{"title":"甾体吲哚酮及其衍生物的合成","authors":"F. Kamau","doi":"10.4314/ECAJPS.V8I3.9725","DOIUrl":null,"url":null,"abstract":"5&alpha-Androstan-17&beta-ol-3-one condenses with 2-nitrobenzaldehyde in alkaline conditions to give the steroidal indoxyl 17&beta-hydroxy-1-(3′-oxoindan-2′-yliden)-3-nor-1,2-secoandrostan-3-oic acid (I) which on refluxing with acetic anhydride affords the lactam 17&beta-acetoxy-3′-aza-4a-homoandrost-1-eno-(3,2-a)-indan-3′,4-dione (II). Reduction of I with sodium borohydride gives the indole 17&beta-hydroxy-1-(indol-2′-yl)-3-nor-1, 2-secoandrostan-3-oic acid (III). The results of this synthesis suggest that 3-ketosteroids saturated in ring A react in a similar manner to 17-ketosteroids, with 2-nitrobenzaldehyde.\n\n Keywords : Synthesis, Steroidal Indoxyl, derivatives. The East and Central African Journal of Pharmaceutical Sciences Vol. 8 (3) 2005: pp. 43-44","PeriodicalId":22387,"journal":{"name":"The East and Central African Journal of Pharmaceutical Sciences","volume":"57 1","pages":"45-49"},"PeriodicalIF":0.0000,"publicationDate":"2007-10-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis of Steroidal Indoxyl, and Derivatives from 3-ketosteroid\",\"authors\":\"F. Kamau\",\"doi\":\"10.4314/ECAJPS.V8I3.9725\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"5&alpha-Androstan-17&beta-ol-3-one condenses with 2-nitrobenzaldehyde in alkaline conditions to give the steroidal indoxyl 17&beta-hydroxy-1-(3′-oxoindan-2′-yliden)-3-nor-1,2-secoandrostan-3-oic acid (I) which on refluxing with acetic anhydride affords the lactam 17&beta-acetoxy-3′-aza-4a-homoandrost-1-eno-(3,2-a)-indan-3′,4-dione (II). Reduction of I with sodium borohydride gives the indole 17&beta-hydroxy-1-(indol-2′-yl)-3-nor-1, 2-secoandrostan-3-oic acid (III). The results of this synthesis suggest that 3-ketosteroids saturated in ring A react in a similar manner to 17-ketosteroids, with 2-nitrobenzaldehyde.\\n\\n Keywords : Synthesis, Steroidal Indoxyl, derivatives. The East and Central African Journal of Pharmaceutical Sciences Vol. 8 (3) 2005: pp. 43-44\",\"PeriodicalId\":22387,\"journal\":{\"name\":\"The East and Central African Journal of Pharmaceutical Sciences\",\"volume\":\"57 1\",\"pages\":\"45-49\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2007-10-24\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"The East and Central African Journal of Pharmaceutical Sciences\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.4314/ECAJPS.V8I3.9725\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"The East and Central African Journal of Pharmaceutical Sciences","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.4314/ECAJPS.V8I3.9725","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Synthesis of Steroidal Indoxyl, and Derivatives from 3-ketosteroid
5&alpha-Androstan-17&beta-ol-3-one condenses with 2-nitrobenzaldehyde in alkaline conditions to give the steroidal indoxyl 17&beta-hydroxy-1-(3′-oxoindan-2′-yliden)-3-nor-1,2-secoandrostan-3-oic acid (I) which on refluxing with acetic anhydride affords the lactam 17&beta-acetoxy-3′-aza-4a-homoandrost-1-eno-(3,2-a)-indan-3′,4-dione (II). Reduction of I with sodium borohydride gives the indole 17&beta-hydroxy-1-(indol-2′-yl)-3-nor-1, 2-secoandrostan-3-oic acid (III). The results of this synthesis suggest that 3-ketosteroids saturated in ring A react in a similar manner to 17-ketosteroids, with 2-nitrobenzaldehyde.
Keywords : Synthesis, Steroidal Indoxyl, derivatives. The East and Central African Journal of Pharmaceutical Sciences Vol. 8 (3) 2005: pp. 43-44
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