Pharmacochemistry of 1,3-indandiones:
Gespeichert in:
| Weitere Verfasser: | |
|---|---|
| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
Amsterdam [u.a.]
Elsevier
1981
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| Schriftenreihe: | Pharmacochemistry library
3 |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | XVII, 346 S. |
Internformat
MARC
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| 040 | |a DE-604 |b ger |e rakwb | ||
| 041 | 0 | |a eng | |
| 049 | |a DE-188 | ||
| 245 | 1 | 0 | |a Pharmacochemistry of 1,3-indandiones |c ed. by W. Th. Nauta ... |
| 264 | 1 | |a Amsterdam [u.a.] |b Elsevier |c 1981 | |
| 300 | |a XVII, 346 S. | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 490 | 1 | |a Pharmacochemistry library |v 3 | |
| 700 | 1 | |a Nauta, Wybe Thomas |4 edt | |
| 830 | 0 | |a Pharmacochemistry library |v 3 |w (DE-604)BV001899371 |9 3 | |
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Datensatz im Suchindex
| _version_ | 1804144800794935296 |
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| adam_text | IMAGE 1
PHARMACOCHEMISTRY LIBRARY
EDITORS: W.TH. NAUTA AND R.F. REKKER
VOLUME 3
PHARMACOCHEMISTRY
OF 1,3-INDANDIONES
EDITED BY WTH.NAUTAAND R.F REKKER
DEPARTMENT OF PHARMACOCHEMISTRY, FREE UNIVERSITY, AMSTERDAM, THE
NETHERLANDS
UNIVERSITATS- BLBLIOTHEK
ELSEVIER SCIENTIFIC PUBLISHING COMPANY
AMSTERDAM - OXFORD - NEW YORK 1981
IMAGE 2
VII
CONTENTS
CONTRIBUTORS XIII
LIST OF CONSULTED RUSSIAN MONOGRAPHS AND PROCEEDINGS XIV
PREFACE XV
GENERAL INTRODUCTION XVII
CHAPTER 1. SYNTHESIS AND CHEMICAL PROPERTIES OF 1,3-INDANDIONES 1
1.1. INTRODUCTION 1
1.2. SYNTHETIC METHODS F OR THE 1,3-INDANDIONE SKELETON 1
1.2.1. CYCLIZATION OF THE FIVE-MEMBERED RING FROM AN *»*:* :.;- D I S U
B S T I T U T ED ARYL COMPOUND 1
1 . 2 . 1 . 1. FROM 2-A-OXO-SUBSTITUTED BENZOIC ESTERS 2
1.2.1.2. CONDENSATION OF PHTHALIC ESTERS 3
1.2.1.3. REARRANGEMENT OF METHYLENE PHTHALIDES 5
1.2.2. CYCLIZATION OF SUBSTITUTED BENZOYLACETIC ESTERS 12
1.2.3. CYCLIZATION WITH MALONYL CHLORIDE 13
1.2.4. 1,3-INDANDIONES FROM COMPOUNDS CONTAINING THE INDANE RING
SYSTEM 13
1.2.5. REARRANGEMENT OF NAPHTHOQUINONE COMPOUNDS 14
1.3. SYNTHESIS OF 2-SUBSTITUTED 1,3-INDANDIONES 15
1.3.1. SYNTHESIS OF 2-SUBSTITUTED 1,3-INDANDIONES BY REACTION AT
THE C 2 ATOM 15
1 . 3 . 1 . 1. E L E C T R O P H I L IC S U B S T I T U T I ON 15
1 . 3 . 1 . 1 . 1. A L K Y L A T I ON 15
1.3.1.1.2. INTERACTION WITH CARBONYL GROUPS 22
1.3.1.1.3. ARYLATION AND PHENYLIODONATION 27
1.3.1.1.4. ACYLATION 29
1.3.1.1.5. HALOGENATION 30
1.3.1.1.6. N I T R A T I O N, N I T R O S A T I O N, DIAZO COUPLING AND
SULFONATION 31
1.3.1.2. NUCLEOPHILIC S U B S T I T U T I ON 34
1.3.2. SYNTHESIS OF 2-SUBSTITUTED 1,3-INDANDIONES BY REACTION OF
2-YL IDENE-1,3-INDANDIONES 36
1 . 3 . 2 . 1. REDUCTION 36
1 . 3 . 2 . 2. ADDITION 37
1.3.2.3. NUCLEOOHILIC SUBSTITUTION 38
IMAGE 3
V I II
1.3.3. SYNTHESIS OF 2-SUBSTITUTED 1,3-INDANDIONES BY REACTION
IN THE 2-SUBSTITUENT 39
1.3.3.1. INTRODUCTION 39
1.3.3.2. 2-SATURATED ALKYL-1,3-INDANDIONES 39
