Iodination methods for routine preparation of 17-123I-heptadecanoic acid and 15-(123I-phenyl)-pentadecanoic acid

The diagnosis of the myocardial diseases with 17¹²³I-heptadecanoic acid and recently 15-(p-¹²³I-phenyl)-pentadeconoic acid has been applied successfully. A high labeling yield and short reaction time is desired for routine applications. The over-all yield of the complete procedure is the most important consideration. Different labeling approaches were evaluated to increase the yield of the entrire procedure. So each laboratory is able to select the method appropriate for their individual demands and possibilities.     

Kinetics of 17-(123I) iodoheptadecanoic acid in myocardium of rats

Myocardial uptake and turnover of 17-(¹²³I)-iodoheptadecanoic acid, injected i.v., was studied in rats. Kinetics of radioactivity incorporated into myocardial tissue and heart lipids as well as myocardial radioactivity recovered as¹²³I iodide were determined. Maximal heart uptake of IHA (7.9% dose/g heart) was observed as early as 30 sec., p.i., followed by mono-component elimination period. Already 10 to 30 sec p.i. 70 to 80% of total myocardial radioactivity was recovered as¹²³I iodide. IHA was incorporated only in modest amounts into myocardial phospholipids and triglycerides. Time course of total myocardial radioactivity grossly paralleled that recovered as¹²³I iodide. These findings indicate stringent limitations in utility of IHA as a tracer for assessment of β-oxidation.     

Comparative evaluation of labelling patterns and turnover of lipids,tagged by 15 /p-123I-phenyl-/ pentadecanoic and 1-14C-palmitic acid

Uptake and turnover of chloroform/methanol extractable tissue lipids labelled in vivo simultaneously with 15/p-¹²³I-phenyl-/pentadecanoic and l-¹⁴C-palmitic acid were compared. Lipid turnover studies were performed in fasted pentobarbital-anaesthetized Wistar rats in tissues with highly varying free fatty acid turnover rates. In all tissues investigated, i.e. heart, lung, liver, spleen and kidneys, both tracers labelled nearly identical lipid fraction. Main tracer uptake was found in free fatty acids, phospholipids, diglycerides and triglycerides. A highly significant correlation of uptake and turnover in main tissue lipid fraction indicated an essentially identical metabolic pathway of both tracers in intermediary tissue lipid metabolism. Concordant tracer uptake and turnover patterns in tissue of lipids with highly varying free fatty acid metabolic rates suggested that intrinsic metabolic activity of the tissue and respective lipid fraction was the major determinant of metabolic handling of both iodophenyl fatty- and palmitic acid. Thus, the feasibility of iodophenylpentadecanoic acid as free fatty acid tracer for studying tissue lipid metabolism is demonstrated.     

3-[P-(P-(P-甲氧基苯乙炔基)苯乙炔基)苯氧基]丙烯酸丙酯合成与表征

以对甲氧基苯乙炔、对溴苯酚、3-氯-1-丙醇和甲基丁炔醇等为原料,通过williamson反应、Sonogashina和酯化等反应合成3[P-(P-(P-甲氧基苯乙炔基)苯乙炔基)苯氧基]丙烯酸丙酯.用元素分析,IR和1HNMR等手段对产物的组成和结构进行了表征,并讨论反应物量、催化剂等因素对产率的影响.     

A new chiral acid for the resolution of racemic bases : (s)-(-)-(2-phenylcarbamoyloxy)propionic acid (carbamalactic acid)

(S)-(?)-Carbamalactic acid is the phenylcarbamate derived from natural (S)-lactic acid. This new chiral reagent was efficiently used for the resolution of racemic bases such as α-methylbenzylamine, ephedrine and α-(l-naphthyl)ethylamine.     

A new intermediate for the rapid synthesis of N-isopropyl-p-/125I/- or p-/123I/ amphetamine

The triazene derivative of N-isopropylamphetamine XI, has been prepared in seven steps from amphetamine, as a new intermediate which is readily converted to N-isopropyl-p-iodoamphetamine /XII/. XI makes now possible the simple, rapid and regiospecific synthesis of /¹²⁵I/- or /¹²³I/-XII direct before the application.     

Synthesis of the sialic acid (-)-KDN and certain epimers from (-)-3-dehydroshikimic acid or (-)-quinic acid

(-)-3-Dehydroshikimic acid (3-DHS, 4), a C(7)-building block now available in large quantity from corn syrup, has been converted into the sialic acid (-)-KDN (3) as well as its C-7- and C-8-epimers. (-)-Quinic acid can be used for the same purpose. [structure: see text]     

有机电致红光材料 4-(二腈亚甲叉)-2-甲基-6-(4-二甲胺基-苯乙烯)-4H-吡喃的合成新方法

设计全新的路线合成了红光材料4-(二腈亚甲叉)-2-甲基-6-(4-二甲胺基-苯乙烯)-4H-吡喃(DCM)。采用具有烯烃骨架的β-苯基丙烯酸酯为中间体先引入双键,再经过三酮合环制备乙烯基吡喃。     

Development of a process for routine production of123I using the127I(p, 5n)123Xe→123I reaction

The object of this paper is to give details of a production method for¹²³I, now in routine use at Harwell. We employ the (p, 5n) reaction, irradiating a liquid target of di-iodomethane (CH₂I₂) spiked with additional iodine, with 58 MeV protons. A yield of ∼9 mCi/μAh is obtained; the only detectable radionuclidic impurity is¹²⁵I, present to the extent of ∼0.15% by activity at the time of separation of Xe from I.     

