Macrocyclic Drugs and Synthetic Methodologies toward Macrocycles

A review of telavancin in the treatment of complicated skin and skin structure infections (cSSSI)

(2016) Lala Dunbar   Therapeutics and Clinical Risk Management

Alkyne Metathesis on the Rise

(2013) Alois Fürstner   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Efficient and Selective Formation of Macrocyclic Disubstituted Z Alkenes by Ring-Closing Metathesis (RCM) Reactions Catalyzed by Mo- or W-Based Monoaryloxide Pyrrolide (MAP) Complexes: Applications to Total Syntheses of Epilachnene, Yuzu Lactone, Ambretto

(2013) Chenbo Wang et al.   CHEMISTRY-A EUROPEAN JOURNAL

Formal Total Synthesis of the Algal Toxin (−)-Polycavernoside A

(2013) Lennart Brewitz et al.   CHEMISTRY-A EUROPEAN JOURNAL

Syntheses and evaluation of macrocyclic engelhardione analogs as antitubercular and antibacterial agents

(2013) Li Shen et al.   JOURNAL OF ANTIBIOTICS

Total synthesis of the big four antibiotics and related antibiotics

(2013) Kuniaki Tatsuta   JOURNAL OF ANTIBIOTICS

A Highly Convergent and Efficient Synthesis of a Macrocyclic Hepatitis C Virus Protease Inhibitor BI 201302

(2013) Xudong Wei et al.   ORGANIC LETTERS

Efficient Construction of Proline-Containing β-Turn Mimetic Cyclic Tetrapeptides via CuAAC Macrocyclization

(2013) Gagan Chouhan et al.   ORGANIC LETTERS

Intramolecular Base-Free Sonogashira Reaction for the Synthesis of Benzannulated Chiral Macrocycles Embedded in Carbohydrate Templates

(2012) Altaf Hussain et al.   ADVANCED SYNTHESIS & CATALYSIS

Total Synthesis of Rhizopodin

(2012) Michael Dieckmann et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Fidaxomicin for the Treatment of Clostridium difficile Infections

(2012) C. B. Whitman et al.   ANNALS OF PHARMACOTHERAPY

The biology and chemistry of antifungal agents: A review

(2012) Muthu K Kathiravan et al.   BIOORGANIC & MEDICINAL CHEMISTRY

Microwave accelerated Glaser–Hay macrocyclizations at high concentrations

(2012) Anne-Catherine Bédard et al.   CHEMICAL COMMUNICATIONS

Peptidic macrocyclization via palladium-catalyzed chemoselective indole C-2 arylation

(2012) Huijun Dong et al.   CHEMICAL COMMUNICATIONS

Update 1 of: Macrolactonizations in the Total Synthesis of Natural Products

(2012) A. Parenty et al.   CHEMICAL REVIEWS

Diversity-oriented synthesis: producing chemical tools for dissecting biology

(2012) Cornelius J. O' Connor et al.   CHEMICAL SOCIETY REVIEWS

The Chemistry and Biology of the Bryostatins: Potential PKC Inhibitors in Clinical Development

(2012) B.-F. Ruan et al.   CURRENT MEDICINAL CHEMISTRY

Recent Researches in Triazole Compounds as Medicinal Drugs

(2012) C. -H. Zhou et al.   CURRENT MEDICINAL CHEMISTRY

Ivermectin in Human Medicine, An Overview of the Current Status of Its Clinical Applications

(2012) P. Gonzalez et al.   CURRENT PHARMACEUTICAL BIOTECHNOLOGY

Macrocycles in new drug discovery

(2012) Jamie Mallinson et al.   Future Medicinal Chemistry

Stereoselective Total Synthesis of FD-891

(2012) J. S. Yadav et al.   JOURNAL OF ORGANIC CHEMISTRY

Concise Synthesis of the Macrocyclic Core of Rhizopodin by a Heck Macrocyclization Strategy

(2012) Michael Dieckmann et al.   JOURNAL OF ORGANIC CHEMISTRY

Stereoselective Access to Z and E Macrocycles by Ruthenium-Catalyzed Z-Selective Ring-Closing Metathesis and Ethenolysis

(2012) Vanessa M. Marx et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Triple Click Reaction Strategy for Macromolecular Diversity

