170238-94-5Relevant academic research and scientific papers
Cytotoxicity of substituted alkyl-3,4-bis(4-methoxyphenyl)pyrrole-2- carboxylates in L1210 lymphoid leukemia cells
Burnham,Gupton,Krumpe,Webb,Shuford,Bowers,Warren,Barnes,Hall
, p. 337 - 341 (1998)
Two alkyl-3,4-bis(4-methoxyphenyl)pyrrole-2-carboxylates proved to be potent cytotoxic agents in the murine L1210 lymphoid leukemia screen. DNA synthesis was preferentially inhibited with the major target of the agents being de novo purine biosynthesis at the regulatory enzyme sites of PRPP- amido transferase and IMP dehydrogenase. Other enzymatic activities which were suppressed by the drugs were DNA polymerase α, RNA polymerases, ribonucleoside reductase and dihydrofolate reductase. The d[NTP] pools, nucleoside kinase and the pyrimidine pathway were not affected by the presence of drugs. The DNA molecule itself was not the target of the agents, i.e. no alkylation of nucleotide bases, intercalation between bases or cross- linking of DNA strands occurred. The agents did cause L1210 DNA fragmentation after 24 h incubation at 100 μM.
Synthesis of lamellarin R, lukianol A, lamellarin O and their analogues
Liou, Teau-Jiuan,Satyanarayana, Iddum,Yang, Ding-Yah
, p. 43168 - 43174 (2020/12/18)
Three lamellarin alkaloids type III (lamellarin R, lukianol A and lamellarin O) were synthesized using the Barton-Zard reaction as a key step to construct the central pyrrole core. Some of their corresponding 4-benzoyl and 5-phenyl substituted pyrrole ana
Formation of 3,4-Diarylpyrrole- and Pyrrolocoumarin Core of Natural Marine Products via Barton–Zard Reaction and Selective O-Demethylation
Silyanova, Eugenia A.,Samet, Alexander V.,Salamandra, Lev K.,Khrustalev, Victor N.,Semenov, Victor V.
, p. 2093 - 2100 (2020/03/24)
A metal-free approach to 3,4-diarylpyrrole-2-carboxylate and pyrrolocoumarin cores of lamellarins and related natural products based on Barton–Zard reaction of nitrostilbenes with ethyl isocyanoacetate was developed. In the case of diarylpyrrole-2-carboxy
A Paal-Knorr approach to 3,4-diaryl-substituted pyrroles: Facile synthesis of lamellarins O and Q
Ramirez-Rodriguez, Armando,Mendez, Jose M.,Jimenez, Cristina C.,Leon, Fernando,Vazquez, Alfredo
, p. 3321 - 3326,6 (2012/12/12)
A very simple, yet efficient synthetic methodology, to obtain 3,4-diaryl-substituted pyrroles is described. The approach is based on the Knoevenagel condensation between arylacetonitriles and substituted aromatic aldehydes, followed by conjugate addition of cyanide to afford succinonitriles in excellent yields. The products thus obtained were subjected to DIBAL-H reduction, followed by cyclization under acidic conditions to produce the corresponding pyrroles in good overall yields. The utility of this protocol is exemplified by the synthesis of the marine alkaloids lamellarins O and Q.
A direct phosphine-mediated synthesis of pyrroles from acid chlorides and α,β-unsaturated imines
Lu, Yingdong,Arndtsen, Bruce A.
supporting information; experimental part, p. 1369 - 1372 (2009/09/05)
A one-step method to assemble pyrroles from α,β-unsaturated imines and acid chlorides has been developed. This reaction is mediated by triphenylphosphine, which eliminates phosphine oxide to allow cyclization. This reaction has been employed to access a d
Synthesis of simple 3,4-diarylpyrrole-2,5-dicarboxylic acids and lukianol A by oxidative condensation of 3-arylpyruvic acids with ammonia
Hinze, Claudia,Kreipl, Andreas,Terpin, Andreas,Steglich, Wolfgang
, p. 608 - 612 (2008/01/04)
Several derivatives of 3,4-diaryl- and 3,4-diindolylpyrrole-2,5- dicarboxylic acids including lycogalic acid A and two Halomonas metabolites were synthesized by oxidative dimerization of arylpyruvic acids or arylpyruvates in the presence of ammonia. The r
The regioselective synthesis of aryl pyrroles
Smith, Jason A.,Ng, Sarah,White, Jonathon
, p. 2477 - 2482 (2008/03/11)
Pyrrole is a unique aromatic molecule as it can readily undergo substitution at all five positions but obtaining the desired regioisomer can prove difficult to control. We now report our results on the regioselective arylation of pyrrole, utilizing select
Cyclization of functionalized ketene-N,S-acetals to substituted pyrroles: Applications in the synthesis of marine pyrrole alkaloids
Mathew, Paulson,Asokan
, p. 475 - 478 (2007/10/03)
α-Oxoketene-N,S-acetals, prepared by the reaction of alkyl glycinates with β-oxodithiocarboxylates followed by alkylation, underwent cyclization in the presence of the Vilsmeier reagent to afford alkyl 3-aryl-4-formyl-5- (alkylsulfanyl)-1H-pyrrole-2-carbo
Regioselective preparation of 2-substituted 3,4-diaryl pyrroles: A concise total synthesis of ningalin B
Bullington, James L.,Wolff, Russell R.,Jackson, Paul F.
, p. 9439 - 9442 (2007/10/03)
Methylisocyanoacetate undergoes a 2 + 3 cycloaddition with α,β-unsaturated nitriles to provide a regioselective synthesis of 2-substituted 3,4-diaryl pyrroles. The ease of preparation of α,β-unsaturated nitriles allows the rapid synthesis of pyrroles with varied substituents. Using this method, a key intermediate (1) for the synthesis of the marine natural products lukianol A, lamellarin O, and lamellarin Q was prepared in two steps. A total synthesis of ningalin B (11) was also accomplished utilizing this methodology.
Highly regioselective synthesis of 2,3,4-trisubstituted 1H-pyrroles: A formal total synthesis of lukianol A
Liu, Jian-Hui,Yang, Qing-Chuan,Mak, Thomas C. W.,Wong, Henry N. C.
, p. 3587 - 3595 (2007/10/03)
A combined use of α-lithiation and nucleophilic substitutions of N,N- dimethyl 3,4-bis(trimethylsilyl)-1H-pyrrole-1-sulfonamide 8c led to several 2-substituted 3,4-bis(trimethylsilyl)-1H-pyrrole-1-sulfonamides. Utilizing the β-effect of a trimethylsilyl group, a highly regioselective synthesis of 2,3,4-trisubstituted 1H-pyrroles 23 and 34 was accomplished. The marine natural product lukianol A (3) was prepared utilizing this strategy.
