp. 2244-2257. https://doi.org/10.1021/ja0547477
Artificial receptor-attached amphiphilic copolymer for barbiturate binding in aqueous media
Loizidou, E., Zeinalipour-Yazdi, C. and Sun, L. 2004. Artificial receptor-attached amphiphilic copolymer for barbiturate binding in aqueous media. Biomacromolecules. 5 (5), pp. 1647-1652. https://doi.org/10.1021/bm0497320
Synthesis and characterization of novel networks with nano-engineered structures: cross-linked star homopolymers
Vamvakaki, M., Hadjiyiannakou, S., Loizidou, E. and Patrickios, C. 2001. Synthesis and characterization of novel networks with nano-engineered structures: cross-linked star homopolymers. Chemistry of Materials. 13 (12), pp. 4738-4744. https://doi.org/10.1021/cm010569e