(2012) Umit Tunca   MACROMOLECULAR RAPID COMMUNICATIONS

From natural product to marketed drug: the tiacumicin odyssey

(2012) William Erb et al.   NATURAL PRODUCT REPORTS

A diversity-oriented synthesis approach to macrocycles via oxidative ring expansion

(2012) Felix Kopp et al.   Nature Chemical Biology

A two-directional strategy for the diversity-oriented synthesis of macrocyclic scaffolds

(2012) Kieron M. G. O'Connell et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Stereoselective Synthesis of the Monomeric Unit of Actin Binding Macrolide Rhizopodin

(2012) Kiran Kumar Pulukuri et al.   ORGANIC LETTERS

Toward an Enantioselective Synthesis of (−)-Zampanolide: Preparation of the C9–C20 Region

(2012) Matthew R. Wilson et al.   ORGANIC LETTERS

Diversity Oriented Synthesis of Pyran Based Polyfunctional Stereogenic Macrocyles and Their Conformational Studies

(2012) Arya Ajay et al.   ORGANIC LETTERS

Direct Imine Acylation: Synthesis of the Proposed Structures of ‘Upenamide

(2012) William P. Unsworth et al.   ORGANIC LETTERS

Diversity-Oriented Approach to Macrocyclic Cyclophane Derivatives via Ring-Closing Metathesis

(2012) Sambasivarao Kotha et al.   SYNLETT

Microwave-assisted synthesis of macrocycles via intramolecular and/or bimolecular Ullmann coupling

(2012) Li Shen et al.   TETRAHEDRON LETTERS

An easy two step synthesis of macrocyclic peptidotriazoles via a four-component reaction and copper catalyzed intramolecular azide–alkyne [3+2] click cycloaddition

(2012) D. Bahulayan et al.   TETRAHEDRON LETTERS

Emac – a comparative index for the assessment of macrocyclization efficiency

(2012) James C. Collins et al.   MedChemComm

Build/Couple/Pair Strategy for the Synthesis of Stereochemically Diverse Macrolactams via Head-to-Tail Cyclization

(2012) Mark E. Fitzgerald et al.   ACS Combinatorial Science

Synthesis of self-assembling glycerotriazolophanes

(2012) Mohit Tyagi et al.   RSC Advances

Echinocandins: Addressing outstanding questions surrounding treatment of invasive fungal infections

(2011) S. L. Holt et al.   AMERICAN JOURNAL OF HEALTH-SYSTEM PHARMACY

“Triazole Bridge”: Disulfide-Bond Replacement by Ruthenium-Catalyzed Formation of 1,5-Disubstituted 1,2,3-Triazoles

(2011) Martin Empting et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Recent advances in the development of alkyne metathesis catalysts

(2011) Xian Wu et al.   Beilstein Journal of Organic Chemistry

Macrocyclic lactams as potent Hsp90 inhibitors with excellent tumor exposure and extended biomarker activity

(2011) Christoph W. Zapf et al.   BIOORGANIC & MEDICINAL CHEMISTRY LETTERS

Discovery of a macrocyclic o-aminobenzamide Hsp90 inhibitor with heterocyclic tether that shows extended biomarker activity and in vivo efficacy in a mouse xenograft model

(2011) Christoph W. Zapf et al.   BIOORGANIC & MEDICINAL CHEMISTRY LETTERS

Design and SAR of macrocyclic Hsp90 inhibitors with increased metabolic stability and potent cell-proliferation activity

(2011) Christoph W. Zapf et al.   BIOORGANIC & MEDICINAL CHEMISTRY LETTERS

Microwave-assisted synthesis of medium-sized heterocycles

(2011) Abhishek Sharma et al.   CHEMICAL COMMUNICATIONS

Macrocyclic Proteasome Inhibitors

(2011) D. Krahn et al.   CURRENT MEDICINAL CHEMISTRY

Significant Breakthroughs in Search for Anti-Infectious Agents Derived from Erythromycin A

(2011) Xiaodong Ma et al.   CURRENT MEDICINAL CHEMISTRY

Biologically Active Macrocyclic Compounds - from Natural Products to Diversity-Oriented Synthesis

(2011) Charlotte M. Madsen et al.   EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Potent Macrocyclic Inhibitors of Insulin-Regulated Aminopeptidase (IRAP) by Olefin Ring-Closing Metathesis

