The Synthesis of (R)-2',3'-Dihydroxypropyl 5-Deoxy-5-Dimethylarsinyl-β-D-Riboside, a Naturally Occurring Arsenic-Containing Carbohydrate

1987 ◽  
Vol 40 (11) ◽  
pp. 1901 ◽  
Author(s):  
DP Mcadam ◽  
AMA Perera ◽  
RV Stick
Keyword(s):  
Natural Product ◽  
Hydroxy Group ◽  
Title Compound ◽  
Protecting Groups ◽  
Giant Clam ◽  
Free Hydroxy Group ◽  
Naturally Occurring ◽  
Step Procedure ◽  
Tridacna Maxima ◽  
Subsequent Chemical

The synthesis of the title compound, isolated from the brown kelp ( Ecklonia radiata ) or the giant clam (Tridacna maxima), is reported. Glycosidation of 1-O-acetyl-2,3,5-tri- O- benzoyl -β-D-ribose, either directly with (S)-1,2-di-O-benzylglycerol or via the derived orthoester with (S)-1,2-O-isopropylideneglycerol, led to two fully protected glycerol β-D- ribofuranosides. Subsequent chemical manipulations led to a common intermediate having a free hydroxy group at C5 of the D-ribose residue. Replacement of this hydroxy group by a chlorine atom allowed the introduction of the dimethylarsinyl group at C5 in a two-step procedure, and removal of protecting groups provided the natural product.

Synthesis of (15E)-17β-hydroxy-5α-androstane-3,15-dione 15-[O-(Carboxymethyl)]oxime, New Hapten for Dihydrotestosterone (17β-hydroxy-5α-androstan-3-one)

1997 ◽  
Vol 62 (10) ◽  
pp. 1642-1649 ◽  
Author(s):  
Ivan Černý ◽  
Tereza Slavíková ◽  
Vladimír Pouzar
Keyword(s):  
Hydroxy Group ◽  
Carboxy Group ◽  
Title Compound ◽  
Oxidative Cleavage ◽  
Hydroxy Derivative ◽  
Borohydride Reduction ◽  
Protecting Group ◽  
Free Hydroxy Group

Addition of 4-methoxybenzyl alcohol to 3β-hydroxy-5α-androst-15-en-17-one gave the mixture of isomeric 15-(4-methoxyphenyl)methoxy derivatives from which, after acetylation and chromatography, the major 15β isomer was separated. Borohydride reduction gave 17β-hydroxy derivative which was protected as methoxymethyl ether. Oxidative cleavage of protecting group at position 15 and the subsequent Jones oxidation afforded corresponding 15-ketone. Its oximation with O-(carboxymethyl)hydroxylamine, deacetylation and methylation with diazomethane gave protected O-(carboxymethyl)oxime derivative with free hydroxy group at position 3. Its oxidation afforded dihydrotestosterone derivative and successive deprotection of position 17 and of carboxy group led to final (15E)-17β-hydroxy-5α-androstane-3,15-dione 15-[O-(carboxymethyl)]oxime. The title compound was designed as dihydrotestosterone hapten for heterologous radioimmunoassays.

scholarly journals Tissue-Specific Microbiomes of the Red Sea Giant Clam Tridacna maxima Highlight Differential Abundance of Endozoicomonadaceae

2019 ◽  
Vol 10 ◽  
Author(s):  
Susann Rossbach ◽  
Anny Cardenas ◽  
Gabriela Perna ◽  
Carlos M. Duarte ◽  
Christian R. Voolstra
Keyword(s):  
Red Sea ◽  
Giant Clam ◽  
Differential Abundance ◽  
Tissue Specific ◽  
Tridacna Maxima

scholarly journals New Pharmacological Opportunities for Betulinic Acid

Planta Medica ◽  
2017 ◽  
Vol 84 (01) ◽  
pp. 8-19 ◽  
Author(s):  
José Ríos ◽  
Salvador Máñez
Keyword(s):  
Metabolic Syndrome ◽  
Natural Product ◽  
Betulinic Acid ◽  
Therapeutic Potential ◽  
Present Review ◽  
Antitumor Effects ◽  
Pharmacological Activities ◽  
Naturally Occurring ◽  
Wide Range ◽  
Birch Trees

