60902-45-6

Usage

Chemical Properties

white powder

InChI:InChI=1/C27H34P.BrH/c1-2-3-4-5-6-7-17-24-28(25-18-11-8-12-19-25,26-20-13-9-14-21-26)27-22-15-10-16-23-27;/h8-16,18-23H,2-7,17,24H2,1H3;1H/q+1;/p-1

Upstream product

• 693-58-3 1-Bromononane 
• 603-35-0 triphenylphosphine 

Downstream Products

• 1120-34-9 methyl cis-13-docosenoate 
• 7439-44-3 brassidic acid methyl ester 
• 174363-83-8 [2-(2-Amino-4-decyl-phenyl)-1-hydroxymethyl-ethyl]-carbamic acid tert-butyl ester 
• 763059-86-5 2-Amino-3-[4-((E)-dec-1-enyl)-2-nitro-phenyl]-propionic acid ethyl ester 
• 168965-49-9 [2-(4-Decyl-2-methylamino-phenyl)-1-hydroxymethyl-ethyl]-carbamic acid tert-butyl ester 
• 168965-46-6 {2-[4-((E)-Dec-1-enyl)-2-nitro-phenyl]-1-hydroxymethyl-ethyl}-carbamic acid tert-butyl ester 
• 168965-45-5 2-tert-Butoxycarbonylamino-3-[4-((E)-dec-1-enyl)-2-nitro-phenyl]-propionic acid ethyl ester 
• 169106-26-7 2-{[2-(2-tert-Butoxycarbonylamino-3-hydroxy-propyl)-5-decyl-phenyl]-methyl-amino}-3-methyl-butyric acid benzyl ester 
• 72561-88-7 (Z,Z,Z)-3,6,9-Octadecatriene 
• 169304-58-9 (5S,8R,8aS)-8-Benzyloxy-5-dodec-3'-enyloxazolo<3,4-a>piperidin-3-one 
• 89102-36-3 (5R,6S)-6-hydroxyhexadecan-5-olide 

Relevant academic research and scientific papers

Antiferroptotic Activity of Phenothiazine Analogues: A Novel Therapeutic Strategy for Oxidative Stress Related Disease

Ferroptosis is an iron-catalyzed, nonapoptotic form of regulated necrosis that has been implicated in the pathological cell death associated with various disorders including neurodegenerative diseases (e.g., Friedreich's ataxia (FRDA), Alzheimer's disease, and Parkinson's disease), stroke, and traumatic brain injury. Recently, we showed that lipophilic methylene blue (MB) and methylene violet (MV) analogues both promoted increased frataxin levels and mitochondrial biogenesis, in addition to their antioxidant activity in cultured FRDA cells. Presently, we report the synthesis of series of lipophilic phenothiazine analogues that potently inhibit ferroptosis. The most promising compounds (1b-5b) exhibited an improved protection compared to the parent phenothiazine against erastin- and RSL3-induced ferroptotic cell death. These analogues have equivalent or better potency than ferrostatin-1 (Fer-1) and liproxstatin-1 (Lip-1), that are among the most potent inhibitors of this regulated cell death described so far. They represent novel lead compounds with therapeutic potential in relevant ferroptosis-driven disease models such as FRDA.

NOVEL GLYCINE TRANSPORT INHIBITORS FOR THE TREATMENT OF PAIN

The present invention relates to novel glycine transport inhibitor compounds and their use for treating pain.

Modification of the side chain of micromolide, an anti-tuberculosis natural product

This paper describes a series of modifications of the side chain of micromolide, an anti-tuberculosis natural product. Most of the synthesized compounds showed significantly decreased activities, which suggests that the long aliphatic side chain of micromolide and its double bond are essential to its activity.

Total synthesis of anibamine, a novel natural product as a chemokine receptor CCR5 antagonist

The total synthesis of anibamine, the first and only natural product known as a chemokine receptor OCR5 antagonist, is reported herein. Anibamine was synthesized from acetylacetone and cyanoacetamide in 10 steps.