(2011) Hanna Andersson et al.   JOURNAL OF MEDICINAL CHEMISTRY

Macrocycles Are Great Cycles: Applications, Opportunities, and Challenges of Synthetic Macrocycles in Drug Discovery

(2011) Eric Marsault et al.   JOURNAL OF MEDICINAL CHEMISTRY

Selective Binding ofD2h-Symmetrical, Acetylene-Linked Pyridine/Pyridone Macrocycles to Maltoside

(2011) Hajime Abe et al.   JOURNAL OF ORGANIC CHEMISTRY

Diversity-Oriented Synthesis of 13- to 18-Membered Macrolactams via Ring-Closing Metathesis

(2011) Sivaraman Dandapani et al.   JOURNAL OF ORGANIC CHEMISTRY

Synthesis of Vaniprevir (MK-7009): Lactamization To Prepare a 22-Membered Macrocycle

(2011) Zhiguo J. Song et al.   JOURNAL OF ORGANIC CHEMISTRY

Preparation of Shape-Persistent Macrocycles with a Single Pyridine Unit by Double Cross-Coupling Reactions of Aryl Bromides and Alkynes

(2011) Ryu Yamasaki et al.   JOURNAL OF ORGANIC CHEMISTRY

Total Synthesis of (−)-4,8,10-Tridesmethyl Telithromycin

(2011) Venkata Velvadapu et al.   JOURNAL OF ORGANIC CHEMISTRY

Synthesis of Macrocyclic Aromatic Amines via C-N Coupling Reaction

(2011) Kousuke Tsuchiya   JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN

Control of Olefin Geometry in Macrocyclic Ring-Closing Metathesis Using a Removable Silyl Group

(2011) Yikai Wang et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Review of Macrolides (Azithromycin, Clarithromycin), Ketolids (Telithromycin) and Glycylcyclines (Tigecycline)

(2011) Jerry M. Zuckerman et al.   MEDICAL CLINICS OF NORTH AMERICA

Macrocylic bisbibenzylnatural products and their chemical synthesis

(2011) David C. Harrowven et al.   NATURAL PRODUCT REPORTS

Synthesis of macrocyclic natural products by catalyst-controlled stereoselective ring-closing metathesis

(2011) Miao Yu et al.   NATURE

Synthesis of the Cytotrienin A CoreviaMetal Catalyzed C−C Coupling

(2011) Michael Rössle et al.   ORGANIC LETTERS

Cu(I)- and Ru(II)-Mediated “Click” Cyclization of Tripeptides Toward Vancomycin-Inspired Mimics

(2011) Jinqiang Zhang et al.   ORGANIC LETTERS

Bioinspired Synthesis of Hirsutellones A, B, and C

(2011) K. C. Nicolaou et al.   ORGANIC LETTERS

Stereocontrolled Synthesis of the C8–C22 Fragment of Rhizopodin

(2011) Manuel Kretschmer et al.   ORGANIC LETTERS

Total Synthesis of Hirsutellone B via Ullmann-Type Direct 13-Membered Macrocyclization

(2011) Hiromi Uchiro et al.   ORGANIC LETTERS

Synthesis of 5-Iodo-1,2,3-triazole-Containing Macrocycles Using Copper Flow Reactor Technology

(2011) Andrew R. Bogdan et al.   ORGANIC LETTERS

Enantioselective Total Synthesis of (−)-Zampanolide, a Potent Microtubule-Stabilizing Agent

(2011) Arun K. Ghosh et al.   ORGANIC LETTERS

On Resin Side-Chain Cyclization of Complex Peptides Using CuAAC

(2011) Sampat Ingale et al.   ORGANIC LETTERS

Fidaxomicin: A Macrocyclic Antibiotic for the Treatment ofClostridium difficileInfection

(2011) Jennifer S Hardesty et al.   PHARMACOTHERAPY

Diversity-oriented synthesis of macrocyclic peptidomimetics

(2011) A. Isidro-Llobet et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

Solid-phase synthesis of biaryl cyclic peptides by borylation and microwave-assisted intramolecular Suzuki–Miyaura reaction

(2011) Ana Afonso et al.   TETRAHEDRON

Total synthesis and structural revision of engelhardione

(2011) Li Shen et al.   TETRAHEDRON LETTERS

Concise Synthesis of (−)-Nakadomarin A

(2010) David B. C. Martin et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Total Synthesis of (−)-Dactylolide