1.3.3.3. 2-UNSATURATED ALKYL-1,3-INDANDIONES 43
1.3.3.4. 2-ACYL-L,3-INDANDIONES 45
1.3.3.5. 2-AMINO-L,3-INDANDIONES 47
1.4. GENERAL CHEMICAL PROPERTIES 49
1.4.1. INTERACTION WITH THE CARBONYL GROUPS 49
1.4.2. OXIDATION 57
1.4.3. REDUCTION 63
1.4.4. IRRADIATION 55
1.5. TYPICAL REACTION OF 1,3-INDANDIONE COMPOUNDS 66
1.5.1. AUTOCONDENSATION AND DIMERIZATION 66
1.5.2. REACTION OF NINHYDRIN AND 1,2,3-INDANTRIONE 68
1.5.3. REARRANGEMENTS 72
1.5.3.1. REARRANGEMENT TO SIX-MEMBERED CARBOCYCLIC RINGS . . .. 72
1.5.3.2. REARRANGEMENT TO NITROGEN-CONTAINING SIX-MEMBERED
RINGS 73
1.5.3.3. REARRANGEMENT TO FIVE- OR FOUR-MEMBERED RINGS 75
1.5.4. TYPICAL REACTIONS OF 2-NITRO-L,3-INDANDIONE 76
1.6. LABELLED 1,3-INDANDIONES 76
REFERENCES 78
CHAPTER 2. PHYSICO-CHEMICAL ASPECTS OF 1,3-INDANDIONES 91
2.1. INTRODUCTION 91
2.2. INFRARED SPECTROSCOPY 92
2 . 2 . 1. DIKETO FORM 92
2 . 2 . 1 . 1. 2-ARYLIDENE-1,3-INDANDIONES 94
2.2.1.2. TRANSMISSION OF SUBSTITUENT EFFECTS 101
2.2.1.3. DIKETO-FORM 2-ARYL-1,3-INDANDIONES 104
2.2.2. ENOL FORM 105
2.2.3. 2-ACYL- AND 2-AROYL-L,3-INDANDIONES 107
2.3. ELECTRONIC ABSORPTION SPECTROSCOPY 108
2.3.1. 2-ARYL-L,3-INDANDIONES 109
2.3.2. HMO CALCULATIONS 115
2.3.3. 2-ARYLIDENE-1,3-INDANDIONES 121
2.3.4. 2-ACYL- AND 2-AROYL-1,3-INDANDIONES 124
2.4. NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY 125
2.4.1. 2-ARYL-L,3-INDANDIONES 125
IMAGE 4
IX
2.4.2. 2-DIARYLMETHYL-L,3-INDANDIONES 135
2.4.3. 2-ARYLIDENE-L,3-INDANDIONES 142
2.5. A C I D I T Y, TAUTOMERISM AND D I S T R I B U T I ON 144
2 . 5 . 1. STERIC EFFECTS ON ENOLIZATION 146
2.5.2. ELECTRONIC EFFECTS ON P. ;: AND ENOLIZATION 147
A
2.5.3. D I S T R I B U T I ON BETWEEN TWO IMMISCIBLE SOLVENTS 157
2.6. ELECTROCHEMICAL ASPECTS 163
2 . 6 . 1. POLAROGRAPHIC REDUCTION OF 2-PHENYL-1,3-INDANDIONE AND
RELATED COMPOUNDS 163
2.6.2. DETECTION OF FREE RADICALS IN THE REDUCTION OF
1,3-INDANDIONES 168
2.6.3. POLAROGRAPHIC REDUCTION OF 2-ARYLIDENE-1,3-INDANDIONES . . . 169
2.6.4. ELECTROCHEMICAL OXIDATION OF 2-ARYL-1,3-INDANDIONES . . .. 171
2.6.5. HMO CALCULATIONS 173
2.6.6. MISCELLANEOUS 176
2.7. APPENDIX: DIPOLE MOMENTS AND HUCKEL PARAMETERS 177
REFERENCES 180
CHAPTER 3. BIOLOGICAL A C T I V I T I ES OF 1,3-INDANDIONES 187
3 . 1. INTRODUCTION 187
3.2. PHARMACODYNAMIC PROPERTIES 188
3 . 2 . 1. ANTICOAGULANT A C T I V I TY 188
3 . 2 . 1 . 1. INTRODUCTION 188
3.2.1.2. FORMATION OF F I B R IN 188
3.2.1.3. SIGNIFICANCE OF VITAMIN K 190
3.2.1.4. DETERMINATION OF ANTICOAGULANT A C T I V I TY 190
3.2.1.5. QUALITATIVE S T R U C T U R E - A C T I V I TY RELATIONSHIPS OF
VITAMIN K ANTAGONISTS 191
3.2.1.6. MECHANISM OF VITAMIN K ANTAGONISM 199
3.2.1.7. METABOLISM AND PHARMACOKINETICS OF 2-ARYL-L,3-INDANDIONES 201
3 . 2 . 1 . 7 . 1. ABSORPTION 202
3.2.1.7.2. D I S T R I B U T I ON 202
3.2.1.7.3. BIOTRANSFORMATION AND ELIMINATION 203
3.2.2. ANTI-INFLAMMATORY A C T I V I TY 205
3 . 2 . 2 . 1. INTRODUCTION 205
3.2.2.2. INFLAMMATION 205
3.2.2.3. QUALITATIVE S T R U C T U R E - A C T I V I TY ASPECTS ?07
3 . 2 . 2 . 3 . 1. ANTI-INFLAMMATORY A C T I V I TY OF 1,3-INDANDIONES .
