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42 Chemistry and Biology of Beta-Lactams
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FIGURE 1.55 Tricyclic beta-lactam.
FIGURE 1.56 4-Methoxy-tribactam.
Gram-negative ones. The stability of sanfetrinem against a wide range of beta-lactamases has been
demonstrated to be high. The activity of sanfetrinem, formerly GV104326, was determined by using
a broth microdilution MIC method versus a large number of clinical isolates from S. pneumoniae, H.
inuenzae, and M. catarrhalis obtained during a recent surveillance study of 30 centers throughout the
United States. For these three groups of bacteria, sanfetrinem MIC50 and MIC90 values were found to
be 0.015 and 0.5 g/mL, 0.25 and 0.5 g/mL, and 0.015 and 0.03 g/mL, respectively.
164
Tricyclic carbapenems (trinems) have been synthesized with a pyrrolidinyl moiety at the C4 position of
the tricyclic ring in order to study their antimicrobial activities.
165
There was evidence that these trinems
were effective against Gram-positive bacteria, including methicillin-resistant S. aureus (MRSA). Among
these compounds, the (4R)- [(S)- pyrro lidin -3-yl thiom ethyl ]trin em exhibited good activity against MRSA
both in vitro and in vivo.
The total synthesis of the tricyclic beta-lactams, “5α- and 5β-methoxy tribactams”, positional isomers
of the Glaxo 4α-methoxy-tribactam is described, and preliminary biological evaluation is reported.
166
A
schematic representation of the synthesis is shown in Fig ure 1.57 and Figure 1.58.
An overview of preliminary data on the antibacterial activity of 21 and 24 is presented in Ta ble 1.5. In
contrast to the B-epimer 24, the activity of the a-methoxyisomer 21 is comparable to that of imipenem in
most bacteria, with the exception of P. aeruginosa and some anaerobes.
Several studies have been carried out to investigate the synthesis and biological activity of 4-ureido
trinems 1 obtained by the condensation of various isocyanates with the intermediate 6. It was demonstrated that 4-N-methyI-N’-alkyl ureido trinems showed a promising antimicrobial activity against
Gram-negative bacteria, among others.
167
As a result, the advanced intermediate 6 was easily converted
into this class of molecules by reacting with various commercial or synthetic isocyanates (Fig ure 1.59).
Total synthesis is shown in Figure 1.60.
According to preliminary results that have been obtained with 4-N-methyl-N’-alkyl ureido trinems 1
a-d, these compounds have shown to have good antibacterial activity across a wide range of representative bacteria that have been studied (Table 1.6). Compounds lb and le showed moderate permeability
problems against Gram-negative strains as evidenced by the fact that their activities differed from those
of the wild-type E. coli 1850 and the permeable strain E. coli 1919. It has been observed that all of the
compounds have demonstrated stability to beta-lactamase enzymes, as shown by the observed activity
against beta-lactamase-producing strains, and stability to DHP-I enzymes.
In order to increase the antimicrobial activity of trinem, the methoxy group has been introduced at the
allylic C4 position, which has resulted in a dramatic increase in its antimicrobial activity. There has been
an attempt to introduce an oxygen atom alternatively at the allylic positions 5 and 7 of trinem in order
43Beta-Lactams
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FIGURE 1.57 Synthesis of tricyclic beta-lactam 21: (a) i. NaH (2.5 eq), 0°C, THF; ii. add compound 4 −78°C to 0°C, 2
hours; (b) TBDMSOTf, 2,6-1-utidine, 0°C, CH2C12, 30 minutes, 84%; (c) Pd(OAc)2 (l mol%) , Ph3P, (5mo1%), formic acid (3
eq), reux, EtOAc, 2.5 hours, 80%; (d) HOAc (2 eq), TBAF (1 eq), rt, THF, 30 minutes, 98%; (e) i. DiBAIH, −78°C, THF,
1.5 hours; ii. aqueous workup with 10% HCI, 80%; (f) i. NaHMDS (1 eq), −78°C, THF; ii. benzyl 2-bromoacetate (1.2 eq),
−78°C, 30 minutes, 72%; (g) i. NaHMDS (1.1 eq), −78°C, THF; ii. ZnCI2, −78°C, 30 minutes; iii. PhSeBr (1.1 eq), −78°C,
15 minutes, 70%; (h) mCPBA (2 eq), −78°C, CH2C12, 30 minutes, 80%; (i) NaBH4 (1.1 eq), −78°C, MeOH, 30 minutes,
75%; ( j) MeI (solvent), Ag2O (3 eq), rt, 10 hours, 63%; (k) DBU (1 eq), rt, CH2C12, 12 hours, 92%; (1) TBAF (3 eq), HOAc
(4 eq), rt, THF, 4 days, 85%; (m) 3,3,6 ,9,9- penta methy l-2,1 0-dia zabic yclo[ 4.4.0 ]dec- l-ene , H2, Pd(C), rt, dioxane, l hour,
93%. Adapted with permission from Hanessian S et al. (1995).
to achieve the antibacterial activity. Specically, compounds 3 and 4 have been demonstrated to be of
signicant interest in terms of their antibacterial activity.
