Hindawi Publishing Corporation Journal of Chemistry Volume 2013, Article ID 961201, 9 pages http://dx.doi.org/10.1155/2013/961201 Research Article Synthesis of (±)-Pisonivanone and Other Analogs as Potent Antituberculosis Agents A. Vasu Babu, 1 A. Rambabu, 1 P. V. Giriprasad, 2 R. Surya Chandra Rao, 1 and B. Hari Babu 1 1 Department of Chemistry, Acharya Nagarjuna University, Nagarjunanagar, Andhrapadesh, Guntur 522510, India 2 Department of Microbiology, Sri Venkateswara University, Andhrapadesh, Tirupati 517502, India Correspondence should be addressed to B. Hari Babu; dr.b.haribabu@gmail.com Received 29 June 2012; Accepted 16 September 2012 Academic Editor: Shino Homma-Takeda Copyright © 2013 A.Vasu Babu et al. is is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. A new class of alkylated chalcones and �avanones was synthesised and screened for antituberculosis, antixoidant, and cytotoxic activities. e desired compounds were synthesised using methyl substituted 2-hydroxyacetophenone as a key intermediate. e acetophenone derivative having methyl substitution was prepared in turn from methtylated phloroglucinol by formylation (by Vilsmeier-Haack reaction), followed by reduction with Wolf-Kishnner approach, and �nally acetylation was involved. Among 17 compounds, compound 5 and compound 4a inhibited M. tuberculosis at minimum inhibitory concentration (MIC) in the range between 25 g/mL and 50 g/mL. e remaining other 15 compounds also potently inhibited M. tuberculosis at MIC in range between 50 g/mL and 100 g/mL. Some of these compounds also showed moderate antioxidant and cytotoxic activities. 1. Introduction A survey of the literature revealed that many �avonoids bene�t human health [1]. Among these large class of com- pounds some of the alkylated �avonoids isolated from plants also act as antimalarial [2], antioxidant [3], anticancer [4– 6], anti-in�ammatory [7], and antimicrobial agents [8] like unsubstituted �avonoids. Recently antitubercular chromones and �avonoids [9] having methyl substitution were isolated from Pisonia aculeate, which belongs to Nyctaginaceae fam- ily. Among these the titled compound pisonivanone was reported as a potent antituberculosis compound (MIC = 12.5 g/mL). So in order to develop the activity pro�le of the methyl substituted �avonoids, an attempt was made to synthesi�e pisonivanone for the �rst time and other new chalcones and �avanones. ese synthesi�ed compounds were screened for some biological activities like antioxidant, cytotoxic, and antituberculosis. e scheme for the synthesis of Pisonivanone and other analogs was given below (Scheme 1). 2-Hydroxy-3-methyl-4,6-dimethoxy acetophenone (1) was synthesised in different ways [10]. In the present work, we aimed to synthesise the key intermediate acetophenone (1) from phloroglucinol using regular conventional methods like methylation [11], formylation [12], Wolf-Kishner reduc- tion, and acetylation [12] with better yields (Scheme 2). All the intermediates were con�rmed by comparing the spectral data and melting points with the literature. Chalcones are versatile molecules and intermediates for synthesis of different heterocyclic compounds [13]. Chal- cones have been synthesised in different ways [14, 15]. e chalcones (3a–h) were synthesised by Claisen-Schmidt reaction. In this reaction, condensation was between ace- tophenone (1) and substituted aromatic aldehydes (2a–h) in the presence of aqueous KOH and ethanol at room temperature. Flavanones (Compound 4a–h) were prepared on cyclisa- tion of chalcones (Compounds 3a–h, resp.) in the presence of alcoholic H 2 SO 4 . Initially, chalcones were dissolved in alcoholic H 2 SO 4 and re�uxed at 60 ○ C for 24 hrs. Aer cooling, alcohol was removed under vacuum. When ice cold water added to the reaction, mass pale reddish colour solids were separated. ese solids were extracted with ethyl acetate. is ethyl acetate layer dried over sodium sulphate. is ethyl