. 207
3.2.2.3.2. SUBSTITUTION AT THE 2-PHENYL RING 207
3 . 2 . 2 . 3 . 3. SUBSTITUTION AT THE BENZO RING 209
IMAGE 5
3.2.2.3.4. SUBSTITUTION OF THE ACIDIC PROTON 210
3.2.2.3.5. ALTERATION OF THE 2-ARYL GROUP 210
3.2.2.3.6. MISCELLANEOUS 212
3.2.2.4. SIDE-EFFECTS 212
3.2.2.5. MODE OF ACTION 213
3.2.3. A N T I A L L E R G IC A C T I V I TY 214
3 . 2 . 3 . 1. INTRODUCTION 214
3.2.3.2. QUALITATIVE S T R U C T U R E - A C T I V I TY ASPECTS 216
3.2.3.3. MODE OF ACTION 219
3.2.4. URICOSURIC AND DIURETIC A C T I V I TY 220
3.2.5. CENTRAL NERVOUS SYSTEM A C T I V I TY 223
3 . 2 . 5 . 1. ANTIEPILEPTIC A C T I V I TY 223
3.2.6. DIVERSE PHARMACODYNAMIC PROPERTIES 227
3 . 2 . 6 . 1. NEUROMUSCULAR BLOCKING A C T I V I TY 227
3.2.6.2. GANGLIONIC BLOCKING A C T I V I TY 228
3.2.6.3. ANTINOCICEPTIVE (ANALGESIC) A C T I V I TY 228
3.2.6.4. ANTIHISTAMINE A C T I V I TY 230
3.2.6.5. CHOLERETIC A C T I V I TY 231
3.2.6.6. HYPOLIPIDAEMIC A C T I V I TY 234
3.3. BIOCIDAL PROPERTIES 236
3 . 3 . 1. ANTIMICROBIAL A C T I V I TY 236
3 . 3 . 1 . 1. ANTIBACTERIAL PROPERTIES 236
3.3.1.2. FUNGICIDAL A C T I V I TY 237
3.3.1.3. A N T I V I R AL A C T I V I TY 238
3.3.2. BIOCIDAL A C T I V I TY IN A NARROWER SENSE 239
3 . 3 . 2 . 1. RODENTICIDAL A C T I V I TY 239
3.3.2.2. CHIROPTICIDAL A C T I V I TY 241
3.3.2.3. MOLLUSCICIDAL A C T I V I TY 242
3.3.2.4. INSECTICIDAL A C T I V I TY 242
3.3.2.5. M I T I C I D AL (ACARICIDAL) A C T I V I TY 246
3 . 3 . 2 . 5 . 1. INTRODUCTION 246
3.3.2.5.2. QUALITATIVE S T R U C T U R E - A C T I V I TY ASPECTS 247
3.4. GROWTH-REGULATING A C T I V I T I ES 250
3.5. BIOCHEMICAL PROPERTIES 254
3 . 5 . 1. I N H I B I T I ON OF HYDROLYTIC ENZYMES 254
3.5.2. INTERACTION WITH PROTEINS 255
3.5.3. UNCOUPLING OF OXIDATIVE PHOSPHORYLATION 257
3.5.4. I N H I B I T I ON OF PROSTAGLANDIN SYNTHESIS 260
3.5.5. I N H I B I T I ON OF METHAEMOGLOBIN REDUCTASE 260
REFERENCES . . . .. 263
IMAGE 6
XI
CHAPTER 4. QUANTITATIVE S T R U C T U R E - A C T I V I TY RELATIONSHIPS
IN 2 - A R Y L- 1,3-INDANDIONES 271
4 . 1. INTRODUCTION 271
4.2. PARAMETERS FOR THE DESCRIPTION OF 1 I P O P H I L I C I TY AND
ELECTRONIC
AND S T E R IC EFFECTS 272
4 . 2 . 1. L I P O P H I L I C I TY 272
4.2.2. ELECTRONIC PARAMETERS 273
4.2.3. STERIC PARAMETERS 273
4.3. AN ANALYSIS OF ORTHO-SUBSTI TUTION EFFECTS 274
4 . 3 . 1. THE FUJITA-NISHIOKA EQUATION 274
4.3.2. ADAPTABILITY OF THE FUJITA-NISHIOKA EQUATION FOR INCLUSION
OF ADDITIONAL DATA POINTS; U T I L I TY OF CHARTON S I-, AND V
PARAMETERS , 276
