Propyl Derived

N-ethyl kanamycin A (153) has some resistance to APH(3 ), ANT(2 ), and AAC(3). Butakacin [59733-86-7] C22H N 0 2 t i l-A/-(3)-2-hydroxy-4-aminobutyl derivative of kanamycin A (154), has antimicrobial properties similar to amikacin. A similar effect was seen with the l-A/-(l,3-dihydroxy-2-propyl) derivative of kanamycin B, propikacin [66887-96-5] C22H42N 022 (155). Methylation of the 6 -amine reduces susceptibility to AAC(6 ) (156). 

ICA(238)179). Further reaction of the l,3-di- o-propyl-derivative with water gives the dinuclear species 24. 

If reaction 49 is responsible for the high decomposition yield of ASCO, it can be understood why it does not occur for PSCO, since the C—H bond strength in the allyl compound is weaker than in the propyl derivative due to the resonance stabilization of the radical60. However, the yield of alanine was found to be 1.97 in the case of radiolysis of PCSO and almost zero for ACSO. Thus reaction 49 does not occur for the case of ACSO. Since only the yields of cysteine (0.98 for ACSO and 0 for PCSO) are given, no explanation can be proposed for the high decomposition yield of ACSO. 

Thiophenolate complexes have been discussed, however, a considerable amount of alkylthiolate zinc chemistry is also known. The zinc alkylthiolate complexes with methanethiolate, ethanethiolate, and /. so-propylthiolate have been synthesized and characterized as precursors for ZnS formation. Thermolysis studies demonstrated the formation of ZnS and release of dimethylsulfide. Reactivity was similar with only the rm-propyl derivative showing much slower reaction.523 The polyzincate Zni0S4(SEt)i2L4 is a well-characterized neutral zinc sulfur compound.524... 

Polymer formation is still observed with some sterically hindered thiolates, 2,4,6-Ao-propyl thiophenolate, and 2,4,6-trimethyl thiophenolate complexes have been studied. They can be synthesized by the reaction of Zn[N(SiMe3)2]2 with the appropriate arene chalcogenol. With the least steric bulk, the trimethyl derivative forms coordination polymers that can only be dissolved in strongly coordinating solvents. The iso-propyl derivative is more soluble forming oligomers in solution. 1... 

There are two different relative orientations of X and a y-carbon atom in staggered n-propyl derivatives. Accordingly, we have to make a distinction between y-gauche (yg-SCS) and y-antiperiplanar (ya-SCS) substituent effects. 

In principle, the approach outlined above for the a-oxoamides can be applied to any reaction, ground or excited state, which converts an achiral reactant into a chiral product, and Toda, Tanaka, and coworkers have investigated a wide variety of such processes [ 15,16]. A complete discussion of their work is beyond the scope of this review, and we illustrate the general approach taken with one final example. As shown in Scheme 4, irradiation of crystalline complexes of ene-diones 20a-f with chiral host (R,R)-(-)-9b led to cyclized products 21a-f in the variable yields and ee values indicated in Table 1 [22]. Remarkably, for reasons that were not clear (there was no accompanying X-ray crystallography), the R=n-propyl derivative 20g was found to give a completely different photoproduct, spiro compound 22 (69% yield, 97% ee, stereochemistry unknown), a result that once again illustrates the rather capricious nature of the use of chiral hosts for asymmetric induction. 

Cyclic thioureas such as 2-thiouracil 1118 (R = H), its 6-methyl 1118 (R = Me) and 6-propyl derivatives 1118 (R = Pr), as well as thiobarbital 1119 are effective agents against hyperthyroidism, while thiamylal 1120 is used as an anesthetic. A large number of barbituric acid derivatives have hypnotic or sedative effects, and allobarbital 1121 (R = R = allyl), aprobarbital 1121 (R = allyl, R = r-Pr), cyclobarbital 1121 (R = Et, R = 1-cyclohexenyl), pentobarbital 1121 (R = Et, R = 2-pentyl), phenobarbital 1121 (R = Et, R = Ph), propallyonal 1121 (R = isopropyl, R = 2-bromoallyl), and secobarbital 1121 (R = allyl, R = 2-pentyl) are all examples of N-unsubstituted barbiturates, while hexobarbital 1122 represents an N-methylated derivative. 

Unusual pteridine alkaloids including 224-226 have been identified from sponges Clathria spp.) collected off Argentina <2002T4481>. The pteridines, which are 6(2 -hydroxypropyl) and 6-propyl derivatives of 1,3-dimethyl-lumazine, are linked to a core tryptophan through an ester and 1-, 2-, or 4-alkylation, respectively. 

The homologues C3H 7CsCCHjOH and C5H] jCsCCI OH may be prepared by a similar procedure. In the case of the propyl derivative, more extractions with Et2[Pg.58]

Extremely active compounds are found among 2-aminotetralines. 6,7-Dihydroxy-2-aminotetraline (4.85, ADTN) and its A-(n-propyl) derivative are well-studied 2-aminotetraline derivatives. Nomifensine (4.83) is related to these aminotetralines and is used as an antidepressant drug. The catechol analog of nomifensine (with two hydroxyls on the 4-phenyl ring) is also a potent inhibitor of NE and DA uptake. 

N-Alkylation of 3,3-diethyl-l,3,4,6,7,llb-hexahydro-2//-pyrimido-[2,l-a]isoquinoline-2,4-dione (95, R = R1 = Et, R2 = H) with 3-(dimethylamino)propyl chloride in dioxane in the presence of sodium hydride (53% in oil) gave the l-(3-dimethylamino)propyl derivative (69YZ649. 

Two Russian papers359,360 have described the synthesis and addition of acetylenic esters to dihydro-s-triazines. The triphenyl derivative 281 on heating with DEAD in ether for 3 hours gave 80% of286, presumably via 285. The diphenyl propyl derivative (282) added Michael fashion to... 

A third dimer was obtained from Norway sprucewood in somewhat impure condition (m.p., 117°-127°C.). However, its vapor phase retention time and ultraviolet spectrum 23) were identical with those of authentic 5,5 -diethyl-2,2 -dihydroxy-3,3 -dimethoxybiphenyl (VII), m.p. = 143°C. (P). Furthermore, the NMR spectrum and melting point of its purified diacetate were identical with those of the synthetic compound. The corresponding 5,5 -di-w-propyl derivative has already been isolated from neutral hydrogenation of softwood lignin in our laboratory 18). 

WOP2007/054296) over Pd/C (10%) for 5-70 h gave 9-(3-substi-tuted propyl) derivatives. 

---