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2 edition of Design, synthesis and evaluation of novel C2-unsaturated pyrrolo[2,1-c][1,4]benzodiazepines found in the catalog.

Design, synthesis and evaluation of novel C2-unsaturated pyrrolo[2,1-c][1,4]benzodiazepines

Stephen John Gregson

Design, synthesis and evaluation of novel C2-unsaturated pyrrolo[2,1-c][1,4]benzodiazepines

by Stephen John Gregson

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Published by University of Portsmouth, School of Pharmacy and Biomedical Sciences in Portsmouth .
Written in English


Edition Notes

Thesis (Ph.D.) - University of Portsmouth, 1998.

StatementStephen John Gregson.
ID Numbers
Open LibraryOL16025006M

A new and efficient synthesis of the pyrrolo[2,1-c][1,4]benzodiazepine ring system has been carried out using, as a key step, an intramolecular aza Wittig reaction of the appropriately substituted. Pyrrolo[3,2-d]pyrimidine analogs of the lead compounds were designed to evaluate the effect of intramolecular hydrogen bonding (if any) mediated conformational restriction of the lead analogs 1 and (±)-2•nd 3 was designed as a regioisomer of the pyrrolo[2,3-d]pyrimidine 1 and as an isostere of the cyclopenta[d]-pyrimidine (±)-2•HCl scaffold.

  Design, Synthesis, and Preliminary Biological Evaluation of Pyrrolo[3,4‐c]quinolin‐1‐one and Oxoisoindoline Derivatives as Aggrecanase Inhibitors Andrea Cappelli Prof. E . This work reports the synthesis of novel 1,4,3,5-oxathiadiazepanes 4,4-dioxides from the reaction of N’-benzyl-N-(2-hydroxyethyl)-sarcosine or proline sulfamide with aromatic aldehydes under acid catalysis. To prepare the starting materials N-Boc-sulfamide derivatives of sarcosine or proline were alkylated with benzyl alcohol under Mitsunobu reaction conditions, the Boc group was removed.

Howard PH, Chen Z, Gregson SJ et al () Synthesis of a novel C2/C2’-aryl-substituted pyrrolo[2,1-c]-[1,4]benzodiazepine dimer prodrug with improved water solubility and reduced DNA reaction rate. The design and synthesis of the two cytotoxic derivatives 15 and 16 of the novel pyrrolo[1′,2′:1,2][1,4]diazepin[7,6-b]indol-5(6H)-one nucleus is y available methyl 2-indolecarboxylates 5 and 6 are nitrosated with NaNO 2 in AcOH to give the analogs 7 and 8, which are then oxidized with KMnO 4 in aq. NaOH to provide the 3-NO 2 acids 9 and


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Design, synthesis and evaluation of novel C2-unsaturated pyrrolo[2,1-c][1,4]benzodiazepines by Stephen John Gregson Download PDF EPUB FB2

The design, synthesis and biological evaluation of novel pyrrolo [2,1][1,4] benzodiazepine-water insoluble 31–38 and water soluble 39–46 glycosylated pyrrole and imidazole polyamide conjugates are described that involved mercuric chloride mediated cyclization of the corresponding amino diethyl thioacetals.

The compounds were prepared with varying numbers of pyrrole and imidazole containing. A series of novel pyrrolo[2,1-c][1,4]benzodiazepine (PBD) hybrids linked with indole carboxylates is described. These compounds were prepared by linking C-8 of 3 (DC) with an indole 2-carbonyl moiety (9) through carbon chain linkers to afford PBD hybrid agents 17−21 in good yields.

Preliminary in vivo tests show that these hybrid agents have potent antitumor by:   The design, synthesis and evaluation of four novel pyrrolo[2,1-c][1,4]benzodiazepine (PBD) prodrugs (1a,b and 2a,b; Fig.

1) for potential use in carboxypeptidase G2 (CPG2)-based antibody-directed enzyme prodrug therapy (ADEPT) is gh all four prodrugs were shown to be less cytotoxic than the released parent PBDs 3 and 4, the urea prodrugs 1b and 2b were found to be too Cited by:   A novel series of Hh signaling pathway inhibitors were designed by replacing the pyrimidine skeleton of our earlier reported lead compound 1 with pyrrolo[2,1-f][1,2,4]triazine ng from this new scaffold, SAR exploration was investigated based on structural modification on A-ring, C-ring and by: Design and Synthesis of a Novel Epoxide-Containing Pyrrolo[2,1-c][1,4]benzodiazepine (PBD) via a New Cyclization Procedure Stuart C.

Wilson, Philip W. Howard and David E. Thurston* Division of Medicinal Chemistry, School of Pharmacy and Biomedical Sciences, University of Portsmouth, Park Building, King Henry I Street, Portsmouth, Hants, PO1 2DZ.

The synthesis of a potential DNA-crosslinking pyrrolo[2,1-c][1,4]benzodiazepine (PBD) substituted at the C8-position with a 2,3-epoxypropaneoxy moiety using a new cyclization procedure is described.

A mild cyclization procedure involving NFmoc cleavage has been used for the synthesis of an epoxide-containing PBD. Title:1,4-Diazepines: A Review on Synthesis, Reactions and Biological Significance VOLUME: 16 ISSUE: 5 Author(s):Muhammad A.

