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Literature DB >> 31592212

Synthesis of a C₁-C₂₃ fragment of the archazolids and evidence for V-ATPase but not COX inhibitory activity.

Gregory W O'Neil¹, Alexander M Craig¹, John R Williams¹, Jeffrey C Young², P Clint Spiegel¹.

Abstract

A convergent synthesis of a C1-C23 fragment of the archazolids has been completed based on a high yielding Stille coupling to costruct the substituted Z,Z,E-conjugated triene. After removal of the protecting groups, the resulting tetrol exhibited evidence for inhibition of the vacuolar-type ATPase (V-ATPase) but not cyclooxygenase (COX) inhibitory activity.

Entities: Chemical Disease Gene Species

Keywords: Stille reaction; V-ATPase; archazolid; cyclooxygenase; natural product; total synthesis

Year: 2017 PMID： 31592212 PMCID： PMC6779165 DOI： 10.1055/s-0036-1588413

Source DB: PubMed Journal: Synlett ISSN： 0936-5214 Impact factor: 2.454

27 in total

1. Ligand configurational entropy and protein binding.

Authors: Chia-en A Chang; Wei Chen; Michael K Gilson
Journal: Proc Natl Acad Sci U S A Date: 2007-01-22 Impact factor: 11.205

2. Revealing the macromolecular targets of complex natural products.

Authors: Daniel Reker; Anna M Perna; Tiago Rodrigues; Petra Schneider; Michael Reutlinger; Bettina Mönch; Andreas Koeberle; Christina Lamers; Matthias Gabler; Heinrich Steinmetz; Rolf Müller; Manfred Schubert-Zsilavecz; Oliver Werz; Gisbert Schneider
Journal: Nat Chem Date: 2014-11-02 Impact factor: 24.427

3. Vacuolar-ATPase Inhibition Blocks Iron Metabolism to Mediate Therapeutic Effects in Breast Cancer.

Authors: Lina S Schneider; Karin von Schwarzenberg; Thorsten Lehr; Melanie Ulrich; Rebekka Kubisch-Dohmen; Johanna Liebl; Dirk Trauner; Dirk Menche; Angelika M Vollmar
Journal: Cancer Res Date: 2015-05-27 Impact factor: 12.701

4. Highly stereo- and regioselective synthesis of (Z)-trisubstituted alkenes via 1-bromo-1-alkyne hydroboration-migratory insertion-Zn-promoted iodinolysis and Pd-catalyzed organozinc cross-coupling.

Authors: Zhihong Huang; Ei-ichi Negishi
Journal: J Am Chem Soc Date: 2007-11-07 Impact factor: 15.419

5. A versatile protocol for Stille-Migita cross coupling reactions.

Authors: Alois Fürstner; Jacques-Alexis Funel; Martin Tremblay; Laure C Bouchez; Cristina Nevado; Mario Waser; Jens Ackerstaff; Christopher C Stimson
Journal: Chem Commun (Camb) Date: 2008-06-02 Impact factor: 6.222

6. Exploring a Ring-Closing Metathesis Approach to the Archazolid Macrocycle.

Authors: Brianne R King; Steven M Swick; Sara L Schaefer; Jamie R Welch; Emily F Hunter; Gregory W O'Neil
Journal: Synthesis (Stuttg) Date: 2014-08-15 Impact factor: 3.157

7. Modular total synthesis of archazolid A and B.

Authors: Dirk Menche; Jorma Hassfeld; Jun Li; Kerstin Mayer; Sven Rudolph
Journal: J Org Chem Date: 2009-10-02 Impact factor: 4.354

8. Targeting V-ATPase in primary human monocytes by archazolid potently represses the classical secretion of cytokines due to accumulation at the endoplasmic reticulum.

Authors: Olga Scherer; Heinrich Steinmetz; Christoph Kaether; Christina Weinigel; Dagmar Barz; Hartmut Kleinert; Dirk Menche; Rolf Müller; Carlo Pergola; Oliver Werz
Journal: Biochem Pharmacol Date: 2014-08-12 Impact factor: 5.858

9. The first hydroxylated archazolid from the myxobacterium Cystobacter violaceus: isolation, structural elucidation and V-ATPase inhibition.

Authors: Dirk Menche; Jorma Hassfeld; Heinrich Steinmetz; Markus Huss; Helmut Wieczorek; Florenz Sasse
Journal: J Antibiot (Tokyo) Date: 2007-05 Impact factor: 2.649

Synthesis of a C₁-C₂₃ fragment of the archazolids and evidence for V-ATPase but not COX inhibitory activity.

1. Ligand configurational entropy and protein binding.

2. Revealing the macromolecular targets of complex natural products.

3. Vacuolar-ATPase Inhibition Blocks Iron Metabolism to Mediate Therapeutic Effects in Breast Cancer.

4. Highly stereo- and regioselective synthesis of (Z)-trisubstituted alkenes via 1-bromo-1-alkyne hydroboration-migratory insertion-Zn-promoted iodinolysis and Pd-catalyzed organozinc cross-coupling.

5. A versatile protocol for Stille-Migita cross coupling reactions.

6. Exploring a Ring-Closing Metathesis Approach to the Archazolid Macrocycle.

7. Modular total synthesis of archazolid A and B.

8. Targeting V-ATPase in primary human monocytes by archazolid potently represses the classical secretion of cytokines due to accumulation at the endoplasmic reticulum.

9. The first hydroxylated archazolid from the myxobacterium Cystobacter violaceus: isolation, structural elucidation and V-ATPase inhibition.

10. Concanamycin A, the specific inhibitor of V-ATPases, binds to the V(o) subunit c.

1. Design, Synthesis and Biological Evaluation of Highly Potent Simplified Archazolids.

2. Suzuki coupling-based synthesis of VATPase inhibitor archazolid natural product derived fragments.

Review 3. Recent advances in transition metal-free catalytic hydroelementation (E = B, Si, Ge, and Sn) of alkynes.

Review 4. Design and Synthesis of Simplified Polyketide Analogs: New Modalities beyond the Rule of 5.