2-hydroxy analog

When unsubstituted, C-5 reacts with electrophilic reagents. Thus phosphorus pentachloride chlorinates the ring (36, 235). A hydroxy group in the 2-position activates the ring towards this reaction. 4-Methylthiazole does not react with bromine in chloroform (201, 236), whereas under the same conditions the 2-hydroxy analog reacts (55. 237-239. 557). Activation of C-5 works also for sulfonation (201. 236), nitration (201. 236. 237), Friede 1-Crafts reactions (201, 236, 237, 240-242), and acylation (243). However, iodination fails (201. 236). and the Gatterman or Reimer-Tieman reactions yield only small amounts of 4-methyl-5-carboxy-A-4-thiazoline-2-one. Recent kinetic investigations show that 2-thiazolones are nitrated via a free base mechanism. A 2-oxo substituent increases the rate of nitration at the 5-position by a factor of 9 log... 

Similar to their 2-hydroxy analogs, these compounds exhibit properties (cf. Chapter VII) that are characteristic of each of the two possible tautomeric forms the thiol (163a) and the thione or 2-thioxo-A-4-thiazoline (163b). 

Goswami, K.P. and Green, R.E. Microbial degradation of the herbicide atrazine and its 2-hydroxy analog in submerged soils. 

Either silver acetate (64JCS2760) or hot water <81H(15)213> may be used to convert 2-bromoquinolizinium bromide to the 2-hydroxy analog in excellent yield (Scheme 60). By far the most extensive application of this or any bromoquinolizinium salt has been in the preparation of AT-substituted 2-aminoquinolizinium salts (70JMC554). A similar reaction of 2-bromo-l-hydroxyquinolizinium bromide and arylamines has been patented... 

Montgomery and Freed (1964) reviewed the early research metabolism of triazine herbicides by plants and concluded that there was a good correlation between resistance in plants and the extent of their metabolism. A common pathway of degradation for these chemicals was indicated by the presence of 2-hydroxy analogs. 

Goswami, K.P. and R.E. Green. Microbial Degradation of the Herbicide Atrazine and Its 2-Hydroxy Analog in Submerged Soils, Environ. Sci. TechnoL, 5(5) 426-429 (1971). 

Methylmercaptopropionaldehyde is also used to make the methionine hydroxy analog CH2SCH2CH2CH(OH)COOH [583-91 -5] which is used commercially as an effective source of methionine activity (71). AH commercial syntheses of methionine and methionine hydroxy analog are based on the use of acrolein as a raw material. More than 170,000 tons of this amino acid are produced yearly (30) (see Amino acids). One method for the preparation of methionine from acrolein via 3-methyhnercaptopropionaldehyde is as follows. 

The reduction of the 16-keto function in kryptogenin (66) is a good example for the selectivity of sodium borodeuteride. The resulting 16a-di-16y -hydroxy analog (67) can then be cyclized to give a Iba-d -spirostane derivative (68). ... 

The acetoxy dienone (218) gives phenol (220). Here, an alternative primary photoreaction competes effectively with the dienone 1,5-bonding expulsion of the lOjS-acetoxy substituent and hydrogen uptake from the solvent (dioxane). In the case of the hydroxy analog (219) the two paths are balanced and products from both processes, phenol (220) and diketone (222), are isolated. In the formation of the spiro compound (222) rupture of the 1,10-bond in the dipolar intermediate (221) predominates over the normal electron transmission in aprotic solvents from the enolate moiety via the three-membered ring to the electron-deficient carbon. While in protic solvents and in 10-methyl compounds this process is inhibited by the protonation of the enolate system in the dipolar intermediate [cf. (202), (203)], proton elimination from the tertiary hydroxy group in (221) could reverse the efficiencies of the two oxygens as electron sources. 

Bromo-6-phenyl-s-tetrazine (334) gives the 3-hydroxy analog in quantitative yield after a few minutes at 95° in ethanolic potassium hydroxide or ethanolic ethoxide. As with other highly activated alkoxy-azines (cf. Section III,B,4,c and reference 582), the latter... 

Addition of a hydroxyl group to the aromatic ring of ephedrine as well as changing the substitution on nitrogen leads to a compound whose main activity is to raise blood pressure. Thus, lormation of the Shiff base of the m-hydroxy analog of 30 with bcnzylamine (34), followed by catalytic reduction, yields metar- uiiinol (35). When optically active hydroxyketone is employed in... 

