51116-73-5Relevant academic research and scientific papers
Extending the Salinilactone Family
Schlawis, Christian,Harig, Tim,Ehlers, Stephanie,Guillen-Matus, Dulce G.,Creamer, Kaitlin E.,Jensen, Paul R.,Schulz, Stefan
, p. 1629 - 1632 (2020)
Five new members of the salinilactone family, salinilactones D–H, are reported. These bicyclic lactones are produced by Salinispora bacteria and display extended or shortened alkyl side chains relative to the recently reported salinilactones A–C. They were identified by GC/MS, gas chromatographic retention index, and comparison with synthetic samples. We further investigated the occurrence of salinilactones across six newly proposed Salinispora species to gain insight into how compound production varies among taxa. The growth-inhibiting effect of this compound family on multiple biological systems including non-Salinispora actinomycetes was analyzed. Additionally, we found strong evidence for significant cytotoxicity of the title compounds.
Pheromone synthesis. Part 259: Synthesis of seven methyl-branched hydrocarbons as the pheromone candidates for female Korean apricot wasp, Eurytoma maslovskii
Mori, Kenji,Yang, Chang Yeol
, p. 4593 - 4607 (2016/07/07)
Seven new methyl-branched hydrocarbons were synthesized, which were the pheromone candidates of the female Korean apricot wasp (Eurytoma maslovskii). They are (Z)-15-methyl-7-nonacosene (1), (Z)-17-methyl-7-hentriacontene (2), 3,7-dimethylheptacosane (3), 8,12-dimethyltriacontane (4), 8,18-dimethyltriacontane (5), 3,7,11-trimethylnonacosane (6), and 3,7,17-trimethylnonacosane (7). All of them were synthesized as stereoisomeric mixtures, employing short and simple routes. Hydrocarbon 7 was synthesized via 4,8-dimethyldecanal (71, tribolure), the red flour beetle pheromone. The hydrocarbons 1,2,3 and 6 were identified by GC–MS analysis as the components (with unknown stereochemistry) of the female-specific secretion of E. maslovskii.
Macrolides and alcohols as scent gland constituents of the Madagascan frog mantidactylus femoralis and their intraspecific diversity
Poth, Dennis,Peram, Pardha Saradhi,Vences, Miguel,Schulz, Stefan
supporting information, p. 1548 - 1558 (2013/10/22)
Acoustic and, to a lesser degree, visual signals are the predominant means of signaling in frogs. Nevertheless, certain lineages such as the mantelline frogs from Madagascar use the chemical communication channel as well. Males possess femoral glands on the hind legs, which recently have been shown to contain volatile compounds used in communication as pheromones. Many mantelline species occur in sympatry, and so far species recognition is regarded to occur mainly by acoustic signals. The analysis of the gland constituents of Mantidactylus femoralis by GC/MS revealed the presence of volatile macrolides and secondary alcohols. The new natural products mantidactolides A (4) and B (6), as well as several methyl carbinols, were identified, and their structures were confirmed by synthesis. The analysis of individuals from different locations of Madagascar revealed the presence of two groups characterized by specific patterns of compounds. While one group contained the alcohols and mantidactolide B, the other showed specific presence of the macrolides phoracantholide I (1) and mantidactolide A (4). Genetic analysis of some individuals showed no congruence between genetic relatedness and gland constituents. Several other individuals from related species had different gland compositions. This suggests that a basic set of biosynthetic machinery might be available to a broader group of related species.
Novel fatty acid methyl esters from the actinomycete Micromonospora aurantiaca
Dickschat, Jeroen S.,Bruns, Hilke,Riclea, Ramona
supporting information; experimental part, p. 1697 - 1712 (2012/02/04)
The volatiles released by Micromonospora aurantiaca were collected by means of a closed-loop stripping apparatus (CLSA) and analysed by GC-MS. The headspace extracts contained more than 90 compounds from different classes. Fatty acid methyl esters (FAMEs) comprised the major compound class including saturated unbranched, monomethyl and dimethyl branched FAMEs in diverse structural variants: Unbranched, α-branched, γ-branched, (ω-1)-branched, (ω-2)-branched, α-and (ω-1)-branched, γ-and (ω-1)-branched, γ-and (ω-2)-branched, and γ-and (ω-3)-branched FAMEs. FAMEs of the last three types have not been described from natural sources before. The structures for all FAMEs have been suggested based on their mass spectra and on a retention index increment system and verified by the synthesis of key reference compounds. In addition, the structures of two FAMEs, methyl 4,8-dimethyldodecanoate and the ethyl-branched compound methyl 8-ethyl-4-methyldodecanoate were deduced from their mass spectra. Feeding experiments with isotopically labelled [ 2H10]leucine, [2H10]isoleucine, [2H8]valine, [2H5]sodium propionate, and [methyl-2H3]methionine demonstrated that the responsible fatty acid synthase (FAS) can use different branched and unbranched starter units and is able to incorporate methylmalonyl-CoA elongation units for internal methyl branches in various chain positions, while the methyl ester function is derived from S-adenosyl methionine (SAM).