A series of tricyclic beta-lactams were synthesized and evaluated for in vitro antibacterial activities against carbapenem-resistant Enterobacterales (CREs).
lactam, which was combined with a cephalosporin skeleton with a game-lactone ring and a carboxylic
168
As a result of a report of a tricyclic beta-
44 Chemistry and Biology of Beta-Lactams
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FIGURE 1.58 Synthesis of 5b-methoxy-tribactam 24: (a) i. H2, Pd(C)(cat.), EtOAc, 2 hours; ii. benzyl oxalylchloride,
pyridine, CH2C12, 0°C to rt, 2 hours; iii. P(OEt)3, xylene, 155°C, overnight, iv, chromatography, IS-isomer 24%, total
48%; (b) TBAF (3 eq), HOAc (4 eq), rt, THF, 4 days, 83%; (c) 3,3,6 ,9,9- penta methy l-2,1 0-dia zabic yclo[ 4.4.0 ]dec- l-ene , H2,
Pd(C), rt, dioxane, 1 hour, 100%. Adapted with permission from Hanessian S et al. (1995).
TABLE 1. 5
Antibacterial Activity of 21 and 24
Organism
S. aureus 663E
S. aureus 853E
S. aureus 1131
S. aureus COL
E. faecalis 850 4
H. inuenzae 49247 0.5 16 1
E. coli DC
E. coli DC
E. coli DC2 TEM1g 1 1 0.5
E. cloacae 3647 1 16 2
P. mirabilis 355g 4 32 1
P. aeruginosa 1911E
P. aeruginosa 2032E WT
P. aeruginosa 2033E
C. perfringens 615E 0.5 8 0.06
B. fragilis 2017E 1 32 0.13
a
b
c
d
e
f
g
h
Source: Adapted with permission from Hanessian S et al. (1995).
a
b
c
d
d
e
0
f
2
h
21 24 Imipenem
0.25 1 0.13
0.5 1 0.13
32
>32
4
>32 >32 >32
>32
1
1 16 0.5
1 0.5 0.5
>32 >32
>32 >32
4
4
1 16 0.5
MIC values were determined by conventional dilution techniques in microtiter broth using the procedures as laid down by NCCLS and are dened as the
lowest concentration (µg/mL) giving no visible growth after 16–20 hours.
Pen, sens.;
b-lactamase prod. strain;
methicillin resist.;
wild;
permeable;
permeable, b-lactamase prod. strain;
permeable mutant.
acid group, which was identied as a unique partial structure of Lactivicin, a compound which has
shown potent antibacterial activity against all tested CREs has been identied by adding sulfoxide. The
sulfoxide-introduced tricyclic beta-lactam also showed strong therapeutic efcacy in the neutropenic
mouse lung infection model. Taking into account the results of this study, it can be concluded that the
FIGURE 1.59 4-Ureido trinems. Adapted with permission from Géhanne S et al. (1996).
https://t.me/med1917
45Beta-Lactams
FIGURE 1.60 Synthesis of 4-ureido trinem: i) DIPEA, BnCO2CI, CH2CI2; ii) (COC1)2, DMSO, Et3N. CH2C12, −60°C;
iii) K2CO3, Py, ClCOCO2Bn; iv) P(OEt)3, xylene, 120°C; v) TBAF, CH3COOH, THF, rt; vi) 10% Pd/C, H2, iPrOH, H2O,
NaHCO3; vii) RNCO, H2O. Adapted with permission from Géhanne S et al. (1996).
TABLE 1.6
Antibacterial Activity
1a
1b 0.25
1c 0.50
1d 0.25
Sanfetrinem 0.25
Imipenem 0.10
Source: Adapted with permission from Géhanne S et al. (1996).
S. aureus
853
≤0.12 ≤0.12
S. pneumoniae
3512
≤0.12
≤0.12
≤0.12
≤0.01
≤0.01
E. coli
1850 W T
0.25
2.00 0.25
4.00 0.50
0.50
0.50 0.50 0.03 0.06 16
0.50 0.50 0.03 0.06 4 4
E. coli
1919 PM
≤0.12 ≤0.12 ≤0.12
≤0.12 ≤0.12
C. perfringens
615
≤0.12
≤0.12
B. fragilis
2017
0.50 4 16
0.50 2 16
0.25 8 16
P. aer ugi nos a
2032 WT
1 8
P. aer ugi nos a
1911
>32
46 Chemistry and Biology of Beta-Lactams
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FIGURE 1.61 Tetracyclic dibenzo[b,f][1,4]oxazepine-fused β-lactams.
FIGURE 1.62 Tetracyclic beta-lactams.
tricyclic beta-lactam skeleton is likely to show sufcient therapeutic performance in clinical use and can
therefore be used as a scaffold in the search for new antibacterial agents against CREs.
An efcient process for the stereoselective synthesis of tricyclic beta-lactams from a readily available cephalosporin intermediate using sulfoxide-directed oxidative lactonization was reported.
