Synthesis of penems and their antibacterial activities.

Oida, Sadao; Yoshida, Akira; Hayashi, Teruo; Takeda, Noriko; Nishimura, Tomonori; Ohki, Eiji

doi:10.7164/antibiotics.33.107

Cited by 9 publications

(2 citation statements)

References 4 publications

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“…Urinary recovery (24 h) of the drug is only 3%. Low urinary recovery in laboratory animals has been reported for other penems (OIDA et al 1980a). Sch 29482 is highly bound (>95%) by serum proteins and the addition of serum lowers its in vitro activity significantly .…”

Section: Penemsmentioning

confidence: 92%

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β-Lactam Antibiotics: Structure-Activity Relationships

Hoover¹

1983

Antibiotics

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Section: Penemsmentioning

confidence: 92%

“…While the MIC values of many of these penem analogs are better than those for penicillin V, they are not very different from the MIC values of ampicillin. However, the re- ERNST et al 1978;CHERRY et al 1979CHERRY et al , 1980BANVILLE et al 1981;OIDA et al 1980a. Values in parentheses, see text.…”

Section: Penemsmentioning

confidence: 99%

β-Lactam Antibiotics: Structure-Activity Relationships

Hoover¹

1983

Antibiotics

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Novel Synthetic Approaches to Monocyclic β‐Lactam Antibiotics

Hanessian

Sahoo

Couture

et al. 1984

Bulletin des Soc Chimique

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H X 3V1S u u r y : 6aubstituted amino acids is reported uith applications in the area of oonobactam antibiotics.Access to optically active 3-and 3.4-aubstituted aretidinones and to k a group of medicinally important compounds, feu if any have corsnded the interest of synthetic organic chemists as the 6-lactam antibiotics.1 fascinating molecules which spans close to half a century, la adorned uith remarkable achievements and milestone discoveries on several frontier areas of science. Nature continues to produce novel types of highly bioactive 6-lactam type antibiotics, thus challenging the laboratory scientist in m n y disciplines. In response, the microbiologist. the chemist and other experts in related fields have joined forces in their quest to conquer these structures. vith the discovery of innovative isolation techniques and ingeneous synthetic strategies. Figure 1 illustrates the structures of several generations of naturally-occurring 6-lactam antibiotics. The history of theseFigure 1 aivwic ACID w -c I N The penicillins and cephslosporins have been subjected to a relentless barrage of functional group and structural adificstion over the last several decades. Indeed. u c h novel chemistry h u emerged 6s s result of these s udies and the benefits to mankind have been enormous. With the discovery of thienamycin,' a ember of the carbapenem group of 6-lactam antibiotics, and an e t e m l y potent antibscterisl agent. an enormous potential for synthetic exploration emerged.'If Crest efforts have been M d e in chemical mdification in order to obtain more stable yet equally potent analogs. On a parallel front, ingeneous synthetic ochers have been devi ed which have culminated in a number of elegant syntheses of thienamycin and its analog^."^ Structurally-related, but stereochemic 11 different analogs have a 1 o been found in Nature as exemplified by the olivanic acidst : d the ssparenomycins. 9 R.U. Ratcliffe and C. Alkra-Schonkrg, in "Chemistry and Biology of 6-bctam Antibiotic#". R.M. Morin and M. -31 (1982); see also K. mano. Y. Kyotani. H. Ishiham, S. Kobagsshi and M. Ohno, J. Am. Chem. Soc.. 105. 7186-7187 (1983). I. Erneat, in "Chemistry and Biology of 6-bctam Antibiotics'. R.B. b r i n and M. G r M n . eds.Nature. 291, 489-491 (1981); see also A.I. Hada. K. Kitano. K. Kintaka, h r o i and M. k a i . Nature. 289, 590-591 (1981).

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The Penems, a New Class of β‐Lactam Antibiotics. 6. Synthesis of 2‐alkylthiopenem carboxylic acids

Lang

Prasad

Gosteli

et al. 1980

Helvetica Chimica Acta

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A synthesis of 2-alkylthiopenems by an intramolecular Wittig-type reaction between a phosphorane and a trithiocarbonate ester is described.In previous publications we described synthetic methods for the preparation of this new class of p-lactam antibiotics [l-41. The approaches involved routes starting from penicillin V or penicillanic acid [l] [2] and total syntheses [3] [4] from 4-acetoxyazetidin-2-one [5].The antibiotic potency and the wide spectrum of activity of the substances prepared so far warranted the search for the application of the methods to the synthesis of novel target structures. In view of the recent appearance of thienamycin [6] [7], epithienamycins [8] and PS-5 [9] we were particularly interested in combining common structural feature of these carbapenem antibiotics, an aliphatic side-chain attached in 2-position via a sulfur atom, with the penem nucleus.In the present paper we describe the assembly of this system. The key reaction involved the intramolecular Wittig-type reaction between a carbonyl-stabi-Table. Antibacterial in vitro Activities of the Penemcarboxylic Acids 8a ( R = C~H S ) and 8b (RE (CH&NHCOCH3) Microorganism 8a 8b

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Synthesis of penems and their antibacterial activities.

Cited by 9 publications

References 4 publications

β-Lactam Antibiotics: Structure-Activity Relationships

β-Lactam Antibiotics: Structure-Activity Relationships

Novel Synthetic Approaches to Monocyclic β‐Lactam Antibiotics

The Penems, a New Class of β‐Lactam Antibiotics. 6. Synthesis of 2‐alkylthiopenem carboxylic acids

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