1310697-89-2Relevant academic research and scientific papers
Facile synthesis of 1,2-dione-containing abietane analogues for the generation of human carboxylesterase inhibitors
Binder, Randall J.,Hatfield, M. Jason,Chi, Liying,Potter, Philip M.
supporting information, p. 79 - 89 (2018/03/06)
Recently, a series of selective human carboxylesterase inhibitors have been identified based upon the tanshinones, with biologically active molecules containing a 1,2-dione group as part of a naphthoquinone core. Unfortunately, the synthesis of such compounds is complex. Here we describe a novel method for the generation of 1,2-dione containing diterpenoids using a unified approach, by which boronic acids are joined to vinyl bromo-cyclohexene derivatives via Suzuki coupling, followed by electrocyclization and oxidation to the o-phenanthroquinones. This has allowed the construction of a panel of miltirone analogues containing an array of substituents (methyl, isopropyl, fluorine, methoxy) which have been used to develop preliminary SAR with the two human carboxylesterase isoforms. As a consequence, we have synthesized highly potent inhibitors of these enzymes (Ki 15 nM), that maintain the core tanshinone scaffold. Hence, we have developed a facile and reproducible method for the synthesis of abietane analogues that have resulted in a panel of miltirone derivatives that will be useful tool compounds to assess carboxylesterase biology.
1 -HYDROXY-BENZOOXABOROLES AS ANTIPARASITIC AGENTS
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Page/Page column 88, (2014/10/03)
Provided are compounds useful for controlling endoparasites both in animals and agriculture. Further provided are methods for controlling endoparasite infestations of an animal by administering an effective amount of a compound as described above, or a pharmaceutically acceptable salt thereof, to an animal, as well as formulations for controlling endoparasite infestations using the compounds described above or an acceptable salt thereof, and an acceptable carrier. The claimed compounds are described by the following Markush formula:A typical example for a compound according to above formula is: A typical example for a compound according to above formula is:
ANALGESIC COMPOUNDS, METHODS, AND FORMULATIONS
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Paragraph 0050, (2013/09/12)
Provided are analgesic compounds, and salts thereof, of formula: (I) wherein A is: (A) Additionally, pharmaceutical formulations and methods of use employing the above compounds are provided.
ANALGESIC COMPOUNDS, METHODS, AND FORMULATIONS
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Page/Page column 16, (2012/08/08)
Provided are compounds, and salts thereof, of formula (I): wherein (A) is R1 is hydrogen, C1-C5 alkyl, C1-C5 alkoxy, C1-C5 haloalkyl, C1-C5 alkanol, -(C1-C5 alkyl)phenyl, or phenyl, or a group of the formula -C(O)-R12, where R12 may be C1-C5 alkyl, C1-C5 alkoxy, C1-C5 haloalkyl, C1-C5 alkanol, -(C1-C5 alkyl)phenyl, or phenyl; R2 and R3 are independently hydrogen, C1-C5 alkyl, C1-C5 alkoxy, halogen, C1-C5 haloalkyl, or C1-C5 haloalkoxy; R4 and R5 are independently hydrogen, C1-C5 alkyl, or -(C1-C5 alkyl)phenyl; R6 is hydrogen, hydroxy, or is absent; R7 is hydrogen; R8 and R9 are independently hydrogen or methyl; R10 is hydrogen; R11 is hydrogen or C1-C5 alkyl; or R7 and R10 combine to form -CH2- or -(CH2)2-; or R8 and R9 combine to form a cyclopropyl group with the carbon to which they are attached; or R10 and R11 combine to form -CH2- or -(CH2)3-. Additionally, pharmaceutical formulations and methods of use employing the above compounds are provided.
ANALGESIC COMPOUNDS, METHODS, AND FORMULATIONS
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Page/Page column 16, (2012/08/08)
Provided are analgesic compounds, and salts thereof, of formula: ( I ) wherein A is: ( A ) Additionally, pharmaceutical formulations and methods of use employing the above compounds are provided.
Novel Compounds
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Page/Page column 66, (2011/06/24)
The present invention provides compounds of formula (I): wherein Ra, Rb, Rc, R1, R2, R3, X1, Y1, Z1, A, n and m are as defined in the specification, and pharmaceutically acceptable salts thereof, as well as processes for their preparation, pharmaceutical compositions containing them and their use in therapy.
