Four cytotoxic N4-substituted thiosemicarbazones derived from 2-hydroxynaphthalene-1-carboxaldehyde

Paul V. Bernhardt; Lorraine M Caldwell; David B Lovejoy; Des R. Richardson

Four cytotoxic N4-substituted thiosemicarbazones derived from 2-hydroxynaphthalene-1-carboxaldehyde

Paul V. Bernhardt, Lorraine M Caldwell, David B Lovejoy, Des R. Richardson

Research output: Contribution to journal › Article › peer-review

Abstract

The X-ray crystal structures are reported of four novel and potentially O,N,S-tridentate donor ligands that demonstrate antitumour activity. These ligands are 1-[(4-methylthiosemicarbazono)methyl]-2-naphthol, C(13)H(13)N(3)OS, (III), 1-[(4-ethylthiosemicarbazono)methyl]-2-naphthol, C(14)H(15)N(3)OS, (IV), 1-[(4-phenylthiosemicarbazono)methyl]-2-naphthol, C(18)H(15)N(3)OS, (V), and 1-[(4,4-dimethylthiosemicarbazono)methyl]-2-naphthol dimethyl sulfoxide solvate, C(14)H(15)N(3)OS.C(2)H(6)OS, (VI). These chelators are N4-substituted thiosemicarbazones, each based on the same parent aldehyde, namely 2-zhydroxynaphthalene-1-carboxaldehyde isonicotinoylhydrazone. Conformational variations within this series are discussed in relation to the optimum conformation for metal-ion binding.

Original language	English
Pages (from-to)	629-633
Number of pages	5
Journal	Acta Crystallographica. Section C: Crystal Structure Communications
Volume	59
Issue number	Pt 11
Publication status	Published - Nov 2003
Externally published	Yes

Keywords

Antineoplastic Agents
Crystallography, X-Ray
Hydrogen Bonding
Iron Chelating Agents
Models, Molecular
Molecular Conformation
Molecular Structure
Naphthalenes
Thiosemicarbazones
Journal Article
Research Support, Non-U.S. Gov't

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title = "Four cytotoxic N4-substituted thiosemicarbazones derived from 2-hydroxynaphthalene-1-carboxaldehyde",

abstract = "The X-ray crystal structures are reported of four novel and potentially O,N,S-tridentate donor ligands that demonstrate antitumour activity. These ligands are 1-[(4-methylthiosemicarbazono)methyl]-2-naphthol, C(13)H(13)N(3)OS, (III), 1-[(4-ethylthiosemicarbazono)methyl]-2-naphthol, C(14)H(15)N(3)OS, (IV), 1-[(4-phenylthiosemicarbazono)methyl]-2-naphthol, C(18)H(15)N(3)OS, (V), and 1-[(4,4-dimethylthiosemicarbazono)methyl]-2-naphthol dimethyl sulfoxide solvate, C(14)H(15)N(3)OS.C(2)H(6)OS, (VI). These chelators are N4-substituted thiosemicarbazones, each based on the same parent aldehyde, namely 2-zhydroxynaphthalene-1-carboxaldehyde isonicotinoylhydrazone. Conformational variations within this series are discussed in relation to the optimum conformation for metal-ion binding.",

keywords = "Antineoplastic Agents, Crystallography, X-Ray, Hydrogen Bonding, Iron Chelating Agents, Models, Molecular, Molecular Conformation, Molecular Structure, Naphthalenes, Thiosemicarbazones, Journal Article, Research Support, Non-U.S. Gov't",

author = "Bernhardt, {Paul V.} and Caldwell, {Lorraine M} and Lovejoy, {David B} and Richardson, {Des R.}",

year = "2003",

month = nov,

language = "English",

volume = "59",

pages = "629--633",

journal = "Acta Crystallographica. Section C: Crystal Structure Communications",

issn = "0108-2701",

publisher = "Wiley-Blackwell, Wiley",

number = "Pt 11",

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TY - JOUR

T1 - Four cytotoxic N4-substituted thiosemicarbazones derived from 2-hydroxynaphthalene-1-carboxaldehyde

AU - Bernhardt, Paul V.

AU - Caldwell, Lorraine M

AU - Lovejoy, David B

AU - Richardson, Des R.

PY - 2003/11

Y1 - 2003/11

N2 - The X-ray crystal structures are reported of four novel and potentially O,N,S-tridentate donor ligands that demonstrate antitumour activity. These ligands are 1-[(4-methylthiosemicarbazono)methyl]-2-naphthol, C(13)H(13)N(3)OS, (III), 1-[(4-ethylthiosemicarbazono)methyl]-2-naphthol, C(14)H(15)N(3)OS, (IV), 1-[(4-phenylthiosemicarbazono)methyl]-2-naphthol, C(18)H(15)N(3)OS, (V), and 1-[(4,4-dimethylthiosemicarbazono)methyl]-2-naphthol dimethyl sulfoxide solvate, C(14)H(15)N(3)OS.C(2)H(6)OS, (VI). These chelators are N4-substituted thiosemicarbazones, each based on the same parent aldehyde, namely 2-zhydroxynaphthalene-1-carboxaldehyde isonicotinoylhydrazone. Conformational variations within this series are discussed in relation to the optimum conformation for metal-ion binding.

AB - The X-ray crystal structures are reported of four novel and potentially O,N,S-tridentate donor ligands that demonstrate antitumour activity. These ligands are 1-[(4-methylthiosemicarbazono)methyl]-2-naphthol, C(13)H(13)N(3)OS, (III), 1-[(4-ethylthiosemicarbazono)methyl]-2-naphthol, C(14)H(15)N(3)OS, (IV), 1-[(4-phenylthiosemicarbazono)methyl]-2-naphthol, C(18)H(15)N(3)OS, (V), and 1-[(4,4-dimethylthiosemicarbazono)methyl]-2-naphthol dimethyl sulfoxide solvate, C(14)H(15)N(3)OS.C(2)H(6)OS, (VI). These chelators are N4-substituted thiosemicarbazones, each based on the same parent aldehyde, namely 2-zhydroxynaphthalene-1-carboxaldehyde isonicotinoylhydrazone. Conformational variations within this series are discussed in relation to the optimum conformation for metal-ion binding.

KW - Antineoplastic Agents

KW - Crystallography, X-Ray

KW - Hydrogen Bonding

KW - Iron Chelating Agents

KW - Models, Molecular

KW - Molecular Conformation

KW - Molecular Structure

KW - Naphthalenes

KW - Thiosemicarbazones

KW - Journal Article

KW - Research Support, Non-U.S. Gov't

M3 - Article

C2 - 14605412

SN - 0108-2701

VL - 59

SP - 629

EP - 633

JO - Acta Crystallographica. Section C: Crystal Structure Communications

JF - Acta Crystallographica. Section C: Crystal Structure Communications

IS - Pt 11

ER -

Four cytotoxic N4-substituted thiosemicarbazones derived from 2-hydroxynaphthalene-1-carboxaldehyde

Abstract

Keywords

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