352304-41-7

Usage

Uses

Used in Pharmaceutical Industry:
Butylcycloheptylprodigiosin is used as an antimalarial agent for its ability to combat malaria-causing parasites. Its effectiveness in treating this disease makes it a valuable asset in the fight against malaria, particularly in regions where the disease is prevalent.
Butylcycloheptylprodigiosin is also used as an antiulcer agent for its potential to alleviate and treat ulcers. Its antiulcer properties can be beneficial in the development of medications aimed at reducing the severity and frequency of ulcer-related symptoms.
Furthermore, Butylcycloheptylprodigiosin is used as an apoptotic agent due to its ability to induce apoptosis, or programmed cell death, in certain cells. This characteristic can be harnessed in the development of therapies for various conditions, including cancer, where the induction of apoptosis can help eliminate harmful or damaged cells.

Upstream product

• 1213263-03-6 tert-butyl 5′-formyl-4′-methoxy-1H,1′H-[2,2′-bipyrrole]-1-carboxylate 
• 857256-88-3 (Z,Z)-cyclonona-2,8-dienol 
• 33525-29-0 (Z,Z)-cyclonona-2,8-dienone 
• 857256-81-6 2-methyl-7,8,9,10-tetrahydro-6H-cyclonona[b]pyrrole-1-carboxylic acid tert-butyl ester 
• 857256-75-8 2-methyl-1,6,7,8,9,10-hexahydro-cyclonona[b]pyrrole 
• 857256-89-4 ((2Z,8Z)-1-Cyclonona-2,8-dienyl)-propan-2-one oxime 
• 857256-80-5 (4Z,9Z)-2-Methyl-3,3a,6,7,8,10a-hexahydro-cyclonona[b]pyrrole 
• 857256-76-9 cyclonona-(Z,Z)-2,8-dienylacetone 
• 857256-77-0 (Z,Z)-cyclonona-2,8-dienyl acetate 
• 42052-30-2 (Z)-cyclonon-2-enone 
• 69778-83-2 4-methoxy-3-pyrrolin-2-one 
• 940288-03-9 C₁₇H₂₅NO₂ 
• 940288-02-8 C₁₇H₂₅NO₂ 
• 940288-00-6 C₁₆H₂₅NO 

Relevant academic research and scientific papers

A concise synthesis of butylcycloheptylprodigiosin

A short and efficient total synthesis of the tripyrrole alkaloid butylcycloheptylprodigiosin is described. Key to the brevity of the approach is a two-step synthesis of macrocyclic formylpyrrole 4 from cyclononenone 6.

Elimination of butylcycloheptylprodigiosin as a known natural product inspired by an evolutionary hypothesis for cyclic prodigiosin biosynthesis

The cyclic prodigiosins are an important family of bioactive natural products that continue to be the subject of numerous structural, synthetic, and biosynthetic studies. In particular, the structural assignments of the isomeric cyclic prodigiosins butylcycloheptylprodigiosin (BCHP) and streptorubin B have been the cause of significant confusion. Herein, we report detailed studies regarding the electron impact (EI) mass spectra of synthetic BCHP and streptorubin B that have allowed us to distinguish the two compounds in the absence of quality historical isolation NMR data. On the basis of these fragmentation differences, the status of BCHP as a natural product is challenged. The proposed mechanism of fragmentation is supported by the EI mass spectra of synthetic pentyl-chain analogues of BCHP and streptorubin B, X-ray crystallography, and DFT calculations. Elimination of BCHP from the prodigiosin family supports a proposed evolutionary hypothesis for the surprising biosynthesis of cyclic prodigiosins.

Total synthesis, molecular editing and evaluation of a tripyrrolic natural product: The case of "butylcycloheptylprodigiosin"

Conflicting reports are found in the literature on whether the ortho-pyrrolophane derivative 6, which has been named " butylcycloheptylprodigiosin" even though it is a cyclononane derivative, is a natural product or merely a mis-assigned structure. This dispute has now been resolved by an unambiguous total synthesis of this complex alkaloid which confirms the initial structure assignment. The chosen approach is largely catalysis-based, featuring the first application of a "Narasaka-Heck" reaction in natural product chemistry. This palladium-catalyzed transformation allows the unsaturated oxime ester 26 to be converted into the bicyclic dihydropyrrole 27. Other notable reactions of the reported approach to 6 are a regioselective Tsuji-Trost reaction of the doubly allylic acetate 21 with methyl acetoacetate. a base-induced aromatization of 27 to the corresponding pyrrole 28. a chemoselective oxidation of the benzylic methyl group in 33 with cerium ammonium nitrate in a biphasic reaction medium that does not affect the labile pyrrole nucleus, and a Suzuki cross-coupling for the completion of the heterocyclic domain. Diversification in the latter step leads to a set of analogues that differ from the natural product in the terminal (hetero)arene ring. This structural modification results in complete loss of the very pronounced ability of the parent compound 6 to induce oxidative cleavage in double stranded DNA in the presence of Cu11. Several cyclononane-, cyclononene- and cyclononadiene derivatives prepared en route to 6 have been characterized by crystal structure analysis, allowing the conformational behavior of nine-membered carbocycles to be studied.

Chasing a phantom by total synthesis: The butylcycloheptylprodigiosin case

The dispute as to whether "butylcycloheptylprodigiosin" is a natural product or solely a misassigned structure lasted for more than a decade. This open question has now been answered by the first total synthesis of this tripyrrole alkaloid (see picture),