169
Tricyclic beta-lactam antibiotics also show signicant antibacterial activity against carbapenem-resistant
Enterobacterales (CREs). In normal cases, in order to synthesize a key intermediate for tricyclic betalactam antibiotics, eight steps must be taken from penicillin, with a low yield of about 3% via the formation of non-stereoselective lactones. However, by utilizing a sulfoxide-directed oxidative lactonization
process from an inexpensive commercially available intermediate of cephalosporins, it was able to synthesize a stereoselective tricyclic beta-lactam ring in a complete yield of 23% in six steps.
1.5 Tetracyclic β-Lactams
It should be noted that there has also been research carried out on the tetracyclic beta-lactam. It was
recently reported that the tetracyclic dibenzo[b,f][1,4]oxazepine-fused beta-lactams (Fig u r e 1.61)
were synthesized via visible light-induced Staudinger annulations.
Staudinger [2+2] annulation reaction between α-diazo ketones and diben zo[b, f][1, 4]oxa zepin e/thi azepi
ne-im ines under catalyst-free conditions has been developed. This protocol provides a facile method to
synthesize tetracyclic diben zo[b, f][1, 4]oxa zepan e/thi azepi ne-fu sed beta-lactams bearing a quaternary
carbon center with a broad substrate scope and high efciency (37 examples, up to >99% yield).
The synthesis of polycyclic beta-lactams (Figure 1.62) from d-glucose-derived chiral templates via
substrate-controlled radical cyclization was described.
171
In the cyclization process, the radical acceptor
allyl group is at N-1, and the radical progenitor is on a sugar moiety, which is anchored to the beta-lactam
ring at C4, where radical cyclization proceeds via 6-exo and 7-endo heptenyl radical cyclization. During
the radical cyclization of N-propargyl substrates, the mode of radical cyclization is highly stereospecic
and is controlled by the stereochemistry of the beta-lactam ring.
170
An efcient visible light-induced
47Beta-Lactams
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1.6 Conclusion
In this chapter, we have discussed the biogenesis, physical characteristics, and medicinal activities of
different beta-lactams. Basically, we considered the monocyclic β-lactams, bicyclic β-lactams, tricyclic
β-lactams, and tetracyclic β-lactams.
Acknowledgments
AD is grateful to CEA-Grenoble, Joseph Fourier University, University of Göttingen, University of
California, Los Angeles, for their support. BKB is grateful to the US NIH, the US NCI, Texas Kleberg
Foundation, Stevens Institute of Technology, University of Texas MD Anderson Cancer Center, University
of Texas-Pan American, and Community Health Systems of Texas for their nancial and moral support
to his research. AD and BKB are also grateful to their current employer, Prince Mohammad Bin Fahd
Un iversit y.
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compounds. In: Das A, Banik B, eds. Microwaves in Chemistry Applications. Advances in Green and
Sustainable Chemistry. Elsevier; 2021:107–142. doi:10.1016/ B978-0-12-822895 -1.0 0 010 -2
52. Das A, Banik BK. Chapter 5 – Microwave-assisted synthesis of N-heterocycles. In: Das A, Banik B,
eds. Microwaves in Chemistry Applications. Advances in Green and Sustainable Chemistry. Elsevier;
2021:143 –198. doi:10.1016/B978-0-12-822895-1.00006-0
53. Das A, Banik BK. Chapter 6 – Microwave-assisted oxidation and reduction reactions. In: Das A, Banik
B, eds. Microwaves in Chemistry Applications. Advances in Green and Sustainable Chemistry. Elsevier;
2021:199–244. doi:10.1016/B978-0-12-822895-1.00001-1
54. Das A, Banik BK. Chapter 7 – Microwave-assisted enzymatic reactions. In: Das A, Banik B, eds.
Microwaves in Chemistry Applications. Advances in Green and Sustainable Chemistry. Elsevier;
2021:245–281. doi:10.1016/B978-0-12-822895-1.00009-6
55. Das A, Banik BK. Chapter 8 – Microwave-assisted sterilization. In: Das A, Banik B, eds. Microwaves
in Chemistry Applications. Advances in Green and Sustainable Chemistry. Elsevier; 2021:285–328.
doi:10.1016/B978-0-12- 822895 -1.0 0 011-4
56. Das A, Banik BK. Chapter 9 – Microwave-assisted CVD processes for diamond synthesis. In: Das A,
Banik B, eds. Microwaves in Chemistry Applications. Advances in Green and Sustainable Chemistry.
Elsevier; 2021:329–374. doi:10.1016/B978-0-12-822895-1.00004-7
57. Das A, Banik BK. Chapter 10 – Future trends in microwave chemistry and biology. In: Das A, Banik B,
eds. Microwaves in Chemistry Applications. Advances in Green and Sustainable Chemistry. Elsevier;
2021:375–384. doi:10.1016/B978-0-12-822895-1.00003-5
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of aromatic compounds: Effects of penetration depth. Asian J Chem. 2021;33:2203–2206. doi:10.14233/
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62. Das A, Banik BK. Semiconductor characteristics of tellurium and its implementations. Phys Sci Rev.
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Published online June 2, 2022. doi:10.1515/psr-2021- 0221
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