AbstractBetulinic acid is a naturally occurring pentacyclic lupane-type triterpenoid usually isolated from birch trees, but present in many other botanical sources. It is found in different plant organs, both as a free aglycon and as glycosyl derivatives. A wide range of pharmacological activities has been described for this triterpenoid, including antiviral and antitumor effects. In addition, several other interesting properties have been identified in the fields of immunity and metabolism, namely antidiabetic, antihyperlipidemic, and anti-inflammatory activities. Taken together, these latter three properties make betulinic acid a highly interesting prospect for treating metabolic syndrome. The present review focuses on the therapeutic potential of this agent, along with several of its semisynthetic derivatives, which could open new frontiers in the use of natural product-based medicines.

scholarly journals Total Syntheses of Pladienolide-Derived Spliceosome Modulators

Molecules ◽  
2021 ◽  
Vol 26 (19) ◽  
pp. 5938
Author(s):  
Jaehoon Sim ◽  
Eunbin Jang ◽  
Hyun Jin Kim ◽  
Hongjun Jeon
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Structural Features ◽  
Synthetic Approach ◽  
Synthetic Analog ◽  
Phase I Clinical Trials ◽  
Total Syntheses ◽  
Naturally Occurring ◽  
Anti Cancer ◽  
Synthetic Approaches

Pladienolides, an emerging class of naturally occurring spliceosome modulators, exhibit interesting structural features, such as highly substituted 12-membered macrocycles and epoxide-containing diene side chains. The potential of pladienolides as anti-cancer agents is confirmed by H3B-8800, a synthetic analog of this natural product class, which is currently under Phase I clinical trials. Since its isolation in 2004 and the first total synthesis in 2007, a dozen total syntheses and synthetic approaches toward the pladienolide class have been reported to date. This review focuses on the eight completed total syntheses of naturally occurring pladienolides or their synthetic analogs, in addition to a synthetic approach to the main framework of the natural product.

scholarly journals Crystal structure of racemic [(1R,2S,3R,4S,6S)-2,6-bis(furan-2-yl)-4-hydroxy-4-(thiophen-2-yl)cyclohexane-1,3-diyl]bis(thiophen-2-ylmethanone)

2016 ◽  
Vol 72 (7) ◽  
pp. 976-979 ◽  
Author(s):  
Ísmail Çelik ◽  
Cem Cüneyt Ersanlı ◽  
Mehmet Akkurt ◽  
Hayrettin Gezegen ◽  
Rahmi Köseoğlu
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Hydroxy Group ◽  
Title Compound ◽  
Furan Ring ◽  
Chair Conformation ◽  
Cyclohexane Ring ◽  
Π Interactions ◽  
Compound C

In the title compound, C28H22O5S3, the central cyclohexane ring adopts a chair conformation. The atoms of the furan ring attached to the 6-position of the central cyclohexane ring are disordered over two sets of sites with occupancies of 0.832 (5) and 0.168 (5). The hydroxy group is disordered over two positions (at the 4- and 6-positions of the cyclohexane ring) in the ratio 0.832 (5):0.168 (5). In the crystal, molecules are linked by C—H...O hydrogen bonds and C—H...π interactions, forming layers parallel to (100).

N-{(2RS)-2-Hydroxy-3-[2-(3-phenylpropanoyl)phenoxy]propyl}propanaminium chloride

2006 ◽  
Vol 62 (5) ◽  
pp. o1694-o1695
Author(s):  
Massimo Bambagiotti-Alberti ◽  
Bruno Bruni ◽  
Ferdinando Costantino ◽  
Massimo Di Vaira ◽  
Valerio Giannellini
Keyword(s):  
Hydrogen Bonds ◽  
Hydroxy Group ◽  
Antiarrhythmic Drug ◽  
Sodium Transport ◽  
Title Compound ◽  
Crystal Packing ◽  
Chloride Ion

The title compound, propafenone hydrochloride, C21H28NO3 +·Cl−, is a potent antiarrhythmic drug, which acts by blocking channels for sodium transport across cell borders. The crystal packing is essentially controlled by a system of hydrogen bonds involving the quaternary N atom, the (disordered) hydroxy group and the chloride ion.