Scheme 64 CM with vinyl boronate 327 in novel syntheses of epo490 (240d) and 11 -hydroxy analogs 332 and 333 of epoD [146]...

COMMENT I was surprised by the results with the N-hydroxy compounds, because a number of years ago N-hydroxy-p-toluylamphetamine was studied, and it was found that it was identical to ptoluylamphetamine in its properties because it was actually rapidly and essentially quantitatively converted to p-toluylamphetamine. You are finding that the N-hydroxy analog of MDMA is not MDMA-like in its properties. These data suggest that they certainly are not metabolized in a similar way, perhaps. 

RESPONSE I did not show that the N-hydroxy analog of MDA is not MDMA-like. I showed that it is not amphetamine-like. 

Compound 24 represents a series of potent spiropiperidine GlyT-1 inhibitors that showed significant binding to the p opioid and nociceptin/ orphanin FQ peptide (NOP) receptors [67]. The hydroxy analog 25 demonstrated improved selectivity and N-propyl analog 26 exhibited increased microsomal stability but reduced GlyT-1 potency (EC50 = 450 nM) [68]. 

B) to 90% B in 3.80 min was used, then returned to 20% B at 3.81 min with equilibration until 4.2 min. In the Acquity experiment, the gradient was from 0.25 min (20% B) to 90% B in 1.65 min, maintained at 90% B through 1.90 min, then returned to 20% at 1.91 min with equilibration until 2.10 min. When an injection volume of 30 fiL (from a reconstituted solution volume of 150, uL) was used, the Shimadzu experiment yielded a typical response for 0.955 pg of deslorata-dine and 1.05 pg of its 3-hydroxy analog. In the Acquity experiment, 15 fxL of injection volume was necessary to achieve significantly better signal-to-noise ratio compared to the Shimadzu experiment representing an LLOQ of 0.478 pg for desloratadine and 0.525 pg for the 3-hydroxy metabolite. 

In a control experiment, the peak widths with UPLC were found at 0.15 min and at 0.16 min for desloratadine and its 3-hydroxy analog, respectively. The corresponding values from the Shimadzu experiment were 0.37 min and 0.32 min, respectively. Nevertheless, only a marginal improvement in sensitivity (peak height) was found under UPLC conditions. The accuracy and precision values for the two drugs under the two sets of LC conditions were very similar. 

The H+ and NH forms of homoionic montmorillonite promote the hydrolysis of chloro-s-triazines to the hydroxy analogs (hydroxy-s-triazines) (73). Apparently, the surface acidity of these clays was extremely high, since no degradation was observed in control experiments conducted at pH 3.5 in homogeneous aqueous solution. Russell et al. (73) suggested that the hydroxy-s-triazine products were stabilized in the protonated form at the silicate surface. The IR spectra of these surface complexes agreed with the spectra obtained in 6N HC1, and it was inferred that the pH at the clay surface was 3 to 4 units lower than that measured in suspension. 

Green Sunfish Dieldrin and hydroxy analogs Water Tissues 5... 

Dichloro-biphenyl Frog 3-Hydroxy analog and other phenols Water Tissues 8... 

Chemical/Physical. Hydrolyzes to the 6-hydroxy analog, especially in the presence of strong acids and alkalies (Hartley and Kidd, 1987). 

The primary ozonation by-products of atrazine (15 mg/L) in natural surface water and synthetic water were deethylatrazine, deisopropylatrazine, 2-chloro-4,6-diamino-s-triazine, a deisopropylatrazine amide (4-acetamido-4-amino-6-chloro-5-triazine), 2-amino-4-hydroxy-6-isopropylamino-5-triazine, and an unknown compound. The types of compounds formed were pH dependent. At high pH, low alkalinity, or in the presence of hydrogen peroxide, hydroxyl radicals formed from ozone yielded 5-triazine hydroxy analogs via hydrolysis of the Cl-Cl bond. At low pH and low alkalinity, which minimized the production of hydroxy radicals, dealkylated atrazine and an amide were the primary byproducts formed (Adams and Randtke, 1992). 

Hydroperoxy compounds 29 and 30 are reduced in high yields to their hydroxy analogs by triphenylphosphine. ... 

---