Salicylic acid derivative

Table 9. Physical Properties of Salicylic Acid Derivatives...

KOLBE - SCHMIDT Salicylic Acid Synthesis Caiboxylation (usually ortho) of phenols. Industrial method to obtain salicylic acid derivatives... 

Phenolic resins were the first totally synthetic plastics invented. They were commercialized by 1910 [I]. Their history begins before the development of the structural theory of chemistry and even before Kekule had his famous dreams of snakes biting their tails. It commences with Gerhardt s 1853 observations of insoluble resin formation while dehydrating sodium salicylate [2]. These were followed by similar reports on the behavior of salicylic acid derivatives under a variety of reaction conditions by Schroder et al. (1869), Baeyer (1872), Velden (1877), Doebner (1896 and 1898), Speyer (1897) and Baekeland (1909-1912) [3-17]. Many of these early reports appear to involve the formation of phenolic polyesters rather than the phenol-aldehyde resins that we think of today. For... 

Finally, attachment of a rather complex side chain to the para position of the benzene ring on the sulfonamide leads to the very potent, long-acting oral antidiabetic agent, glyburide (215). Preparation of this compound starts with the chlorosul-fonation of the acetamide of 3-phenethylamine (209). The resulting sulfonyl chloride (210) is then converted to the sulfonamide (211) and deacylated (212). Reaction with the salicylic acid derivative, 213, in the presence of carbodiimide affords the amide, 214. Condensation of that with cyclohexylisocyanate affords glyburide (215). ... 

The salicylic acid functionality incorporated in a rather complex molecule interestingly leads to a compound that exhibits much the same activity as the parent. The 1,4 diketone required for formation of the pyrrole ring can be obtained by alkylation of the enamine from 2-tetralone (38) with phenacyl bromide. Condensation of the product, 39, with salicylic acid derivative 40 leads to the requisite heterocyclic system (41). The acid is then esterified (42) and the compound dehydrogenated to the fully aromatic system (43). Saponification affords fendosal (44). ... 

The CB sheet is coated on the back with microcapsules 5 to 10 pm in diameter, in which leuco dye solution in a nonvolatile solvent is contained. The CF sheet is coated on the front with an acidic coreactant such as reactive clay, zinc salt of salicylic acid derivatives, zinc-modified phenolic resin, etc. On the application of pressure, the microcapsule is ruptured in the area delineated by the pressure pattern, and the leuco dye solution is thereby transferred to the CB sheet to bring about a color-forming reaction with acidic coreactant resulting in a distinct image on the surface of the CF sheet. By inserting a middle sheet (or sheets) called the CFB sheet, which is coated on the front and back with acidic coreactant and microcapsules, respectively, multiple copies can be obtained. 

The CF sheet is prepared by coating an acidic coreactant such as naturally occurring reactive clay, zinc salt of salicylic acid derivatives and zinc modified phenolic resin. 

At present, the relevance of these results to photode-gradationl 0f condensates 1 is a matter of speculation. Of particular interest is identification of the photoproduct quencher(s) (PP, Scheme I). Possible candidates are salicylic acid derivatives, which exhibit the requisite absorptivity at about 300 nm, and which may be formed by oxidation of ortho-photo-Fries products (Scheme III), as illustrated in eq. 1. 

Despite the many simple methods for preparation of carboxylic esters and thioesters, in some instances, use of 1-acylbenzotriazoles 915 as O and S acylating agents may be advantageous. For example, easy to prepare salicylic acid derivative 941 reacts with cyclopentanol under microwave irradiation to give 92% yield of cyclopentyl salicylate in 10 min <2006JOC3364>. In another example, L-phenylalanine derivative 942 reacts with benzyl mercaptan... 

The interaction of ligands derived from salicylic acid and its derivatives has been extensively investigated (83, 147, 149, 160, 170, 176, 183-205). A similar situation obtains with regard to l-hydroxy-2-naphthoic acid (185, 194, 196, 198, 206-215). Salicylic acid derivatives may be useful in chelation therapy for beryllium poisoning (2). 