(2010) Sang Young Yun et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Synthesis and antibacterial activity of novel 4-aryl-[1,2,3]-triazole containing macrolides

(2010) David Pereira et al.   BIOORGANIC & MEDICINAL CHEMISTRY LETTERS

Recent applications of ring-closing metathesis in the synthesis of lactams and macrolactams

(2010) Hani Mutlak A. Hassan   CHEMICAL COMMUNICATIONS

Tricks with clicks: modification of peptidomimetic oligomers via copper-catalyzed azide-alkyne [3 + 2] cycloaddition

(2010) Justin M. Holub et al.   CHEMICAL SOCIETY REVIEWS

Echinocandin Antifungal Drugs in Fungal Infections

(2010) Sharon C.-A. Chen et al.   DRUGS

Discovery of Vaniprevir (MK-7009), a Macrocyclic Hepatitis C Virus NS3/4a Protease Inhibitor

(2010) John A. McCauley et al.   JOURNAL OF MEDICINAL CHEMISTRY

Disulfide Cyclized Tripeptide Analogues of Angiotensin IV as Potent and Selective Inhibitors of Insulin-Regulated Aminopeptidase (IRAP)

(2010) Hanna Andersson et al.   JOURNAL OF MEDICINAL CHEMISTRY

Total Synthesis of Batatoside L

(2010) Lin Xie et al.   JOURNAL OF ORGANIC CHEMISTRY

Targeting bacterial membrane function: an underexploited mechanism for treating persistent infections

(2010) Julian G. Hurdle et al.   NATURE REVIEWS MICROBIOLOGY

Construction of the Cyclophane Core of the Hirsutellones via a RCM Strategy§

(2010) Mingzheng Huang et al.   ORGANIC LETTERS

Synthesis of the C9−C23 (C9′−C23′) Fragment of the Dimeric Natural Product Rhizopodin

(2010) Zheng Chen et al.   ORGANIC LETTERS

“Clicktophycin-52”: A Bioactive Cryptophycin-52 Triazole Analogue

(2010) Markus Nahrwold et al.   ORGANIC LETTERS

Studies directed toward the synthesis of rhizopodin: stereoselective synthesis of the C1–C15 fragment

(2010) Tushar Kanti Chakraborty et al.   TETRAHEDRON LETTERS

Synthetic studies toward potent cytostatic macrolide rhizopodin: stereoselective synthesis of the C16–C28 fragment

(2010) Tushar Kanti Chakraborty et al.   TETRAHEDRON LETTERS

Stereoselective synthesis of the decahydrofluorene core of the hirsutellones

(2010) Geoff T. Halvorsen et al.   TETRAHEDRON LETTERS

Diversity-oriented synthesis as a tool for the discovery of novel biologically active small molecules

(2010) Warren R.J.D. Galloway et al.   Nature Communications

Total Synthesis of Hirsutellone B

(2009) K. C. Nicolaou et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Click Chemistry beyond Metal-Catalyzed Cycloaddition

(2009) C. Remzi Becer et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Telavancin Disrupts the Functional Integrity of the Bacterial Membrane through Targeted Interaction with the Cell Wall Precursor Lipid II

(2009) C. S. Lunde et al.   ANTIMICROBIAL AGENTS AND CHEMOTHERAPY

Novel acylated lipo-oligosaccharides from the tubers of Ipomoea batatas

(2009) Yong-Qin Yin et al.   CARBOHYDRATE RESEARCH

Grubbs’ Ruthenium-Carbenes Beyond the Metathesis Reaction: Less Conventional Non-Metathetic Utility

(2009) Benito Alcaide et al.   CHEMICAL REVIEWS

Mitsunobu and Related Reactions: Advances and Applications

(2009) K. C. Kumara Swamy et al.   CHEMICAL REVIEWS

Telavancin: A Novel Lipoglycopeptide

(2009) Louis D. Saravolatz et al.   CLINICAL INFECTIOUS DISEASES

Medical Therapy of Acromegaly

(2009) Richard A. Feelders et al.   DRUGS

Is synthesis the main hurdle for the generation of diversity in compound libraries for screening?