Synthesis of 15-(4-[11C]methylphenyl)pentadecanoic acid (MePPA) via Stille cross-coupling reaction

For experimental studies by animal PET [¹¹C]-labeled 15-(4-methylphenyl)pentadecanoic acid (MePPA) is an attractive alternative to the radioiodinated 15-(4-iodophenyl)pentadecanoic acid (IPPA) which has widely been used for imaging of fatty acid metabolism. The important physiological aspect is that the iodine atom and the methyl substituent have similar steric and lipophilic properties. For preparation of [¹¹C]MePPA, Stille cross-coupling reaction was applied since the same tin precursor as for the radiosynthesis of IPPA and readily available [¹¹C]CH₃I can be used. Unsaturated tris(dibenzylideneacetone)dipalladium(0)/tri(o-tolyl)phosphine [Pd₂(dba)₃/P(o-tolyl)₃] was taken as the catalytic system. The reaction conditions were optimized with respect to temperature, time, solvent and amount of precursor. The best radiochemical yields of 73 ± 2.8% (decay corr.) were obtained using 0.525 mg tin precursor in DMF at 80 °C already after a reaction time of 10 min. The labeled methyl ester was hydrolyzed by 1 M NaOH/EtOH at 80 °C within 3 min to give [¹¹C]IPPA in a RCY of 62 ± 3.0%. The radiochemical purity of the product assured by HPLC was >99% and the overall preparation time including HPLC purification and formulation was 40 min.     

On the methylation of 5-(4-alkoxyphenyl)-15-(4-pyridyl)porphyrins

Mixed condensation of 3,3′-diethyl-4,4′-dimethyl-2,2′-dipyrrolylmethane 1 with 4-formylpyridine 2 and 4-alkoxybenzaldehyde 3 in acid medium and subsequent oxidation of the reaction mixture with DDQ gives, among other compounds, title compound 5 . An efficient methylation procedure of the pyridyl group in 5-(4-alkyoxyphenyl)-15-(4-pyridyl)porphyrins is described. Mixed condensation of 1 with N-methyl-4-formylpyridinium salt 9 and 3 yields among other compounds 5-(4-N-methylpyridiniumiodide)porphyrin 10 .     

Development of delta(15)N stratification of NO(3)(-) in soil profiles

New evidence, obtained using a robust method for measuring the delta(15)N of NO(3)(-)-N in soil, is consistent with denitrification being the major determinant in the vertical distribution of NO(3)(-)-delta(15)N in soil profiles. These data also suggest that varying moisture regimes result in different effects of soil NO(3)(-)-N leaching on residual whole soil delta(15)N.     

Asymmetric total synthesis of 14(R),15(S)-, 14(S),15(R)-, 14(R),15(R)-, and 14(S),15(S)-epoxyeicosatrienoic acids

The four chiral stereoisomers of 14,15-oxido-5Z, 8Z, 11Z-eicosatrienoic acid were synthesized. The absolute stereochemistry in each case was derived from an asymmetric epoxidation of E-2-octen-1-ol.     

Synthesis and properties of 5-(p-carbomethoxyphenyl)- 15-(p-dimethylaminophenyl)porphyrin

An unsymmetrically substituted 5,15-diarylporphyrin 1 , with p-dimethylamino and p-carbomethoxy substituents, was synthesized via a MacDonald condensation of aryldipyrromethane precursors 6 and 12 , which were prepared in good yield by three or four step procedures starting from ethyl 3,4-dimethyl-1H-pyrrole-2-carboxylate ( 2 ).     

Synthesis of poly(acrylic acid) (PAA) modified Pluronic P123 copolymers for pH-stimulated release of doxorubicin

Pluronic P123 was chain-extended at their terminal groups using atom transfer radical polymerization to form poly(acrylic acid) (PAA) tails and obtain the PAA-b-P123-b-PAA (P123-PAA) copolymer. The incorporation of PAA had the effect of increasing the carrier's drug loading capacity of an anti-cancer drug, Doxorubicin (DOX), and also allowed for pH-controlled release of the drug. Drug release assays showed that up to 60% of DOX cargo could be retained in the DOX/P123-PAA complex for 3 days at normal physiological pH (7.4). This was then followed by a secondary burst release of DOX when the environment became more acidic (pH 5). Therefore, it was possible that the more acidic physiological environment of tumor sites could be used to trigger an accelerated release of DOX from the drug carriers. The material was demonstrated for potential application in the delivery of cationic drugs for cancer treatment.     

Preparation of123I-α-(p-iodoanilino)phenylacetonitrile using HPLC

Synthesis of α-(p-iodoanilino)phenylacetonitrile (IAPAN), an amygdalin analog, labeled with I-123 (t1/2 13.3 hr) in a carrier-free state (i.e. no-carrier-added) was made possible by virtue of the high speed, sensitivity, and resolving power of HPLC. Aniline was iodinated by the action of no-carrier-added Na¹²³I in the presence of Cu(II), and the resulting iodaniline was reacted with benzaldehyde followed by the addition of HCN to yield the title compound. The radioactive IAPAN was separated from α-anilinophenylacetonitrile and other byproducts by reversed phase partition chromatography on an octadecylsilane column using 50% ethanol/H₂O as eluent. The product was correlated with authentic, classically characterized IAPAN, and with¹²³I IAPAN prepared by electrophilic exchange of IAPAN and ICl iodination of α-anilinophenylacetonitrile.     

Oxidation with p-(Methoxycarbonyl)perbenzoic acid 2. Oxidation of nitrogen heterocycles to the N-oxides

Conclusions We have examined the oxidation of various nitrogen heterocycles to the N-oxides with p-(methoxycarbonyl)perbenzoic acid.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2337–2339, October, 1978.Part 1 [1].Deceased.