scholarly journals 4-[(E)-(4-Hydroxybenzylidene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione

2014 ◽  
Vol 70 (6) ◽  
pp. o733-o734 ◽  
Author(s):  
Balladka K. Sarojini ◽  
Padmanabha S. Manjula ◽  
B. Narayana ◽  
Jerry P. Jasinski
Keyword(s):  
Hydrogen Bonds ◽  
Intermolecular Interactions ◽  
Hydroxy Group ◽  
Title Compound ◽  
Triazole Ring ◽  
Compound C ◽  
Centroid Distance ◽  
Group Form ◽  
The Mean ◽  
Graph Set

The title compound, C10H10N4OS, is nearly planar with the mean planes of the hydroxybenzyl and triazole rings inclined at an angle of only 3.2 (7)°. In the crystal, O—H...N hydrogen bonds between the hydroxy group and the triazole ring in concert with weak N—H...S intermolecular interactions between the triazole ring and thione group form chains along [-210] enclosingR22(8) graph-set motifs. A weak intramolecular C—H...S interaction and intermolecular π–π interactions [centroid–centroid distance = 3.5990 (15) Å] are also observed.

scholarly journals Scalable Preparation of Enantioenriched (S)-5-methylhept-2-en-4-one. Synthesis and Aroma Properties of Achiral Analogues Thereof

Molecules ◽  
2019 ◽  
Vol 24 (24) ◽  
pp. 4497
Author(s):  
Eva Puchľová ◽  
Michal Dendys ◽  
Ivan Špánik ◽  
Peter Szolcsányi
Keyword(s):  
Natural Product ◽  
Title Compound ◽  
Structural Changes ◽  
Chemoenzymatic Synthesis ◽  
Synthetic Analogues ◽  
Purification Method ◽  
Flavour Compound ◽  
Sensory Analyses ◽  
And Shifts

(S)-5-Methylhept-2-en-4-one is a key flavour compound in hazelnuts. We have performed its chiral-pool-based chemoenzymatic synthesis with 39% overall yield (73% ee). The four-step aldol-based sequence avoids the use of highly reactive and/or toxic reagents, does not require anhydrous conditions and uses only distillation as the purification method. Thus, such methodology represents a green and scalable alternative to only two stereoselective approaches towards this natural product known so far. In addition, we have designed and prepared a set of new (di)enones as achiral synthetic analogues of the title compound. The results of their sensory analyses clearly show that relatively minor structural changes of the natural molecule significantly alter its olfactory properties. Thus, simple (poly)methylation completely changes the original hazelnut aroma of (S)-5-methylhept-2-en-4-one and shifts the odour of its analogues to eucalyptus, menthol, camphor, and sweet aroma.

Versuche zur Synthese natürlich vorkommender prenylierter Naphthalinderivate. Nachweis eines neuen Prenylnaphthochinon- derivates in Galium mollugo / Synthesis of Naturally Occurring Prenylated Naphthalene Derivates. Isolation of a New Prenylnaphthoquinone from Galium mollugo

1982 ◽  
Vol 37 (5-6) ◽  
pp. 354-362 ◽  
Author(s):  
Lutz Heide ◽  
Eckhard Leistner
Keyword(s):  
Natural Product ◽  
Root System ◽  
Spectroscopic Methods ◽  
Naphthalene Derivatives ◽  
Naturally Occurring

AbstractSeveral prenylated naphthalene derivatives were synthesized and characterized by spectroscopic methods. One of these compounds, 2-methoxycarbonyl-3-prenyl-1,4-naphthoquinone, was detected as a new natural product in the root system of Galium mollugo L. This new natural product is likely to be related to the biosynthesis of mollugin and anthraquinones.

scholarly journals Metabarcoding reveals distinct microbiotypes in the giant clam Tridacna maxima

Microbiome ◽  
2020 ◽  
Vol 8 (1) ◽  
Author(s):  
Isis Guibert ◽  
Gael Lecellier ◽  
Gergely Torda ◽  
Xavier Pochon ◽  
Véronique Berteaux-Lecellier
Keyword(s):  
Giant Clam ◽  
Tridacna Maxima
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