<b>The Total and Partial General Syntheses of the Penicillins</b>

Sheehan, John C.; Henery-Logan, Kenneth R.

doi:10.1021/ja00874a029

Cited by 78 publications

(11 citation statements)

References 2 publications

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“…As stated above, such a dissociation cannot be a mere reversal of reaction A2 (Fig. I), as the cyclization of a penicilloate to a penicillin requires highly unusual chemical conditions (Sheehan & Henery-Logan, 1962) ; the only possible route for PSC-P to dissociate seems to be that represented by reaction A3 which is the chemical notation for…”

mentioning

confidence: 99%

Bacterial resistance to penicillins and cephalosporins

Smith

Hamilton‐Miller

Knox

1969

Journal of Pharmacy and Pharmacology

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mentioning

confidence: 99%

Bacterial resistance to penicillins and cephalosporins

Smith

Hamilton‐Miller

Knox

1969

Journal of Pharmacy and Pharmacology

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“…Hetacillin (I) is not a true penicillin (II), in that the nitrogen on C6 is tertiary. A compound analogous in this respect is phthalimidopenicillin (III), which is devoid of biological activity [9]. It may be, therefore, that the presence of a hydrogen atom on the C6 nitrogen is essential for the anti bacterial action of a penicillin.…”

Section: Discussionmentioning

confidence: 99%

Hetacillin: A Chemical and Biological Comparison with Ampicillin

Smith¹,

Hamilton‐Miller²

1970

Chemotherapy

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Hetacillin breaks down in aqueous solution to give ampicillin and acetone, both of which products have been identified chemically. The rate of breakdown is maximal between pH values 5 and 8, and is considerably slower under more acid conditions. The finding that hetacillin does not react with hydroxylamine at pH 7, taken in conjunction with other data presented, suggests that the antimicrobial activity of hetacillin may be low or even neglibible, and that it must be converted to ampicillin to show significant biological activity. In a small double cross-over trial, using 250 mg of hetacillin and ampicillin, no significant differences were observed either in peak blood levels or in the time for which useful levels were maintained. It is concluded that, while hetacillin is likely to be as effective an antibiotic as ampicillin, it is unlikely to be more effective, and thus that it does not represent a significant therapeutic advance.

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“…10). The reactions corresponding to strategic sites 2 [34], 5 [35], and 11 . Frequency distributions of USS and RSS in THEILHEIMER [36] have already been published, which are treated as RSS.…”

Section: 0777mentioning

confidence: 99%

Development of Evaluation Model for Strategic Sites in Synthetic Route Design System AIPHOS

Tanaka¹,

Kawai²,

Matsumoto³

et al. 2008

J. Comput. Aided Chem.

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An evaluation technique was developed to prioritize synthetic strategic sites (a set of bonds to make precursors by cut and connection) for the purpose of effective retro-synthesis in synthetic route design system, AIPHOS. In this paper, the relationship between the strategic sites proposed by AIPHOS and the reaction centers in reaction databases was discussed. The correlation has been analyzed by logistic regression analysis (LoRA) with molecular centrality, bond dissociation energy (BDE), and the number of bonds. We used the equation to clarify the importance of synthetic strategy sites. The correlation models showed high similarity among three reaction databases. In addition, from the model, reaction centers in reaction databases were found to be located in the center of the whole structures, to have fewer bonds, and to have smaller bond dissociation energies.

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The Total and Partial General Syntheses of the Penicillins

Cited by 78 publications

References 2 publications

Bacterial resistance to penicillins and cephalosporins

Bacterial resistance to penicillins and cephalosporins

Hetacillin: A Chemical and Biological Comparison with Ampicillin

Development of Evaluation Model for Strategic Sites in Synthetic Route Design System AIPHOS

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