Pyrrole antibiotic

Prodigiosin (Streptorubin B) (192) Tri-pyrrole antibiotic Obatoclax (GX15-070)(193) Oncology Bcl-2 inhibition Phase I/n Gemin X 911,912... 

Funabashi Y, Takizawa M, Tsubotani S, Tanida S, Harada S, Kamiya K (1992) Chemistry and Biological Activities of New Pyrrole Antibiotics, TAN-876A and B. J Takeda Res Lab 51 73... 

Consideration to the interesting group of pyrrole antibiotics obtained from Pseudomonas aeruginosa is not given in this Report, but is given elsewhere.5... 

Distamycins. Pyrrole antibiotics from Streptomyces distallicus, used topically to treat herpes simplex infections, e.g., D.A (stallimycin) C22H27N,04, Mr 481.51, mp. 154-156 °C used as the hydrochloride... 

C11H7CI2NO3, Mr 272.09 orange needles, mp. 174-175 (2 (decomp.). A pyrrole antibiotic from Pseudomonasfluorescens and the n-alkane-utilizing P. aeruginosa. P. possesses antibacterial, antifungal (e. g., against Pythium ultimum on cotton), and herbicidal activities. The biosynthesis proceeds from proline through the polyketide pathway. 

Pyrrole antibiotic. Prod, by Streptomyces sp. A18591. Antitumour agent. Similar to Prodigiosin, P-01862. 257 (28400), 325 (10000), 406 (8500) (MeOH). 

Pyrrole antibiotic. Isol. from the culture broth of... 

Kaneda, M., S. Akamura, N. Ezaki, and Y. litaka. 1981. Structure of pyrrolomycin B, a chlorinated nitro-pyrrole antibiotic. J Antibiot 34 (10) 1366-1368. 

ANTIBIOTICS - NUCLEOSIDES AND NUCLEOTIDES] (Vol 3) 5-(2H-Pyrrol-2-ylidenemethyl)-2,2y-bipyrrole [22187-69-5]... 

Table 1 Hsts the polyether antibiotics arranged by the number of carbons in the skeleton. Many of these compounds were isolated independendy in separate laboratories and thus have more than one designation. The groups are subdivided depending on the number of spiroketals. Two classes fall outside this scheme the pyrrole ether type containing a heterocycHc ring, and the acyltetronic acid type, that has an acyHdene tetronic acid instead of a carboxyHc acid. These compounds are ionophores and because of their common features are included as polyethers.

Aminoglycoside antibiotics and / -substituted indoles are stained red. Pyrrole derivatives with free / -positions react at room temperature to yield blue-colored zones [11]. Exposure to the vapors of aqua regia deepens the colors. This reaction sometimes produces fluorescence [3]. The detection limit for monomethylhydrazine is 200 pg per chromatogram zone [3]. 

Total syntheses of pyrrole alkaloids, furanoterpenes, macrolide antibiotics, and carbohydrates based on transformations catalyzed by transition metals 99SL1523. 

There are large numbers of naturally occurring representatives, especially of pyrrole that include the important polypyrroles (porphyrins and corrins), and the nitropyrrole antibiotics such as pyr-rolomycins and pyrroxamycin. Derivatives of furan have been used as fungicides and A-vinylpyr-rolidone is an important monomer for the production of blood plasma extenders and for cosmetic applications. On account of the similarity in the pathways for the aerobic degradation of monocyclic furan, thiophene, and pyrrole, all of them are considered here. Anaerobic degradation of furans is discussed in Part 2 of this chapter. 

Similar to the Pd-catalyzed pyrrole and thiophene annulations, an intramolecular Heck reaction of substrate 91 resulted in benzofuran 92 [80], Such an approach has become a popular means of synthesizing fused furans. Muratake et al. exploited the intramolecular Heck cyclization to establish the tricyclic core structure en route to the synthesis of a furan analog of duocarmycin SA, a potent cytotoxic antibiotic [81]. Under Jeffery s phase-transfer catalysis conditions, substrate 93 was converted to tricyclic derivatives 94 and 95 as an inseparable mixture (ca. 4 1) of two double bond isomers. 

Diethyl aminomalonate reacts with 1,3-diketones in boiling acetic acid to the corresponding pyrrolecarboxylates 11 (87JOC3986). From N-ac t-amidomalonate and acroleins, pyrrolidines were prepared and they were further transformed into functionalized pyrroles, which are a part of the antibiotic lyncomycin and an antimalarial agent (67JA2459 72JMC1255). 

Some total syntheses targeting structurally diverse and biologically active pyrrole alkaloids, fiiranoteipenes, macrolide antibiotics and carbohydrates have been suimnarized <99SL1S23>. 

Aromatic azapentalenes have not been found naturally, though an imidazo[4,5-d]imidazole derivative has been implicated in the prebiotic synthesis of purines130 74 (see also Section III,A,l,d). Saturated derivatives occur fairly widely the Senecio alkaloids contain the reduced pyrrolol l,2-a]pyrrole (pyrrolizidine) skeleton,487 and the alkaloid withasomnine is a derivative of pyrrolo[ l,2-6]pyrazole.374,488 The mitomycin antibiotics mentioned earlier in this review (Sections III,B,l,f and III,B,5) contain the pyrrolol l,2-a]indole ring,166,331 and the recently reported fungal metabolite sporidesmin is a saturated derivative of pyrrolo[2,3-6]indole.489... 

A synthesis of the marine antibiotic from Pseudomonas bromoutilis has been achieved by 1,3-dipolar cycloaddition of the oxazolone (388) with diethyl acetylenedicarboxylate (73CI(L)275). Hydrolysis and decarboxylation gave the pyrrole (390), identical with a sample prepared previously by other workers, and converted by them to pentabromopseudilin (391 Scheme 85) (66JA4509). 

Formamidine acetate (117) reacts with the pyrrole (118) in refluxing ethoxyethanol to give the pyrrolopyrimidine (119) which has been converted into the antibiotics toyocamycin, sangivamycin and tubercidin (Section 3.09.5) (69JA2102). A reaction with carbon disulfide... 

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