Catalysis by molecular iodine: A rapid synthesis of 1,8-dioxo- octahydroxanthenes and their evaluation as potential anticancer agents

Naveen Mulakayala; P. V.N.S. Murthy; D. Rambabu; Madhu Aeluri; Raju Adepu; G. R. Krishna; C. Malla Reddy; K. R.S. Prasad; M. Chaitanya; Chitta S. Kumar; M. V. Basaveswara Rao; Manojit Pal

doi:10.1016/j.bmcl.2012.01.126

Catalysis by molecular iodine: A rapid synthesis of 1,8-dioxo- octahydroxanthenes and their evaluation as potential anticancer agents

Naveen Mulakayala, P. V.N.S. Murthy, D. Rambabu, Madhu Aeluri, Raju Adepu, G. R. Krishna, C. Malla Reddy, K. R.S. Prasad, M. Chaitanya, Chitta S. Kumar, M. V. Basaveswara Rao, Manojit Pal

Research output: Contribution to journal › Article › peer-review

118 Scopus citations

Abstract

Molecular iodine facilitated the reaction of 5,5-dimethyl-1,3- cyclohexanedione with aromatic aldehydes in iso-propanol affording a variety of 1,8-dioxo-octahydroxanthenes in high yields. Most of the compounds synthesized showed good anti-proliferative properties in vitro against three cancer cell lines and 9-(2-hydroxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H- xanthene-1,8(2H)-dione possessing a 2-hydroxy phenyl group at C-9 position was found to be promising. Further structure elaboration of the same compound and the crystal structure analysis and hydrogen bonding patterns of another compound that is, 9-(4-methoxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H- xanthene-1,8(2H)-dione prepared by using this methodology is presented.

Original language	English
Pages (from-to)	2186-2191
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	22
Issue number	6
DOIs	https://doi.org/10.1016/j.bmcl.2012.01.126
State	Published - 15 Mar 2012
Externally published	Yes

Keywords

1,8-Dioxo-octahydroxanthene
5,5-Dimethyl-1,3-cyclohexanedione
Iodine

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.1016/j.bmcl.2012.01.126

Cite this

Mulakayala, N., Murthy, P. V. N. S., Rambabu, D., Aeluri, M., Adepu, R., Krishna, G. R., Reddy, C. M., Prasad, K. R. S., Chaitanya, M., Kumar, C. S., Basaveswara Rao, M. V., & Pal, M. (2012). Catalysis by molecular iodine: A rapid synthesis of 1,8-dioxo- octahydroxanthenes and their evaluation as potential anticancer agents. Bioorganic and Medicinal Chemistry Letters, 22(6), 2186-2191. https://doi.org/10.1016/j.bmcl.2012.01.126

@article{a3bd4ef5c0ca48eb9b1bb56acac27f34,

title = "Catalysis by molecular iodine: A rapid synthesis of 1,8-dioxo- octahydroxanthenes and their evaluation as potential anticancer agents",

abstract = "Molecular iodine facilitated the reaction of 5,5-dimethyl-1,3- cyclohexanedione with aromatic aldehydes in iso-propanol affording a variety of 1,8-dioxo-octahydroxanthenes in high yields. Most of the compounds synthesized showed good anti-proliferative properties in vitro against three cancer cell lines and 9-(2-hydroxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H- xanthene-1,8(2H)-dione possessing a 2-hydroxy phenyl group at C-9 position was found to be promising. Further structure elaboration of the same compound and the crystal structure analysis and hydrogen bonding patterns of another compound that is, 9-(4-methoxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H- xanthene-1,8(2H)-dione prepared by using this methodology is presented.",

keywords = "1,8-Dioxo-octahydroxanthene, 5,5-Dimethyl-1,3-cyclohexanedione, Iodine",

author = "Naveen Mulakayala and Murthy, {P. V.N.S.} and D. Rambabu and Madhu Aeluri and Raju Adepu and Krishna, {G. R.} and Reddy, {C. Malla} and Prasad, {K. R.S.} and M. Chaitanya and Kumar, {Chitta S.} and {Basaveswara Rao}, {M. V.} and Manojit Pal",

year = "2012",

month = mar,

day = "15",

doi = "10.1016/j.bmcl.2012.01.126",

language = "English",

volume = "22",

pages = "2186--2191",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Ltd.",

number = "6",

}

Mulakayala, N, Murthy, PVNS, Rambabu, D, Aeluri, M, Adepu, R, Krishna, GR, Reddy, CM, Prasad, KRS, Chaitanya, M, Kumar, CS, Basaveswara Rao, MV & Pal, M 2012, 'Catalysis by molecular iodine: A rapid synthesis of 1,8-dioxo- octahydroxanthenes and their evaluation as potential anticancer agents', Bioorganic and Medicinal Chemistry Letters, vol. 22, no. 6, pp. 2186-2191. https://doi.org/10.1016/j.bmcl.2012.01.126

TY - JOUR

T1 - Catalysis by molecular iodine

T2 - A rapid synthesis of 1,8-dioxo- octahydroxanthenes and their evaluation as potential anticancer agents

AU - Mulakayala, Naveen

AU - Murthy, P. V.N.S.

AU - Rambabu, D.

AU - Aeluri, Madhu

AU - Adepu, Raju

AU - Krishna, G. R.

AU - Reddy, C. Malla

AU - Prasad, K. R.S.

AU - Chaitanya, M.

AU - Kumar, Chitta S.

AU - Basaveswara Rao, M. V.

AU - Pal, Manojit

PY - 2012/3/15

Y1 - 2012/3/15

N2 - Molecular iodine facilitated the reaction of 5,5-dimethyl-1,3- cyclohexanedione with aromatic aldehydes in iso-propanol affording a variety of 1,8-dioxo-octahydroxanthenes in high yields. Most of the compounds synthesized showed good anti-proliferative properties in vitro against three cancer cell lines and 9-(2-hydroxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H- xanthene-1,8(2H)-dione possessing a 2-hydroxy phenyl group at C-9 position was found to be promising. Further structure elaboration of the same compound and the crystal structure analysis and hydrogen bonding patterns of another compound that is, 9-(4-methoxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H- xanthene-1,8(2H)-dione prepared by using this methodology is presented.

AB - Molecular iodine facilitated the reaction of 5,5-dimethyl-1,3- cyclohexanedione with aromatic aldehydes in iso-propanol affording a variety of 1,8-dioxo-octahydroxanthenes in high yields. Most of the compounds synthesized showed good anti-proliferative properties in vitro against three cancer cell lines and 9-(2-hydroxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H- xanthene-1,8(2H)-dione possessing a 2-hydroxy phenyl group at C-9 position was found to be promising. Further structure elaboration of the same compound and the crystal structure analysis and hydrogen bonding patterns of another compound that is, 9-(4-methoxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H- xanthene-1,8(2H)-dione prepared by using this methodology is presented.

KW - 1,8-Dioxo-octahydroxanthene

KW - 5,5-Dimethyl-1,3-cyclohexanedione

KW - Iodine

UR - http://www.scopus.com/inward/record.url?scp=84857912298&partnerID=8YFLogxK

U2 - 10.1016/j.bmcl.2012.01.126

DO - 10.1016/j.bmcl.2012.01.126

M3 - Article

C2 - 22365759

AN - SCOPUS:84857912298

SN - 0960-894X

VL - 22

SP - 2186

EP - 2191

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 6

ER -

Catalysis by molecular iodine: A rapid synthesis of 1,8-dioxo- octahydroxanthenes and their evaluation as potential anticancer agents

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

Access to Document

Other files and links

Fingerprint

Cite this