“…Anal. (C12H1206) C, H. 2.5-Bis(hydroxymethyl)-l,4-benzoquinone Bis (hydrogen succinate) (9). To a solution of 27 (1.99 g, 5 mmol) in CH3CN (20 mL) was added, dropwise and with stirring, a solution of Ce(NH4)2(N03)6 (5.5 g, 10 mmol) in H20 (20 mL).…”
Section: Methodsmentioning
confidence: 99%
“…Mono and Bis(bioreductive) Alkylating Agents: Synthesis and Antitumor Activities in a B16 Melanoma Model Donald T. Witiak,* John T. Loper, Subramaniam Ananthan, Anna Maria Almerico, Vernon L. Verhoef, and Joyce A. Filppi Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, Ohio 43210, and Adria Laboratories, Division of Erbemont Inc., Columbus, Ohio 43216. Received July 22,1988 Several potentially bis (alkylating) bis(quinones) (3)(4)(5) and 1,4-and l,3-bis(alkylating) monoquinones (6)(7)(8)(9)(10)(11)(12)(13) belonging to general structure 2,2'-ethylenebis [5-[ (leaving group)methyl] -1,4-benzoquinone] (3-5) and 2,5-and 2,6-bis[ (leaving group)methyl]-1,4-benzoquinone water-soluble and -insoluble classes were prepared by oxidative demethylation of the corresponding tetramethoxydiphenylethanes (17)(18)(19) and dimethoxybenzenes (24,27,36-39), respectively. Methods employed for the preparation of tetramethoxydiphenylethane intermediates involved (1) arylmethyl bromide coupling and (2) catalytic hydrogenation of stilbene intermediates derived via Wittig reaction of (arylmethyl)phosphonium salts with aryl aldehydes.…”
Several potentially bis(alkylating) bis(quinones) (3-5) and 1,4- and 1,3-bis(alkylating) monoquinones (6-13) belonging to general structure 2,2'-ethylenebis[5-[(leaving group)methyl]-1,4-benzoquinone] (3-5) and 2,5- and 2,6-bis[(leaving group)methyl]-1,4-benzoquinone water-soluble and -insoluble classes were prepared by oxidative demethylation of the corresponding tetramethoxydiphenylethanes (17-19) and dimethoxybenzenes (24, 27, 36-39), respectively. Methods employed for the preparation of tetramethoxydiphenylethane intermediates involved (1) arylmethyl bromide coupling and (2) catalytic hydrogenation of stilbene intermediates derived via Wittig reaction of (arylmethyl)phosphonium salts with aryl aldehydes. However, in biological investigations using a subcutaneous B16 (hypoxic) melanoma tumor in BDF1 hybrid mice with cyclophosphamide as positive control the most interesting series of structurally related analogues were the potentially monoalkylating monoquinones of the 2-[(leaving group)methyl]-1,4-benzoquinone type (i.e., 14 and 15) having water-insoluble (acetoxy) and water-solubilizing (succinate) groups. Serial measurements of tumor size, and evaluation of increased life span, in response to drug treatment also revealed potentially 1,4-bis(alkylating) (bromomethyl)-1,4-quinone 7 and 1,3-bis(alkylating) (hydroxymethyl)-1,4-quinone 10 to have variable activity, but none of the potentially bis(alkylating) bis(quinones) showed antitumor properties in this model.
