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Synthesis of the rotenoids 6-deoxyclitoriacetal isolated from roots of Stemona collinsae Craib. and cytotoxic activity against cancer cell lines

หน่วยงาน จุฬาลงกรณ์มหาวิทยาลัย

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ชื่อเรื่อง : Synthesis of the rotenoids 6-deoxyclitoriacetal isolated from roots of Stemona collinsae Craib. and cytotoxic activity against cancer cell lines
นักวิจัย : Prapas Khorphueng
คำค้น : Cytotoxicity , Stemona collinsae
หน่วยงาน : จุฬาลงกรณ์มหาวิทยาลัย
ผู้ร่วมงาน : Sophon Roengsumran , Amorn Petsom , Chulalongkorn University. Faculty of Science
ปีพิมพ์ : 2548
อ้างอิง : 9741417845 , http://cuir.car.chula.ac.th/handle/123456789/7932
ที่มา : -
ความเชี่ยวชาญ : -
ความสัมพันธ์ : -
ขอบเขตของเนื้อหา : -
บทคัดย่อ/คำอธิบาย :

Thesis (Ph.D.)--Chulalongkorn University, 2005

The total synthesis of 6-deoxyclitoriacetal (39), a cytotoxic natural product, has been achieved by using PtCl[subscript2]-catalyzed hydroarylation, Sharpless asymmetric dihydroxylation, IBX regioselective diol oxidation and stereoselective intramolecular keto-aldehyde pinacol coupling as the key steps. The important steps of this synthesis began with the conversion of compund 1,2-dimethoxy-4-prop-2-ynyloxybenzene (75) into 6,7-dimethoxy-2H-chromene (83) using PtCl[subscript2]-catalyzed hydroarylation reaction successfully in good yield. The Sharpless asymmetric dihydroxylation of compound 83 provided a diol 84 which was converted into 3-hydroxy-6,7-dimethoxy-chroman-4-one (82) by selective oxidation with IBX in EtOAc. Conversion of [alpha]-hydroxy ketone 82 to a good leaving group, Tf (86), leaded to connection of D ring and A-B ring which was convinced by S[subscript N]2 reaction in very good yield (80%). The C ring was formed by SmI[subscript2]-promoted intramolecular Pinacol-type cyclization of 2-(6,7-dimethoxy-4-oxo-chroman-3-yloxy)-6-hydroxy-4-methoxybenzaldehyle (87) which was delivered the right stereogenic center at C 12a. Finally, completed synthesis of 6-deoxyclitoriacetal (39) was achieved by oxidation of 2,3,9-trimethoxy-6,6a-dihydro-12H-chromeno[3,4-b]chromene-11,12,12a-triol (88) with MnO[subscript2]. The compound 39 exhibited cytotoxic activity against human breast carcinoma (BT474), lung carcinoma (CHAGO), hepato carcinoma (HEP-G2), gastric carcinoma (KATO3) and colon carcinoma (SW620) at IC50 0.2, 0.9, 0.1, 0.3 and 0.1 [microgram]/mL, respectively.

บรรณานุกรม :
Prapas Khorphueng . (2548). Synthesis of the rotenoids 6-deoxyclitoriacetal isolated from roots of Stemona collinsae Craib. and cytotoxic activity against cancer cell lines.
    กรุงเทพมหานคร : จุฬาลงกรณ์มหาวิทยาลัย.
Prapas Khorphueng . 2548. "Synthesis of the rotenoids 6-deoxyclitoriacetal isolated from roots of Stemona collinsae Craib. and cytotoxic activity against cancer cell lines".
    กรุงเทพมหานคร : จุฬาลงกรณ์มหาวิทยาลัย.
Prapas Khorphueng . "Synthesis of the rotenoids 6-deoxyclitoriacetal isolated from roots of Stemona collinsae Craib. and cytotoxic activity against cancer cell lines."
    กรุงเทพมหานคร : จุฬาลงกรณ์มหาวิทยาลัย, 2548. Print.
Prapas Khorphueng . Synthesis of the rotenoids 6-deoxyclitoriacetal isolated from roots of Stemona collinsae Craib. and cytotoxic activity against cancer cell lines. กรุงเทพมหานคร : จุฬาลงกรณ์มหาวิทยาลัย; 2548.