Sweet organic chemistry

Bragg, Rose Wilson; Chow, Yvonne; Dennis, Lawrence; Ferguson, Lloyd N.; Howell, S. Christopher; Morga, George; Ogino, C.; Pugh, H.; Winters, Manque

doi:10.1021/ed055p281

Cited by 12 publications

(5 citation statements)

References 17 publications

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“…The crude product was recrystallized from chloroform to give white crystals of hydrazide 5 (8.5 g, 85%, mp 71-72 °C). The analytical sample was prepared by further recrystallization from chloroform: mp 72.5-73.5 °C (lit.13 76-78 °C); MS, m/e 130 (M+); NMR (CDC13) 0.88 (m, 3, CH3), 2.2 (m, 2, CCH2), 4.0 (br s, 2, NH2), 8.0 (br s, 1, NH). Anal.…”

Section: -(6-carboxyhexyl)cyclopentanone Hexylhydrazone (3)mentioning

confidence: 99%

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2-(6-Carboxyhexyl)cyclopentanone hexylhydrazone. A potent and time-dependent inhibitor of platelet aggregation

Ghali¹,

Venton²,

Hung³

et al. 1983

J. Med. Chem.

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Two new azaprostanoids, a hydrazone (3) and hydrazide (4), have been prepared by the condensation of 2-(6-carboxyhexyl)cyclopentanone with n-hexylhydrazine and caproic acid hydrazide. Preliminary results with the stable hydrazide 4 indicate that it inhibits arachidonic acid (AA) induced human platelet aggregation and that, unlike 13-azaprostanoic acid (1), its site of action is at the cyclooxygenase level. Results with the unstable hydrazone derivative 3 indicate it to be a potent and time-dependent inhibitor of AA-induced human platelet aggregation, with its site of action also at the cyclooxygenase level.

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Section: -(6-carboxyhexyl)cyclopentanone Hexylhydrazone (3)mentioning

confidence: 99%

“…(1.3 g, 10 mmol) was heated to reflux for 20 min. While the solution cooled, feri-butyl n-hexylidenecarbazate (8) crystallized and was filtered (85%). Further concentration of the mother liquor separated the remainder of 8 (10%).…”

Section: -(6-carboxyhexyl)cyclopentanone Hexylhydrazone (3)mentioning

confidence: 99%

2-(6-Carboxyhexyl)cyclopentanone hexylhydrazone. A potent and time-dependent inhibitor of platelet aggregation

Ghali¹,

Venton²,

Hung³

et al. 1983

J. Med. Chem.

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“…The Sweet Taste Receptor In the case of the sense of taste, only salts are salty, only acids are sour, but a wide variety of structures are sweet, bitter, or tasteless. Most research in this area has been done on the sweet sense (11).…”

Section: XXmentioning

confidence: 99%

Bio-organic mechanisms: II. Chemoreception

Ferguson¹

1981

J. Chem. Educ.

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Guest molecules react with the normal biological constituents in at least six ways; (1) covalent bond formation, such as that done by the alkylating anticancer drugs and the carcinogenic aromatic hydrocarbons; (2) chelation If), the way in which dithiols interact in the treatment of heavy7 metal poisoning; (3) intercalation, the way proposed for certain cancer drugs such as adriamyein and the antibacterial acridine

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“…

Chemical Education many times before (1)(2)(3)(4)(5). Perhaps this is because sweeteners provide a link between chemical structure and biological activity to which everyone can easily relate.

…”

mentioning

confidence: 99%

Using Models to Understand and Design Sweeteners

Walters

1995

J. Chem. Educ.

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While most sweeteners have been discovered accidentally, many models have been devised to aid in understanding structure-taste relationships. Because of the diversity of structures which may exhibit sweet taste, it is difficult to devise a comprehensive model. In fact, it may not be appropriate to fit all sweeteners into a single model since multiple receptors may be involved. This paper describes the evolution of sweetness receptor models, culminating in computer-derived models which have successfully been used in the design of new sweeteners and in predicting how sweet new analogs will be.

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Sweet organic chemistry

Abstract: to examine some observed structure-taste correlations, and to explore one or two generalizations which might help elucidate the sNational Science Foundation Undergraduate Research Trainee.

Cited by 12 publications

References 17 publications

2-(6-Carboxyhexyl)cyclopentanone hexylhydrazone. A potent and time-dependent inhibitor of platelet aggregation

2-(6-Carboxyhexyl)cyclopentanone hexylhydrazone. A potent and time-dependent inhibitor of platelet aggregation

Bio-organic mechanisms: II. Chemoreception

Using Models to Understand and Design Sweeteners

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