Literature DB >> 22544981

Hydrazine-mediated cyclization of Ugi products to synthesize novel 3-hydroxypyrazoles.

Arthur Y Shaw1, Jonathan A McLaren, Gary S Nichol, Christopher Hulme.   

Abstract

This report discloses a novel concise synthesis of a series of 3-hydroxypyrazoles 5 via a tandem Ugi/debenzylation /hydrazine-mediated cyclization sequence. Herein, n-butyl isocyanide 4b was utilized as an alternative to classical convertible isocyanides enabling high yielding hydrazine-mediated cyclization. Taken together, a novel class of 3-hydroxypyrazoles 5a-5i was synthesized with potential to be of interest in future library enrichment strategies.

Entities:  

Year:  2012        PMID： 22544981      PMCID： PMC3337763          DOI： 10.1016/j.tetlet.2012.03.033

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  16 in total

1.  Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: identification of 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benze nesulfonamide (SC-58635, celecoxib).

Authors:  T D Penning; J J Talley; S R Bertenshaw; J S Carter; P W Collins; S Docter; M J Graneto; L F Lee; J W Malecha; J M Miyashiro; R S Rogers; D J Rogier; S S Yu; E G Burton; J N Cogburn; S A Gregory; C M Koboldt; W E Perkins; K Seibert; A W Veenhuizen; Y Y Zhang; P C Isakson
Journal:  J Med Chem       Date:  1997-04-25       Impact factor: 7.446

Review 2.  "Multi-component reactions : emerging chemistry in drug discovery" 'from xylocain to crixivan'.

Authors:  Christopher Hulme; Vijay Gore
Journal:  Curr Med Chem       Date:  2003-01       Impact factor: 4.530

3.  Substituent effects of N-(1,3-diphenyl-1H-pyrazol-5-yl)benzamides on positive allosteric modulation of the metabotropic glutamate-5 receptor in rat cortical astrocytes.

Authors:  Tomas de Paulis; Kamondanai Hemstapat; Yelin Chen; Yongqin Zhang; Samir Saleh; David Alagille; Ronald M Baldwin; Gilles D Tamagnan; P Jeffrey Conn
Journal:  J Med Chem       Date:  2006-06-01       Impact factor: 7.446

Review 4.  From 2000 to mid-2010: a fruitful decade for the synthesis of pyrazoles.

Authors:  Santos Fustero; María Sánchez-Roselló; Pablo Barrio; Antonio Simón-Fuentes
Journal:  Chem Rev       Date:  2011-08-01       Impact factor: 60.622

5.  SAR of a novel 'Anthranilamide Like' series of VEGFR-2, multi protein kinase inhibitors for the treatment of cancer.

Authors:  Philip Wickens; Harold Kluender; Julie Dixon; Catherine Brennan; Furahi Achebe; Antonella Bacchiocchi; Don Bankston; Donald Bierer; Michael Brands; Debbie Braun; Melissa S Brown; Chih-Yuan Chuang; Jacques Dumas; Istvan Enyedy; Gloria Hofilena; Zhenqiu Hong; Tim Housley; Benjamin Jones; Uday Khire; Charles Kreiman; Ellalahewage Kumarasinghe; Timothy Lowinger; Ronda Ott-Morgan; Louise Perkins; Barton Phillips; Robert Schoenleber; William J Scott; Ryan Sheeler; Anikó Redman; Xiuying Sun; Ian Taylor; Lei Wang; Scott Wilhelm; Xiaomei Zhang; Mingbao Zhang; Elizabeth Sullivan; Christopher Carter; Mark Miglarese; Joan Levy
Journal:  Bioorg Med Chem Lett       Date:  2007-03-03       Impact factor: 2.823

6.  Design, synthesis and biological evaluation of some pyrazole derivatives as anti-inflammatory-antimicrobial agents.

Authors:  Adnan A Bekhit; Tarek Abdel-Aziem
Journal:  Bioorg Med Chem       Date:  2004-04-15       Impact factor: 3.641

7.  Synthesis and antibacterial activity of novel and potent DNA gyrase inhibitors with azole ring.

Authors:  Akihiko Tanitame; Yoshihiro Oyamada; Keiko Ofuji; Mika Fujimoto; Kenji Suzuki; Tomohiko Ueda; Hideo Terauchi; Motoji Kawasaki; Kazuo Nagai; Masaaki Wachi; Jun-ichi Yamagishi
Journal:  Bioorg Med Chem       Date:  2004-11-01       Impact factor: 3.641

Review 8.  Rapid assembly of molecular diversity via exploitation of isocyanide-based multi-component reactions.

Authors:  Christopher Hulme; Thomas Nixey
Journal:  Curr Opin Drug Discov Devel       Date:  2003-11

9.  A four component coupling strategy for the synthesis of D-phenylglycinamide-derived non-covalent factor Xa inhibitors.

Authors:  Scott M Sheehan; John J Masters; Michael R Wiley; Stephen C Young; John W Liebeschuetz; Stuart D Jones; Christopher W Murray; Jeffrey B Franciskovich; David B Engel; Wayne W Weber; Jothirajah Marimuthu; Jeffrey A Kyle; Jeffrey K Smallwood; Mark W Farmen; Gerald F Smith
Journal:  Bioorg Med Chem Lett       Date:  2003-07-21       Impact factor: 2.823

10.  Identification of N-(4-piperidinyl)-4-(2,6-dichlorobenzoylamino)-1H-pyrazole-3-carboxamide (AT7519), a novel cyclin dependent kinase inhibitor using fragment-based X-ray crystallography and structure based drug design.

Authors:  Paul G Wyatt; Andrew J Woodhead; Valerio Berdini; John A Boulstridge; Maria G Carr; David M Cross; Deborah J Davis; Lindsay A Devine; Theresa R Early; Ruth E Feltell; E Jonathan Lewis; Rachel L McMenamin; Eva F Navarro; Michael A O'Brien; Marc O'Reilly; Matthias Reule; Gordon Saxty; Lisa C A Seavers; Donna-Michelle Smith; Matt S Squires; Gary Trewartha; Margaret T Walker; Alison J-A Woolford
Journal:  J Med Chem       Date:  2008-07-26       Impact factor: 7.446
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  4 in total

1.  Exploiting the Divalent Nature of Isonitriles: a novel Pictet-Spengler Amidination process.

Authors:  Federico Medda; Christopher Hulme
Journal:  Tetrahedron Lett       Date:  2014-05-01       Impact factor: 2.415

2.  Applications of ortho-phenylisonitrile and ortho-N-Boc aniline for the two-step preparation of novel bis-heterocyclic chemotypes.

Authors:  Zhigang Xu; Arthur Y Shaw; Gary S Nichol; Alexandra P Cappelli; Christopher Hulme
Journal:  Mol Divers       Date:  2012-05-24       Impact factor: 2.943

3.  Aldol reactions in multicomponent reaction based domino pathways: a multipurpose enabling tool in heterocyclic chemistry.

Authors:  Zhigang Xu; Fabio De Moliner; Alexandra P Cappelli; Christopher Hulme
Journal:  Org Lett       Date:  2013-05-29       Impact factor: 6.005

4.  Tandem synthesis of highly functionalized pyrazole derivatives from terminal alkynes, sulfonyl azides, diethyl azadicarboxylate, and sodium arylsulfinates.

Authors:  Issa Yavari; Manijeh Nematpour
Journal:  Mol Divers       Date:  2012-09-16       Impact factor: 2.943
  4 in total

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