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首页> 外文学位 >I. SYNTHETIC STUDIES USING 2,4(3H,5H)-FURANDIONE. II. SYNTHESIS OF A HAPTEN FOR AMITRIPTYLINE.
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I. SYNTHETIC STUDIES USING 2,4(3H,5H)-FURANDIONE. II. SYNTHESIS OF A HAPTEN FOR AMITRIPTYLINE.

机译：I.使用2,4（3H，5H）-呋喃酮的合成研究。二。合成阿米替林的半抗原。

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摘要

Part I. Unsaturated five-membered ring lactones constitute a key structural element in certain natural products which display an unusual range of biological activity. One such member of this lactone group is 2,4(3H,5H)-furandione ((beta)-tetronic acid). The examination of the chemical versatility of this small molecule and its synthetic applicability constitute the basis of this investigation.; For this study, a reliable preparative method for 2,4(3H,5H)-furandione was needed. Such a method has been developed and is reported. A variety of 3-(arylmethylene)-2,4(3H,5H)-furandiones are prepared by the 1:1 condensation of (beta)-tetronic acid with substituted benzaldehydes. This reaction has been extended to heteroaromatic aldehydes as well. A study of the NMR of spectra of these products and (beta)-tetronic acid itself is included. The 3-(arylmethylene)-2,4(3H,5H)-furandione system is utilized to synthesize the novel condensed (10-(aryl)-4,10-dihydro-1H,3H-furo{lcub}3,4-c{rcub}-{lcub}1,5{rcub}benzothiazepin-1-one system. Further, the ring transformation of 3-(arylmethylene)-2,4(3H,5H)-furandiones to the substituted pyrazol-3-one system by reaction with hydrazines is demonstrated.; Some heteroannelation reactions of (beta)-tetronic acid with a variety of substituted 2-aminobenzophenones, 2-aminobenzaldehydes, and o-amino heteroaromatic aldehydes have been accomplished. The first 1:1 aldol condensation adduct of a ketone with (beta)-tetronic acid has been achieved using the vic-polyketones ninhydrin and alloxan.; Finally, progress towards the synthesis of the (alpha),(beta)-bisbenzylbutyrolactone lignan carbon skeleton from 2,4(3H,5H)-furandione has been accomplished.; Part II. The synthesis of 3-(3-carboxy-10,11-dihydro-5H-dibenzo-{lcub}a,d{rcub}cyclohepten-5-ylidene)-N,N-dimethyl-1-propamine as a hapten for the widely prescribed antidepressant Amitriptyline is described. This hapten was prepared for use in the development of a radioimmunoassay for Amitriptyline. It can be successfully coupled to human serum albumin and illicits a satisfactory antibody response when injected into laboratory animals.
机译：第一部分：不饱和五元环内酯是某些天然产物中的关键结构元素，这些天然产物显示出异常的生物活性范围。该内酯基团的一个这样的成员是2，4（3H，5H）-呋喃二酮（β-tetronicacid）。该小分子的化学多功能性及其合成适用性的检验构成了这项研究的基础。对于本研究，需要一种可靠的2,4（3H，5H）-呋喃丹酮的制备方法。已经开发并报道了这种方法。通过将β-tetronic酸与取代的苯甲醛进行1：1缩合，可制得各种3-（芳基亚甲基）-2,4（3H，5H）-呋喃二酮。该反应也已经扩展到杂芳族醛。包括对这些产物和β-tetronic酸本身的光谱的NMR的研究。利用3-（芳基亚甲基）-2,4（3H，5H）-呋喃二酮体系合成新型的缩合的（10-（芳基）-4,10-二氢-1H，3H-呋喃基[lcub} 3,4- c {rcub}-{lcub} 1,5 {rcub}苯并噻唑-1-酮体系进一步将3-（芳基亚甲基）-2,4（3H，5H）-呋喃二酮环转化为取代的吡唑-3-证明了与肼反应的一种系统；已经完成了β-四氢元件酸与各种取代的2-氨基二苯甲酮，2-氨基苯甲醛和邻氨基杂芳族醛的杂化反应，第一个1：1的醛醇缩合反应已使用vic-聚酮茚三酮和四氧嘧啶实现了酮与β-tetronic酸的加合物;最后，从2,4（3H）合成了α，β-双苄基丁内酯木脂素碳骨架已完成；，5H）-呋喃二酮；第二部分。3-（3-羧基-10,11-二氢-5H-二苯并-{lcub} a，d {rcub}环庚基-5-亚烷基）-N的合成，N-二甲基-1-丙胺为w的半抗原描述了适当处方的抗抑郁药阿米替林。该半抗原被制备用于阿米替林的放射免疫测定。它可以成功地与人血清白蛋白偶联，并且在注入实验动物时会产生令人满意的抗体反应。

著录项

  • 作者

    SCHMIDT, DIANE GROB.;

  • 作者单位

    University of Cincinnati.;

  • 授予单位 University of Cincinnati.;
  • 学科 Chemistry Organic.
  • 学位 Ph.D.
  • 年度 1981
  • 页码 208 p.
  • 总页数 208
  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 有机化学;
  • 关键词

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