Histamine H3 and H4 receptor affinity of branched 3-(1H-imidazol-4-yl)propyl N-alkylcarbamates
?azewska, Dorota,Wiecek, Ma?gorzata,Ligneau, Xavier,Kottke, Tim,Weizel, Lilia,Seifert, Roland,Schunack, Walter,Stark, Holger,Kie?-Kononowicz, Katarzyna
scheme or table, p. 6682 - 6685 (2010/06/16)
A series of imidazole-containing (non-)chiral carbamates were tested at human histamine H3 receptor (H3R). All compounds displayed Ki values below 100 nM. A trend for a stereoselectivity at human H3R was observed for the chiral α-branched ligands. Selected compounds were also tested at human histamine H4 receptor and showed moderate to weak affinities (118-1460 nM).
Development of chiral N-alkylcarbamates as new leads for potent and selective H3-receptor antagonists: Synthesis, capillary electrophoresis, and in vitro and oral in vivo activity
Sasse, Astrid,Kiec-Kononowicz, Katarzyna,Stark, Holger,Motyl, Malgorzata,Reidemeister, Sibylle,Ganellin, C. Robin,Ligneau, Xavier,Schwartz, Jean-Charles,Schunack, Walter
, p. 593 - 600 (2007/10/03)
Novel carbamates as derivatives of 3-(1H-imidazol-4-yl)propanol with an N-alkyl chain were prepared as histamine H3-receptor antagonists. Branching of the N-alkyl side chain with methyl groups led to chiral compounds which were synthesized stereospecifically by a Mitsunobu protocol adapted Gabriel synthesis. The optical purity of some of the chiral compounds was determined (ee > 95%) by capillary electrophoresis (CE). The investigated compounds showed pronounced to high antagonist activity (K(i) values of 4.1-316 nM) in a functional test for histamine H3 receptors on rat cerebral cortex synaptosomes. Similar H3-receptor antagonist activities were observed in a peripheral model on guinea pig ileum. No stereoselective discrimination for the H3 receptor for the chiral antagonists was found with the in vitro assays. All compounds were also screened for central H3-receptor antagonist activity in vivo in mice after po administration. Most compounds were potent agents of the H3-receptor-mediated enhancement of brain N(τ)- methylhistamine levels. The enantiomers of the N-2-heptylcarbamate showed a stereoselective differentiation in their pharmacological effect in vivo (ED50 of 0.39 mg/kg for the (S)-derivative vs 1.5 mg/kg for the (R)- derivative) most probably caused by differences in pharmacokinetic parameters. H1- and H2-receptor activities were determined for some of the novel carbamates, demonstrating that they have a highly selective action at the histamine H3 receptor.
The Synthesis and Mesomorphic Properties of 4-Methyl-Pentyloxyphenylthio-4'-Substituted Benzoates
Neubert, M. E.,Shenouda, I. G.
, p. 29 - 45 (2007/10/02)
Three different series of branched chain alkoxy thioesters of the type p-X-C6H4-C(O)S-C6H4-p-O(CH2)mCH(CH3)(CH2)nCH3 with m = 0-3, n = 3-0; X = R, RO and C9CO2 and R varying between C6 and C12 were synthesized by esterification of 4-substituted benzoic acids with the branched chain alkoxy thiol using the carbodiimide method.Mesomorphic properties were determined by hot-stage polarizing microscopy and compared with those for analogous straight-chain thioesters.Clearing temperatures were always lower in the branched chain than in the straight chain series, but the amount of lowering decreased as the methyl group was moved out along the branched chain away from the benzene ring.Melting temperatures were more variable, as expected, often showing little variation between the 1,2 and 2,1 isomers but increasing considerably for the 3,0 isomer until temperatures were either equal to or slightly higher than those in the straight-chain compounds.The smectic C phase was enhanced usually at the expense of the nematic phase.Nematic-smectic C combinations predominated with the smectic A phase occurring as a short phase range only in the RO-2,1 and X = R series.The most mesophases were usually observed in the 2,1 series; moving the methyl group further out along the chain tended to give restoration of the nematic phase as the predominant phase.The biphenyl thioester p-C8H17O-C6H4-C6H4-C(O)S-C6H4-p-OCH2CH2CH(Me)Et was also synthesized and showed an enantiotropic sequence of SC, SA and N phases with a monotropic smectic G phase which supercooled considerably.Transition temperatures were all > 100 deg C.The thiols with m > 0 were prepared by alkylation of sodium 4-hydroxybenzene-sulfonate with the branched chain bromide, conversion to the sulfonyl chloride and reduction to the thiol.When m = 0, synthesis was by alkylation of 4-bromophenol with the branched chain bromide, treatment with cuprous thiobutane and cleavage of the butyl group with NaNH2.
The Effect of Methyl Group Position in Branched Alkyl Chains on the Phenolic End of 4,4'-Disubstituted Phenylbenzoates on Mesomorphic Properties and Some Optically Active Analogs as Ferroelectric Liquid Crystals
Neubert, M. E.,Leonhardt, D.,Sabol-Keast, S.
, p. 227 - 248 (2007/10/02)
A select number of homologs of the branched chain (BC) C5 ester series: in which m=0-3 and n=0-2, and X=R, RO, and C9CO2 have been synthesized to study the effect of branching and the position of the branching methyl group on mesomorphic propert
