6246-48-6

Usage

Uses

Used in Organic Synthesis:
GERANYLAMINE is used as a starting reagent for the total synthesis of Nitensidine D, a naturally occurring guanidine alkaloid. It plays a crucial role in the synthesis process, enabling the formation of the desired compound.
Used in Benzoquinone Synthesis:
GERANYLAMINE is also used as a starting reagent for the synthesis of 5-alkylaminoand 2,5-bis(alkylamino)-[1,4]-benzoquinone. Its presence in the reaction allows for the formation of these benzoquinone derivatives, which have potential applications in various fields.

Upstream product

• 172161-69-2 geranial oxime 
• 105-87-3 3,7-dimethyl-2E,6-octadien-1-yl acetate 
• 5146-66-7 geranonitrile 
• 110-93-0 6-Methyl-hept-5-en-2-on 
• 36615-20-0 (E)-2‐(3,7‐dimethylocta‐2,6‐dien‐1‐yl)isoindoline‐1,3‐dione 
• 5389-87-7 1-chloro-3,7-dimethylocta-2,6-diene 
• 60699-32-3 (E)-3,7-dimethylocta-2,6-dien-1-yl diethyl phosphate 
• 115-95-7 linalool acetate 
• 141-12-8 neryl acetate 
• 6138-90-5 trans-geranyl bromide 
• 106-24-1 Geraniol 
• 103953-71-5 1-geranylazacyclopentan-2,5-dione 
• 84457-88-5 (E)-1-azido-3,7-dimethylocta-2,6-diene 

Downstream Products

• 5585-39-7 (E)-3,7-dimethylocta-2,6-dienenitrile 
• 65559-74-2 (E)-N-(3,7-dimethylocta-2,6-dienyl)aniline 
• 36615-20-0 (E)-2‐(3,7‐dimethylocta‐2,6‐dien‐1‐yl)isoindoline‐1,3‐dione 
• 124658-85-1 (E)-N-(3,7-dimethylocta-2,6-dien-1-yl)-4-methylbenzenesulfonamide 

Relevant academic research and scientific papers

ETHYLENEDIAMINE COMPOUND AND USE THEREOF

The present invention relates to the field of medicinal chemistry, and relates to an ethylenediamine compound represented by Formula A, pharmaceutically acceptable salts, stereoisomers, tautomers or isomer mixtures, hydrates thereof, solvates thereof, or prodrugs thereof, and use thereof in the treatment of tuberculosis.

New hybrid compounds combining fragments of usnic acid and monoterpenoids for effective tyrosyl-dna phosphodiesterase 1 inhibition

Usnic acid (UA) is a secondary metabolite of lichens that exhibits a wide range of biological activities. Previously, we found that UA derivatives are effective inhibitors of tyrosyl-DNA phosphodiesterase 1 (TDP1). It can remove covalent complex DNA-topoisomerase 1 (TOP1) stabi-lized by the TOP1 inhibitor topotecan, neutralizing the effect of the drugs. TDP1 removes damage at the 3′ end of DNA caused by other anticancer agents. Thus, TDP1 is a promising therapeutic target for the development of drug combinations with topotecan, as well as other drugs for cancer treatment. Ten new UA enamino derivatives with variation in the terpene fragment and substituent of the UA backbone were synthesized and tested as TDP1 inhibitors. Four compounds, 11a-d, had IC50 values in the 0.23–0.40 μM range. Molecular modelling showed that 11a-d, with relatively short aliphatic chains, fit to the important binding domains. The intrinsic cytotoxicity of 11a-d was tested on two human cell lines. The compounds had low cytotoxicity with CC50 ≥ 60 μM for both cell lines. 11a and 11c had high inhibition efficacy and low cytotoxicity, and they enhanced topotecan’s cyto-toxicity in cancerous HeLa cells but reduced it in the non-cancerous HEK293A cells. This “protec-tive” effect from topotecan on non-cancerous cells requires further investigation.

ANTIBIOTIC COMPOUNDS

Provided herein are lipidated glycopeptide compounds of formula (I); or a pharmaceutically acceptable salt, stereoisomer, solvate, or prodrug thereof. R1 is a lipid, R2 is -H or a lipid, and R3 and R4 are as defined herein. These compounds have antibiotic activity. Also provided are formulations comprising such compounds; as well as such compounds or formulations for use as a medicament. The compounds and formulations may also be used in the treatment of bacterial infection.

