33803-58-6Relevant academic research and scientific papers
Synthesis and Biological Evaluation of Tricyclic Guanidine Analogues of Batzelladine K for Antimalarial, Antileishmanial, Antibacterial, Antifungal, and Anti-HIV Activities
Ahmed, Nafees,Brahmbhatt, Keyur G.,Khan, Shabana I.,Jacob, Melissa,Tekwani, Babu L.,Sabde, Sudeep,Mitra, Debashis,Singh, Inder P.,Khan, Ikhlas A.,Bhutani, Kamlesh K.
, p. 491 - 498 (2013/05/21)
Fifty analogues of batzelladine K were synthesized and evaluated for in vitro antimalarial (Plasmodium falciparum), antileishmanial (Leishmania donovani), antimicrobial (panel of bacteria and fungi), antiviral (HIV-1) activities. Analogues 14h and 20l exhibited potential antimalarial activity against chloroquine-sensitive D6 strain with IC50 1.25 and 0.88μm and chloroquine-resistant W2 strain with IC50 1.64 and 1.07μm, respectively. Analogues 12c and 14c having nonyl substitution showed the most potent antileishmanial activity with IC50 2.39 and 2.78μm and IC90 11.27 and 12.76μm, respectively. Three analogues 12c, 14c, and 14i were the most active against various pathogenic bacteria and fungi with IC503.02μm and MIC/MBC/MFC 6μm. Analogue 20l having pentyl and methyl substituents on tricycle showed promising activities against all pathogens. However, none was found active against HIV-1. Our study demonstrated that the tricyclic guanidine compounds provide new structural class for broad spectrum activity. Fifty analogues of tricyclic guanidine derivative of batzelladine K were synthesized and tested for antimalarial, antileishmanial, antimicrobial, antifungal and anti-HIV activities. We have identified several active analogues.
Total synthesis of (±)-batzelladine K: A biomimetic approach
Ahmed, Nafees,Brahmbhatt, Keyur G.,Singh, Inder Pal,Bhutani, Kamlesh K.
experimental part, p. 2567 - 2570 (2010/09/10)
Total synthesis of batzelladine K was achieved by a biomimetic approach. The key reactions involve two Wittig reactions of phosphoranes and aldehydes leading to an ,-unsaturated ketone, followed by a condensation with guanidine. The synthesis was accomplished in four steps with an overall yield of 12%. The relative stereochemistry of batzelladine K was established by NOE experiments and comparison with literature values. Georg Thieme Verlag Stuttgart - New York.
Synthesis of six epoxyketooctadecenoic acid (EKODE) isomers, their generation from nonenzymatic oxidation of linoleic acid, and their reactivity with imidazole nucleophiles
Lin, De,Zhang, Jianye,Sayre, Lawrence M.
, p. 9471 - 9480 (2008/03/14)
(Chemical Equation Presented) As a class of linoleic acid oxidation products, epoxyketooctadecenoic acids (EKODEs), are formed in vivo and in vitro by a free radical mechanism initiated by either enzymatic or nonenzymatic pathways. They have so far been m
A new diastereoselective route to 5-substituted-8-methylindolizidines. Synthesis of indolizidine (-) 209B
Bardou, Anita,Celerier, Jean-Pierre,Lhommet, Gerard
, p. 5189 - 5192 (2007/10/03)
The highly diastereoselective synthesis of the indolizidine alkaloid (- ) 209B is described via the diastereoselective alkylation of a chiral cyclic β-amino ester prepared from (R)-methylbenzylamine.
A short synthetic route to the tricyclic guanidinium core of the batzelladine alkaloids
Black, Gregory P.,Murphy, Patrick J.,Walshe, Nigel D. A.
, p. 9481 - 9488 (2007/10/03)
The addition of guanidine to a series of bis-α,β-unsaturated ketones is reported leading to the formation of tricyclic guanidines, which are models of the naturally occurring batzelladine alkaloids. Nmr evidence is given in support of a new assignment for
Synhtesis of Some Aromatic Prostaglandin Analogues. Part 1
Durrant, Graham,Green, Richard H.,Lambeth, Paul F.,Lester, Michael G.,Taylor, Nigel R.
, p. 2211 - 2214 (2007/10/02)
7-heptanoic acid (4) has been prepared in six steps from 3,5-dimethoxybenzaldehyde.
Charge-Directed Conjugate Addition Reactions in the Preparation of Substituted Methyl Ketones
Cooke, Manning P.,Burman, Diana L.
, p. 4955 - 4963 (2007/10/02)
Charge-directed conjugated addition reactions of the tert-butyl esters of α,β-unsaturated acylphosphoranes 2 have been used to prepare a variety of substituted methyl ketones.Substituted ylides 6 are prepared by alkylating ylide anions 4 generated by the addition of nucleophiles to 2 and are converted under acidic conditions to substituted (acylmethylene)phosphoranes 12 which are hydrolyzed to methyl ketones.The utility of these unsaturated acylphosphoranes as methyl vinyl ketone equivalents in conjugate addition-alkylation reactions is demonstrated in a synthesis of the racemic form of the sex pheromone of the California red scale, 14.
Cyclopentanone derivatives
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, (2008/06/13)
Cyclopentane derivatives of the formula: STR1 wherein R1 represents hydrogen or a carboxylic acyl group, and either (I) R2 represents a group of the formula: (wherein R3 and R4 represent hydrogen or alkyl, and R5 represents hydrogen, or alkyl, alkoxy, cycloalkyl or adamantyl, or R5 represents alkyl substituted by alkoxy, or by cycloalkyl or by adamantyl, or the group --CR3 R4 R5 together forms a cycloalkyl or adamantyl group), X represents trans-vinylene or ethylene and Y represents carbonyl or a group of the formula: STR2 wherein R6 represents hydrogen or alkyl, and R7 represents hydrogen or a carboxylic acyl group, or else (ii) R2 represents a group of the formula: (wherein A represents alkylene, Z represents a direct bond or oxygen or sulphur, and R8 represents an aryl or heterocyclyl group which may be substituted by one or more of halogen, alkyl, alkoxy and trihalomethyl), X in formula I represents ethylene or trans-vinylene and Y in formula I represents carbonyl or a group of formula III, or else (iii) R2 represents a group R8 and X and Y in formula I represent simultaneously ethylene and carbonyl, trans-vinylene and carbonyl, or ethylene and --CH(OR7)-- groups respectively. The compounds are new and possess pharmacological properties similar to those of prostaglandins.
Organic derivatives
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, (2008/06/13)
Propanoic acid derivatives of formula: STR1 where X represents a ketonic or hydroxylic function, R1 is a C1-8 alkyl group optionally substituted by hydroxy or --COOH and R2 is hydrogen or a protecting group, having spasmolytic activity.