4.4. QUANTITATIVE S T R U C T U R E - A C T I V I TY RELATIONSHIPS 280
4 . 4 . 1. UNCOUPLING A C T I V I T I ES ON OXIDATIVE PHOSPHORYLATION BY
2-DIARYLMETHYL-L,3-INDANDIONES 280
4 . 4 . 1 . 1. HANSCH APPROACH 280
4.4.1.2. APPLICATION OF FREE-WILSON AND FUJITA-BAN MODELS . . . 291
4.4.1.3. SOME CONCLUDING CONSIDERATIONS 295
4.4.2. ANTICOAGULANT A C T I V I T I ES OF
2-DIARYLMETHYL-1,3-INDANDIONES 297
4.4.3. I N H I B I T I ON OF 0-GLUCURONIDASE BY 2-DIARYLMETHYL-
1,3-INDANDIONES 300
4.4.4. S T A B I L I Z A T I ON OF BSA AGAINST HEAT DENATURATION BY 2 -
A R Y L- 1,3-INDANDIONES 303
4.4.5. I N H I B I T I ON OF PROSTAGLANDIN BIOSYNTHESIS BY 2 - A R Y L-
1,3-INDANDIONES 308
4.4.6. M I T I C I D AL A C T I V I T I ES OF 2-ARYL-L,3-INDANDIONES AND
T H E IR
ACYLATED ENOL DERIVATIVES 310
4.4.7. BIOLOGICAL A C T I V I T I ES OF THE S T R U C T U R A L LY
RELATED
PYROPHTHALONES 319
4 . 4 . 7 . 1. ANTICOAGULANT A C T I V I T I ES OF .-SYROPHTNALONES L
].Q
4 . 4 . 7 . 2. A N T I H I S T A M I NE A C T I V I T I ES OF . - A N I
I N O A LT VL P Y O N H T N A L O N ES V2 L
4 . 4 . 8. A N T I - I N F L A M M A T O RY A C T I V I T I ES OF 2 - A
R Y L - 1 , 3 - I N D A N D I O N ES AND
SOME H E T E R O C Y C L IC D E R I V A T I V ES -.21
REFERENCES V 1-
APPENDIX A. THE USE OF A D J U S T ED .** AND ,* V A L U ES IN N U L T I
N LE R E G R E S S I ON
A N A L Y S IS
APPENDIX B. FREE-WILSON MODEL :: ;!
SUBJECT INDEX - :,?
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| spelling | Pharmacochemistry of 1,3-indandiones ed. by W. Th. Nauta ... Amsterdam [u.a.] Elsevier 1981 XVII, 346 S. txt rdacontent n rdamedia nc rdacarrier Pharmacochemistry library 3 Nauta, Wybe Thomas edt Pharmacochemistry library 3 (DE-604)BV001899371 3 GBV Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=021889040&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Pharmacochemistry of 1,3-indandiones Pharmacochemistry library |
| title | Pharmacochemistry of 1,3-indandiones |
| title_auth | Pharmacochemistry of 1,3-indandiones |
| title_exact_search | Pharmacochemistry of 1,3-indandiones |
| title_full | Pharmacochemistry of 1,3-indandiones ed. by W. Th. Nauta ... |
| title_fullStr | Pharmacochemistry of 1,3-indandiones ed. by W. Th. Nauta ... |
| title_full_unstemmed | Pharmacochemistry of 1,3-indandiones ed. by W. Th. Nauta ... |
| title_short | Pharmacochemistry of 1,3-indandiones |
| title_sort | pharmacochemistry of 1 3 indandiones |
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