Rashid, Aisha Ashraf*, Sahibzada S. Rehman, Shaukat A. Shahid, Adeel Mahmood and Muhammad Faruq Affiliation:Department of Chemistry, Government Postgraduate College of Science, Faisalabad, Department of Chemistry, Government College Women University. Title: Pyrrolo[2,1-c][1,4]benzodiazepine as a Scaffold for the Design and Synthesis of Anti- Tumour Drugs VOLUME: 9 ISSUE: 1 Author(s):Laura Cipolla, Ana C.

Araujo, Cristina Airoldi and Davide Bini Affiliation:Dept. of Biotechnology and Biosciences, University of Milano-Bicocca, della Scienza 2,Milano, Italy. Keywords:Anti- Tumour Drugs, Synthesis, pyrrolo[2,1-c][1,4.

A series of 7H-pyrrolo[2,3-d]pyrimidine derivatives were designed and synthesized as reversible BTK inhibitors, and evaluated their kinase selectivity, anti-proliferation against the B-cell lymphoma cell lines (Ramos, Jeko-1) and cell line BTK enhanced (Daudi) in them, compound 28a exhibited the most excellent potency (IC 50 = nM against BTK enzyme, μM.

Title:Synthesis of Benzopyran Linked Pyrrolo[2,1-c][1,4]benzodiazepines as DNA-Binding and Potential Anticancer Agents VOLUME: 9 ISSUE: 2 Author(s):Ahmed Kamal, Rajender, Methuku Kashi Reddy, Vangala Santhosh Reddy and Gajjela Bharath Kumar Affiliation:Division of Organic Chemistry, Centre for Chemical Biology, Indian Institute of Chemical Technology, Tarnaka, Hyderabad.

In this report, we described the design, synthesis and biological evaluation of a novel series of 6-substituted pyrrolo[2,3-d]pyrimidine antifolates with an isosteric replacement of the side chain amide moiety to a sulfur atom, in attempting to extend our research to develop novel multitargeted antifolates as antitumor agents.

Proline-derived 1,4-benzodiazepine-2,5-diones are extremely useful scaffolds in medicinal chemistry. In this paper, we describe a protocol for retentive C3 alkylation of these materials, thus accomplishing the direct synthesis of enantiopure quaternary 1,4-benzodiazepine-2,5-diones.

The high enantioselectivities (up to %) are attributed to memory of chirality. In this respect, the pyrrolo[2,1-c][1,4]benzodiazepines (PBDs) are of interest as they bind to guanine residues in the minor groove with a preference for Pu-G-Pu sequences.

Here we sought to evaluate the contribution of the PBD unit to the biological activity of PBD-conjugates and, to this end, an adenosine nucleoside was attached to the PBD A-ring C8 position. A convergent approach was successfully adopted for the synthesis of a novel C8-linked pyrrolo(2,1-c)(1,4)benzodiazepine(PBD)-adenosine(ADN) hybrid.

The PBD and adenosine (ADN) moieties were. Abstract: New A-C8 and C-C2-linked 6-chloropurine-pyrrolo[2,1-c][1,4]benzodiazepine hybrids have been prepared and evaluated for their anticancer potential.

The molecular modeling studies might be explained in terms of effect of the molecule on binding in the minor groove of DNA and also comparison to both A-C8/C-C2-position of the PBD. Solid-Phase Synthesis of a Library of Pyrrolo[2,1-c][1,4] Synthesis of Novel Linear Pyridinopolyamine Libraries with Potent Antibacterial Activity.

Design, Synthesis, and Evaluation of Small-Molecule Libraries. Jonathan A. Ellman. Accounts of Chemical Research 29 (3). A versatile and efficient synthesis of carbinolamine-containing pyrrolo[1,4]benzodiazepines (or the corresponding imine forms) of types 2, 7, and 8 is described that involves mercuric chloride.

There is growing interest in agents, such as the pyrrolo[2,1-c][1,4]benzodiazepines (PBDs), that can recognize and bond to specific sequences of DNA. They have potential as gene regulators with.

A member C2-aryl pyrrolo[2,1-c][1,4]benzodiazepine-5,dione (PBD dilactam) library has been synthesized using Suzuki coupling, and the effect of base upon racemisation at the C11a-position.

The synthesis of several new 4‐mono‐ and 2,4‐disubstituted pyrrolo[2,1‐f ][1,2,4]triazines is described. Key 1‐aminopyrrole‐2‐carbonitrile intermediates 3 and 15 were obtained by N ‐amination of the corresponding pyrrole‐2‐carboxaldehyde followed by CHO → CN conversion with either hydroxylamine‐ O ‐sulfonic acid for 3.

Design and Synthesis of 3, 4-Dihydropyrrolo[2, 1-c][1, 4]oxazinone and its 7-Acyl Derivatives Article in Chinese Chemical Letters 14(10) October with 17 Reads How we measure 'reads'.It is the broad spectrum of biological activities of pyrrolo[1,2-a][1,4]benzodiazepines that has maintained the interest of researchers to date whereas several derivatives of the even less studied pyrrolo[1,2-d][1,4]benzodiazepines were found to be potent non-nucleoside HIV-1 reverse transcriptase inhibitors.

The pyrrolo[2,1‐c][1,4]benzodiazepines (PBDs) are a family of sequence‐selective DNA minor‐groove binding agents that form a covalent aminal bond between their C11‐position and the C2‐NH 2 groups of guanine bases.

The first example of a PBD monomer, the natural product anthramycin, was discovered in the s, and the best known PBD dimer, SJG‐ (also known as SG, NSC .