New chemical agents based on adamantane-monoterpene conjugates against orthopoxvirus infections

Currently, the spectrum of agents against orthopoxviruses, in particular smallpox, is very narrow. Despite the fact that smallpox is well controlled, there is, for many reasons, a real threat of epidemics associated with this or a similar virus. In order to search for new low molecular weight orthopoxvirus inhibitors, a series of amides combining adamantane and monoterpene moieties were synthesized using 1- and 2-adamantanecarboxylic acids as well as myrtenic, citronellic and camphorsulfonic acids as acid components. The produced compounds exhibited high activity against the vaccinia virus (an enveloped virus belonging to the poxvirus family), which was combined with low cytotoxicity. Some compounds had a selectivity index higher than that of the reference drug cidofovir; the highest SI = 1123 was exhibited by 1-adamantanecarboxylic acid amide containing the (-)-10-amino-2-pinene moiety. The produced compounds demonstrated inhibitory activity against other orthopoxviruses: cowpox virus (SI = 30-406) and ectromelia virus (mousepox virus, SI = 39-707). This journal is

3,3-Dimethoxypropylsulfonyl Group: A new versatile protecting and activating group for amine synthesis

3,3-Dimethoxypropylsulfonyl (Dimps) chloride was prepared and used as a new versatile sulfonating agent for ammonia, primary and secondary amines to afford corresponding Dimps-amides in excellent yields. The resulting N-nonsubstituted and N-monosubstituted Dimps-amides, activated amines, were alkylated satisfactorily under new Mitsunobu conditions. The Dimps group was removed by treatment in aqueous solution under acidic followed by basic conditions. Furthermore, epilachnene, the defensive droplets from the Mexican bean beetle, Epilachna varivestis, was synthesized utilizing this Dimps methodology in short steps.

Exploiting the Synthetic Potential of Sesquiterpene Cyclases for Generating Unnatural Terpenoids

The substrate flexibility of eight purified sesquiterpene cyclases was evaluated using six new heteroatom-modified farnesyl pyrophosphates, and the formation of six new heteroatom-modified macrocyclic and tricyclic sesquiterpenoids is described. GC-O analysis revealed that tricyclic tetrahydrofuran exhibits an ethereal, peppery, and camphor-like olfactoric scent.

Antiparasitic activity of sulfur- and fluorine-containing bisphosphonates against trypanosomatids and apicomplexan parasites

Based on crystallographic data of the complexes 2-alkyl(amino)ethyl-1,1-bisphosphonates-Trypanosoma cruzi farnesyl diphosphate synthase, some linear 1,1-bisphosphonic acids and other closely related derivatives were designed, synthesized and biologically evaluated against T. cruzi, the responsible agent of Chagas disease and against Toxoplasma gondii, the etiologic agent of toxoplasmosis and also towards the target enzymes farnesyl pyrophosphate synthase of T. cruzi (TcFPPS) and T gondii (TgFPPS), respectively. The isoprenoid-containing 1,1-bisphosphonates exhibited modest antiparasitic activity, whereas the linear α-fluoro-2-alkyl(amino)ethyl-1,1-bisphosphonates were unexpectedly devoid of antiparasitic activity. In spite of not presenting efficient antiparasitic activity, these data turned out to be very important to establish a structural activity relationship.

Computer-aided rational design of novel EBF analogues with an aromatic ring

Odorant binding proteins (OBPs) are important in insect olfactory recognition. These proteins bind specifically to insect semiochemicals and induce their seeking, mating, and alarm behaviors. Molecular docking and molecular dynamics simulations were performed to provide computational insight into the interaction mode between AgamOBP7 and novel (E)-β-farnesene (EBF) analogues with an aromatic ring. The ligand-binding cavity in OBP7 was found to be mostly hydrophobic due to the presence of several nonpolar residues. The interactions between the EBF analogues and the hydrophobic residues in the binding cavity increased in strength as the distance between them decreased. The EBF analogues with an N-methyl formamide or ester linkage had higher docking scores than those with an amide linkage. Moreover, delocalized π–π and electrostatic interactions were found to contribute significantly to the binding between the ligand benzene ring and nearby protein residues. To design new compounds with higher activity, four EBF analogues D1–D4 with a benzene ring were synthesized and evaluated based on their docking scores and binding affinities. D2, which had an N-methyl formamide group linkage, exhibited stronger binding than D1, which had an amide linkage. D4 exhibited particularly strong binding due to multiple hydrophobic interactions with the protein. This study provides crucial foundations for designing novel EBF analogues based on the OBP structure. [Figure not available: see fulltext.]

First total synthesis of a guanidine alkaloid Nitensidine D using immobilized ionic liquid, microwaves and formamidinesulfinic acid

An efficient first total synthesis of a naturally occurring guanidine alkaloid, Nitensidine D isolated from ethanol extract of Pterogyne nitens has been described. Geraniol has been used as the starting material. N-alkylation of phthalimide has been achieved using immobilized ionic liquid and formamidinesulfinic acid acts as the guanylating reagent. [Figure not available: see fulltext.]

Effect of acyclic monoterpene alcohols and their derivatives on TRP channels

A series of thirty-six geraniol, nerol, citronellol, geranylamine, and nerylamine derivatives was synthesized and tested on TRPA1, TRPM8, and TRPV1 channels. Most of them acted as strong modulators of TRPA1 channels with EC50 and/or IC50 values 1 μM. None was able to significantly activate TRPM8 channels, while thirteen of them behaved as 'true' TRPM8 antagonists. Little or no effect was generally observed on TRPV1 channels. Some of the compounds examined, that is, compounds 1d,g,n, 2c,d,h,i,o, 3b,e exhibited an appreciable selectivity for TRPA1 subtype.