“…Anal. (C12H1206) C, H. 2.5-Bis(hydroxymethyl)-l,4-benzoquinone Bis (hydrogen succinate) (9). To a solution of 27 (1.99 g, 5 mmol) in CH3CN (20 mL) was added, dropwise and with stirring, a solution of Ce(NH4)2(N03)6 (5.5 g, 10 mmol) in H20 (20 mL).…”
Section: Methodsmentioning
confidence: 99%
“…Mono and Bis(bioreductive) Alkylating Agents: Synthesis and Antitumor Activities in a B16 Melanoma Model Donald T. Witiak,* John T. Loper, Subramaniam Ananthan, Anna Maria Almerico, Vernon L. Verhoef, and Joyce A. Filppi Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, Ohio 43210, and Adria Laboratories, Division of Erbemont Inc., Columbus, Ohio 43216. Received July 22,1988 Several potentially bis (alkylating) bis(quinones) (3)(4)(5) and 1,4-and l,3-bis(alkylating) monoquinones (6)(7)(8)(9)(10)(11)(12)(13) belonging to general structure 2,2'-ethylenebis [5-[ (leaving group)methyl] -1,4-benzoquinone] (3-5) and 2,5-and 2,6-bis[ (leaving group)methyl]-1,4-benzoquinone water-soluble and -insoluble classes were prepared by oxidative demethylation of the corresponding tetramethoxydiphenylethanes (17)(18)(19) and dimethoxybenzenes (24,27,36-39), respectively. Methods employed for the preparation of tetramethoxydiphenylethane intermediates involved (1) arylmethyl bromide coupling and (2) catalytic hydrogenation of stilbene intermediates derived via Wittig reaction of (arylmethyl)phosphonium salts with aryl aldehydes.…”
Several potentially bis(alkylating) bis(quinones) (3-5) and 1,4- and 1,3-bis(alkylating) monoquinones (6-13) belonging to general structure 2,2'-ethylenebis[5-[(leaving group)methyl]-1,4-benzoquinone] (3-5) and 2,5- and 2,6-bis[(leaving group)methyl]-1,4-benzoquinone water-soluble and -insoluble classes were prepared by oxidative demethylation of the corresponding tetramethoxydiphenylethanes (17-19) and dimethoxybenzenes (24, 27, 36-39), respectively. Methods employed for the preparation of tetramethoxydiphenylethane intermediates involved (1) arylmethyl bromide coupling and (2) catalytic hydrogenation of stilbene intermediates derived via Wittig reaction of (arylmethyl)phosphonium salts with aryl aldehydes. However, in biological investigations using a subcutaneous B16 (hypoxic) melanoma tumor in BDF1 hybrid mice with cyclophosphamide as positive control the most interesting series of structurally related analogues were the potentially monoalkylating monoquinones of the 2-[(leaving group)methyl]-1,4-benzoquinone type (i.e., 14 and 15) having water-insoluble (acetoxy) and water-solubilizing (succinate) groups. Serial measurements of tumor size, and evaluation of increased life span, in response to drug treatment also revealed potentially 1,4-bis(alkylating) (bromomethyl)-1,4-quinone 7 and 1,3-bis(alkylating) (hydroxymethyl)-1,4-quinone 10 to have variable activity, but none of the potentially bis(alkylating) bis(quinones) showed antitumor properties in this model.
“…Such an effect influences the reactivity of the quinone. Wegner et al (23) have shown that the greater the inductive effect of the benzylic substituent the easier the quinone is to reduce. Once the quinone is reduced the corresponding hydroquinone is harder to oxidize.…”
A series of hypericin analogs were found to differ in their cytotoxic activity induced by ambient light levels. These analogs vary in their ability to partition into cells, to generate singlet oxygen as well as in other photophysical properties. The data suggest that the biological activity of hypericin is due to a combination of factors whose roles may vary under different circumstances.
“…The quinone 5 that carries a propionic acid side chain was prepared by oxidation of 3-(2-hydroxyphenyl)propionic acid ( 4 ) with bis(trifluoroacetoxy)iodobenzene in an acetonitrile/water mixture. This route is much shorter than the published one. , 1 Synthesis of the Substituted Quinones 2 a , 2b , and 5 …”
Several Diels-Alder adducts between benzoquinones and cyclopentadiene were reduced to the corresponding diols 7a-c and 11. Treatment of these diols with strong acid triggered a skeletal rearrangement reaction resulting in compounds 8a-c and 12 that contain a 4,8-methanoazulene substructure. In addition, a dyotropic-like rearrangement of the tetracyclic lactone 13 to the spiro-lactone 18 was observed. Five of the structures were supported by X-ray analysis.
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