Studies on mimicry of naturally occurring annonaceous acetogenins: Non-THF analogues leading to remarkable selective cytotoxicity against human tumor cells

A class of structurally simplified analogues of the naturally occurring annonaceous acetogenins were developed, amongst which some non-THF analogues showed remarkable cytotoxicities against tumor cell lines, as well as good selectivity between human tumor cells and normal cells. The synthetic routes were significantly shortened because of the removal of the chiral centers bearing the THF rings on the natural templates. This simplification also provides access to the parallel synthesis of these mimics by a combinatorial strategy. The remaining stereogenic centers at the positions α to the ethereal links were introduced by the Chiron approach from the easily accessible chiral building blocks 6a and/or 6b, made in turn from L-ascorbic acid or Dmannitol, while the one in the butenolide segment was taken from L-lactate. All four diastereomeric non-THF analogues 2a-2d showed remarkable activity against the HCT-8 cell line, and better differentiation was found when testing against the HT-29 cell line. It was also discovered that both the butenolide and ethylene glycol subunits play essential roles in the cytotoxicities against tumor cell lines, while the 10-substituted hydroxy group and the absolute configuration of methyl group at the butenolide moiety are less important for their activity.

Diastereoselective synthesis of 2,5-disubstituted 3-hydroxypyrrolidine and 2,6-disubstituted 3-hydroxypiperidine derivatives by radical cyclisation; synthesis of (+)-bulgecinine and (-)-desoxoprosopinine

Cyclisation of the O-stannyl ketyl, generated from the aldehyde 17 by reaction with tributyltin hydride in the presence of AIBN, gives the 5-benzyloxymethyl-7-hydroxypyrrolooxazolidin-2-ones as a diastereoisomeric mixture of 7α-ol 18 and 7β-ol 19 (2:1), with high diastereoselectivity with respect to the 5,7a positions. (+)-Bulgecinine 8 is enantioselectively synthesised by stereospecific reduction of the ketone 20, derived from compounds 18 and 19. In a similar way, cyclisation of compound 40 gives a 2:1 mixture of compounds 41 and 42. Conversion of compound 41 into (-)-desoxoprosopinine 9 is successfully achieved.

Pheromone synthesis, CLXXIV: Synthesis of (5R,11S)-5,11-Dimethylheptadecane and (S)-2,5-Dimethylheptadecane, the major and the minor components of the sex pheromone of the geometrid moth, Lambdina fiscellaria lugubrosa

(5R,11S)-5,11-Dimethylheptadecane (1), the major component of the female-produced sex pheromone of the western hemlock looper (Lambdina fiscellaria lugubrosa), was synthesized by starting from the enantiomers of methyl 3-hydroxy-2-methylpropanoate (3). (S)-2,5-Dimethylheptadecane (2), the minor and synergistic component of the pheromone, was also synthesized by starting from (S)-citronellol (4). VCH Verlagsgesellschaft mbH, 1996.

Synthesis of Very Long Fatty Acid Methyl Esters

Phosphoranes, produced by treating alkyltriphenylphosphonium bromides with lithium hexamethyldisilazide, reacted with ω-oxo esters to give modest yields of the corresponding methyl cis-alkenoates.By an alternative method, treatment of ω-iodo esters with the complexes formed from reactions of alkylcopper(I) and Grignard reagents gave methyl alkanoates, cis-alkenoates, and methylene-interrupted cis,cis-alka-dienoates and cis,cis,cis-trienoates.The stereochemical integrity of the esters was determined by 13C NMR spectroscopy.

Amphiphilic Carbohydrate-Based Mesogens, VIII. A Facile Synthetic Route to Mesogenic L-ribo-1,2,3,4-Alkanetetrols

The Wittig olefinations of 2,3-O-isopropylidene-D-ribofuranose (1) with two equivalents of alkylidenetriphenylphosphorane (alkylidene: hexylidene-undecylidene) followed by hydrogenation catalyzed by palladium on carbon and subsequent deprotection yield (2R,3S,4S-("L-ribo")-1,2,3,4-alkanetetrols 5.These amphiphiles form the smectic A mesophase on melting.However, when 1 is heated with one equivalent of the alkylidenetriphenylphosphoranes for longer periods, (2R,3S,4R)-("D-lyxo")-1,2,3,4-alkanetetrol-type products 4 predominate.Key Words: Liquis crystals / Carbohydrates / L-ribo-, D-lyxo-1,2,3,4-Alkanetetrols / Wittig olefination

Pheromone Synthesis, CXXV. Synthesis of the Four Possible Stereoisomers of 3,7-Dimethylnonadecane, the Female Sex Pheromone of Agromyza frontella Rondani

The synthesis of the four possible stereoisomers of 3,7-dimethylnonadecane (1) has been achieved by starting from the enantiomers of methyl 3-hydroxy-2-methylpropanoate (2) and (R)-(+)-citronellic acid (3).