Salicylic acid derivatives, 22 11—25 physical properties of, 22 18t Salicylic acid esters, 22 12-17 physical properties of, 22 13-15t Salicylic acid salts... 

Technically important dyes are salicylic acid derivatives that function as chrome mordant dyes for wool. Thus Cl Mordant Blue 1 (6.187) is made by the aldehyde synthesis from 2,6-dichlorobenzaldehyde and 2-hydroxy-3-methylbenzoic (o-cresotinic) acid in concentrated sulphuric acid. Oxidation of the leuco base is achieved by the addition of sodium nitrite. On wool the product, which is isolated as the sodium salt, is a dull maroon colour, changing to a bright blue on treatment with a chromium salt. Some dyes of this type, such as Cl Mordant Violet 1 (6.188), also contain a basic group. This compound is also prepared by the aldehyde route. 

Intramolecular general acid catalysis in reactions of salicylic acid derivatives 196 Why are EM s for general acid-base catalysed reactions so low 198 EM and the nature of the transition state 200 The formation of small rings 205... 

INTRAMOLECULAR GENERAL ACID CATALYSIS IN REACTIONS OF SALICYLIC ACID DERIVATIVES... 

Fig. 9.7 Tethering with extenders on caspase-3. The extender (3) covalently modifies the protein and can then be deprotected to reveal a thiol for Tethering. One of the strongest hits is the salicylic acid derivative shown.

Prenylated salicylic acid derivatives, including 3-famesyl-2-hydroxy-benzoic acid (Fig. 7) isolated from the leaves of Piper multiplinervium C. DC. (Piperaceae) showed mii-Helicobacter pylori activity at MIC 37.5 pg/mL Boropinic acid (Fig. 7), an active constituent isolated from Boronia pinnata (Fam. Rutaceae) had activity against HP with an MIC value of 1.62 pglmL Five novel compounds, psoracorylifols A-E (1-5) with important activity against Helicobacter pylori MICs 12.5-25 pg/mL were isolated from a well-known traditional Chinese medicine (TCM), the seeds of Psoralea corylifolia by Yin et al 2006. 

Salicin (42) Aminosalicylic acid (43) Salicylic acid derivative An t i tuberc u losis... 

Salicin (42) Aspirin (44) Salicylic acid derivative Analgesic... 

Salicin (42) Mesalamine (45) Salicylic acid derivative Ulcerative colitis... 

El. Kakemi, K., Arita, T., Yamashina, H., and Konishi, R., Absorption and excretion of drugs X. The effect of the protein binding on the renal excretion rate of salicylic acid derivatives. Yakugaku Zasshi 82, 536-639 (1962). 

In medical practice, other salicylic acid derivatives are used in the form of salts. Magnesium salicylate and sodium salicylate are less effective than respective doses of aspirin however, they are easier on patients that are sensitive to aspirin. Choline magnesium trisalicylate represents a mixture of choline salicylate and magnesium salicylate, which has the same effect as aspirin however, it is easier on patients in which gastrointestinal effects are observed upon taking aspirin. 

Anthranylic acid derivatives are direct structural analogs of salicylic acid derivatives. They possess analgesic, anti-inflammatory, and fever-reducing activity. They are similar to... 

Acetylsalicylic ac/cf. Acetylsalicylic acid has been associated with Reye s syndrome. Because diflunisal is a salicylic acid derivative, the possibility of its association with Reye s syndrome cannot be excluded. 

Fluorinated NSAIDs are present in all the main families of nonspecific COX inhibitors arylacetic acid derivatives, anthranilic acid derivatives, and salicylic acid derivatives. 

Mechanism of Action A salicylic acid derivative that locally inhibits arachidonic acid metabolite production, which is increased in patients with chronic inflammatory bowel disease. Therapeutic Effect Blocks prostaglandin production and diminishes inflammation in the colon. 

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