Ueber eine neue Klasse von Farbstoffen

Fischer, Otto; Rudolph, Ch.

doi:10.1002/cber.18820150212

Cited by 13 publications

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“…However, barbituric acid per se does not possess CNS activity, probably due to its lower lipophilicity compared to its alkyl or aryl derivatives, namely the barbiturates. Fischer and von Mering (1903) employed a condensation reaction to synthesize barbituric acid, using diethyl malonic acid and urea; this was not only a practical method for synthesizing barbiturates but was also coupled with the revolutionary discovery that barbital possesses hypnotic properties. Having visited Verona earlier, von Mering thought it appropriate to name the new compound after this city; thus barbital became Veronal.…”

Section: Phenobarbitalmentioning

confidence: 99%

How did phenobarbital’s chemical structure affect the development of subsequent antiepileptic drugs (AEDs)?

Bialer¹

2012

Epilepsia

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Summary Phenobarbital has been in clinical use as an antiepileptic drug (AED) since 1912. The initial clinical success of phenobarbital and other barbiturates affected the design of subsequent AEDs (e.g., phenytoin, primidone, ethosuximide), developed between 1938 and 1962, the chemical structures of which resemble that of phenobarbital. However, the empirical discovery of carbamazepine (1962) and the serendipitous discovery of valproic acid (1967) led to subsequent AEDs having chemical structures that are diverse and completely different from that of phenobarbital. Sixteen AEDs were introduced between 1990 and 2012. Most of these AEDs were developed empirically, using mechanism‐unbiased anticonvulsant animal models. The empirical nature of the discovery of these AEDs, coupled with their multiple mechanisms of action, explains their diverse chemical structures. The antiepileptic market is therefore crowded. Future design of new AEDs must have a potential for treating nonepileptic central nervous system (CNS) disorders (e.g., bipolar disorder, neuropathic pain, migraine prophylaxis, or restless legs syndrome). The barbiturates were once used as sedative‐hypnotic drugs, but have been largely replaced in this role by the much safer benzodiazepines. In contrast, phenobarbital is still used worldwide in epilepsy. Nevertheless, the development of nonsedating phenobarbital derivatives will answer a clinical unmet need and might make this old AED more attractive.

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Section: Phenobarbitalmentioning

confidence: 99%

How did phenobarbital’s chemical structure affect the development of subsequent antiepileptic drugs (AEDs)?

Bialer¹

2012

Epilepsia

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“…It was not until 1903 that the first therapeutically useful barbiturate drug became available in the form of 5,5-diethylbarbituric acid (barbital) or Veronal ® and this pharmaceutical was widely prescribed as a sedative-hypnotic [442]. Thereafter hundreds of derivatives of barbituric acid were prepared and tested for their usefulness as therapeutic agents.…”

Section: Barbituratesmentioning

confidence: 99%

Handbook of Drug Interactions

Karalliedde¹,

Henry²

2012

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PrefaceAdverse drug reactions and drug interactions remain a major issue in 2011. During the second edition of our book, FDA reported greater than 370,000 serious adverse events in 2009 and more than 100,000 for the first quarter of 2010. The Adverse Event Reporting System is a database that gives computerized statistics used to support FDA's post-marketing safety surveillance for all approved drugs. A serious event is defined as requiring hospitalization, being life-threatening, causing disability or congenital anomalies, for example. Importantly, more than 63,000 deaths were recorded in 2009, and more than 20,000 occured during the first quarter of 2010.The second edition of Handbook of Drug Interactions: A Clinical and Forensic Guide has been updated to reflect new information and also includes new chapters of interest. In this respect, it is a continuation of the first edition and part of the ongoing story of drug-drug interactions.Pharmacogenomics is a rapidly growing field covering the genetic basis for individual variability in drug responses. This new section allows the reader to review important polymorphisms in drug metabolizing enzymes and applies the findings to forensic interpretation through interesting cases involving opiates.Although the section relating to central nervous system drugs encompasses a number of potential drugs with illicit use such as benzodiazepines and opiates, a chapter dealing exclusively with drugs of abuse has been added to the second edition. Cocaine, amphetamines, cannabis, flunitrazepam and GHB are now discussed. Alcohol and nicotine are still covered in the section related to environmental and social pharmacology.The existing chapters from the first edition have, in most cases, been updated and edited to reflect new data or bring out better tables and diagrams. More recent drugs and formulations are included. Recent references have been added for completeness. This volume emphasizes explanations when possible and covers both pharmacokinetic and pharmacodynamic drug interactions. The result, we hope, will continue to prove useful to health and forensic professionals as well as students.

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TheFriedländer Synthesis of Quinolines

1982

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Friedländer prepared quinoline in 1882 by the condensation of o ‐aminobenzaldehyde with acetaldehyde in the presence of sodium hydroxide. This type of reaction has since been extensively explored and, in its most general form, can be defined as an acid‐ or base‐catalyzed condensation followed by a cyclodehydration between an o ‐amino‐substituted aromatic aldehyde, ketone, or derivative thereof with an appropriately substituted aldehyde, ketone, or other carbonyl compound containing a reactive α‐methylene group. Some quinolines can also be prepared simply by heating a mixture of the reactants with or without a solvent. Because both reactants contain a carbonyl group, certain quinolines can be prepared from a single starting compound. Of historic interest is the formation of the dye flavaniline from acetanilide. When acetanilide is heated with zinc chloride, the acetyl group of some molecules migrates to the ortho position, and that of others migrates to the para position. The resulting mixture of o ‐acetylaniline and p ‐acetylaniline then undergoes Friedländer condensation to form flavaniline. Two related quinoline syntheses, the Pfitzinger reaction and the Niementowski reaction, can be considered as extensions of the Friedländer synthesis. The Pfitzinger reaction uses an isatic acid or isatin and the Niementowski reaction uses an anthranilic acid for condensation to form a 4‐quinolinecarboxylic acid and a 4‐hydroxyquinoline, respectively. Several other related reactions, such as the Combes quinoline synthesis, the Doebner–Miller quinoline synthesis, and the Skraup quinoline synthesis, use different types of starting compounds. It is of interest that all of the six aforementioned syntheses of quinolines were discovered within a period of 14 years in the latter part of the nineteenth century, undoubtedly reflecting many scientific interests and commercial activities at that time, including the isolation of quinolines from coal tar, the manufacture of dyes, and studies of natural products such as alkaloids.

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Ueber eine neue Klasse von Farbstoffen

Cited by 13 publications

References 0 publications

How did phenobarbital’s chemical structure affect the development of subsequent antiepileptic drugs (AEDs)?

How did phenobarbital’s chemical structure affect the development of subsequent antiepileptic drugs (AEDs)?

Handbook of Drug Interactions

TheFriedländer Synthesis of Quinolines

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