(2009) Warren RJD Galloway et al.   Expert Opinion on Drug Discovery

Microtubule-Stabilizing Activity of Zampanolide, a Potent Macrolide Isolated from the Tongan Marine SpongeCacospongia mycofijiensis

(2009) Jessica J. Field et al.   JOURNAL OF MEDICINAL CHEMISTRY

Discovery of Novel 2-Aminobenzamide Inhibitors of Heat Shock Protein 90 as Potent, Selective and Orally Active Antitumor Agents

(2009) Kenneth H. Huang et al.   JOURNAL OF MEDICINAL CHEMISTRY

Synthesis of Macrocyclic β-Strand Templates by Ring Closing Metathesis

(2009) Andrew D. Abell et al.   JOURNAL OF ORGANIC CHEMISTRY

Total Synthesis of (−)-Nakadomarin A

(2009) Pavol Jakubec et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Macromolecular Engineering through Click Chemistry and Other Efficient Transformations

(2009) Brent S. Sumerlin et al.   MACROMOLECULES

Recent advances in the chemistry, biosynthesis and pharmacology of rapamycin analogs

(2009) Edmund I. Graziani   NATURAL PRODUCT REPORTS

Molecular diversity by design

(2009) Stuart L. Schreiber   NATURE

A Rapid, Asymmetric Synthesis of the Decahydrofluorene Core of the Hirsutellones

(2009) S. David Tilley et al.   ORGANIC LETTERS

Skeletally Diverse Small Molecules Using a Build/Couple/Pair Strategy

(2009) Takuya Uchida et al.   ORGANIC LETTERS

Total Synthesis of (−)-Zampanolide and Questionable Existence of (−)-Dactylolide as the Elusive Biosynthetic Precursor of (−)-Zampanolide in an Okinawan Sponge

(2009) Jun’ichi Uenishi et al.   ORGANIC LETTERS

Studies toward the total synthesis of the hirsutellones

(2009) Mingzheng Huang et al.   TETRAHEDRON LETTERS

Therapeutic monitoring of vancomycin in adult patients: A consensus review of the American Society of Health-System Pharmacists, the Infectious Diseases Society of America, and the Society of Infectious Diseases Pharmacists

(2008) M. Rybak et al.   AMERICAN JOURNAL OF HEALTH-SYSTEM PHARMACY

The Asymmetric Total Synthesis of (+)-Cytotrienin A, an Ansamycin-Type Anticancer Drug

(2008) Yujiro Hayashi et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

The Absolute Configuration of Rhizopodin and Its Inhibition of Actin Polymerization by Dimerization

(2008) Gregor Hagelueken et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Colistin and Polymyxin B in Critical Care

(2008) Argyris Michalopoulos et al.   CRITICAL CARE CLINICS

OPT-80, a macrocyclic antimicrobial agent for the treatment ofClostridium difficileinfections: a review

(2008) Michael Gerber et al.   EXPERT OPINION ON INVESTIGATIONAL DRUGS

Pentasaccharide Glycosides from the Tubers of Sweet Potato (Ipomoea batatas)

(2008) Yongqin Yin et al.   JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY

Total Synthesis of the Cyclopeptide Alkaloid Paliurine E. Insights into Macrocyclization by Ene−Enamide RCM

(2008) Mathieu Toumi et al.   JOURNAL OF ORGANIC CHEMISTRY

Total Synthesis of (−)-Dactylolide and Formal Synthesis of (−)-Zampanolide via Target Oriented β-C-Glycoside Formation

(2008) Fei Ding et al.   JOURNAL OF ORGANIC CHEMISTRY

The exploration of macrocycles for drug discovery — an underexploited structural class

(2008) Edward M. Driggers et al.   NATURE REVIEWS DRUG DISCOVERY

RCM Macrocyclization Made Practical:  An Efficient Synthesis of HCV Protease Inhibitor BILN 2061

(2008) Chutian Shu et al.   ORGANIC LETTERS

Design, Synthesis, and Self-Assembling Properties of Novel Triazolophanes

(2008) V. Haridas et al.   ORGANIC LETTERS

Isolation and structure revision of the actin-binding macrolide rhizopodin from Myxococcus stipitatus (Myxobacteria)

(2008) Rolf Jansen et al.   TETRAHEDRON LETTERS

Towards the Optimal Screening Collection: A Synthesis Strategy

(2007) Thomas E. Nielsen et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION