2657-44-5

Upstream product

• 782-28-5 4-(2-naphthyl)butyric acid 
• 785-19-3 methyl 4-(naphthalen-2-yl)butanoate 
• 109-99-9 tetrahydrofuran 
• 91-20-3 naphthalene 
• 1590-22-3 4-(2-naphthyl)-4-oxobutyric acid 
• 92587-69-4 4-(naphthalen-2-yl)but-3-yn-1-ol 
• 627-18-9 1-bromo-3-propanol 
• 2506-41-4 1-chloromethylnaphthalene 
• 2489-89-6 2-(3-buten-1-yl)-naphthalene 

Downstream Products

• 7475-48-1 δ-(Naphthyl-2)-valeriansaeure 

Relevant academic research and scientific papers

NOVEL COMPOUND HAVING AUXIN BIOSYNTHESIS INHIBITORY ACTIVITY, MANUFACTURING METHOD THEREFOR AND APPLICATION THEREOF

PROBLEM TO BE SOLVED: To provide a novel compound having an auxin biosynthesis inhibitory activity, and a novel compound having the auxin biosynthesis inhibitory activity with different mechanism of action from conventional auxin biosynthesis inhibitors. SOLUTION: An aspect of the invention relates to a compound represented by the formula (I), wherein n, Ar, A, X1, X2, R1, R2, R3, R4, R5, R6, R7, R8, and R9 have meaning described in the application and the Claims, or a salt thereof, or a solvate thereof. Another aspect of the invention relates to an auxin biosynthesis inhibitors containing the compound represented by the formula (I), or a salt thereof, or a solvate thereof as active ingredients, agricultural applications of the compound, and a manufacturing method of the compound. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT

Reductive coupling of benzyl oxalates with highly functionalized alkyl bromides by nickel catalysis

Coupling reactions involving non-sulfonated C-O electrophiles provide a promising method for forming C-C bonds, but the incorporation of functionalized or secondary alkyl groups remains a challenge due to the requirement for well-defined alkylmetal specie

Targeting an Aromatic Hotspot in Plasmodium falciparum 1-Deoxy-d-xylulose-5-phosphate Reductoisomerase with β-Arylpropyl Analogues of Fosmidomycin

Blocking the 2-C-methyl-d-erythrithol-4-phosphate pathway for isoprenoid biosynthesis offers new ways to inhibit the growth of Plasmodium spp. Fosmidomycin [(3-(N-hydroxyformamido)propyl)phosphonic acid, 1] and its acetyl homologue FR-900098 [(3-(N-hydroxyacetamido)propyl)phosphonic acid, 2] potently inhibit 1-deoxy-d-xylulose-5-phosphate reductoisomerase (Dxr), a key enzyme in this biosynthetic pathway. Arylpropyl substituents were introduced at the β-position of the hydroxamate analogue of 2 to study changes in lipophilicity, as well as electronic and steric properties. The potency of several new compounds on the P. falciparum enzyme approaches that of 1 and 2. Activities against the enzyme and parasite correlate well, supporting the mode of action. Seven X-ray structures show that all of the new arylpropyl substituents displace a key tryptophan residue of the active-site flap, which had made favorable interactions with 1 and 2. Plasticity of the flap allows substituents to be accommodated in many ways; in most cases, the flap is largely disordered. Compounds can be separated into two classes based on whether the substituent on the aromatic ring is at the meta or para position. Generally, meta-substituted compounds are better inhibitors, and in both classes, smaller size is linked to better potency.

Benzoxazolone Carboxamides as Potent Acid Ceramidase Inhibitors: Synthesis and Structure-Activity Relationship (SAR) Studies

Ceramides are lipid-derived intracellular messengers involved in the control of senescence, inflammation, and apoptosis. The cysteine amidase, acid ceramidase (AC), hydrolyzes these substances into sphingosine and fatty acid and, by doing so, regulates their signaling activity. AC inhibitors may be useful in the treatment of pathological conditions, such as cancer, in which ceramide levels are abnormally reduced. Here, we present a systematic SAR investigation of the benzoxazolone carboxamides, a recently described class of AC inhibitors that display high potency and systemic activity in mice. We examined a diverse series of substitutions on both benzoxazolone ring and carboxamide side chain. Several modifications enhanced potency and stability, and one key compound with a balanced activity-stability profile (14) was found to inhibit AC activity in mouse lungs and cerebral cortex after systemic administration. The results expand our arsenal of AC inhibitors, thereby facilitating the use of these compounds as pharmacological tools and their potential development as drug leads.

BENZOXAZOLONE DERIVATIVES AS ACID CERAMIDASE INHIBITORS, AND THEIR USE AS MEDICAMENTS

The present invention relates to benzoxazolone derivatives as acid ceramidase inhibitors, pharmaceutical compositions containing these inhibitors and methods of inhibiting acid ceramidase for the treatment of disorders in which modulation of the levels of ceramide is clinically relevant. The invention also provides benzoxazolone derivatives for use as a medicament in the treatment of cancer, inflammation, pain, inflammatory pain or pulmonary diseases.

On the mechanism of arene-catalyzed lithiation: The role of arene dianions - Naphthalene radical anion versus naphthalene dianion

The use of lithium and a catalytic amount of an arene is a well-established methodology for the preparation of organolithium reagents that manifest greater reactivity than the classical lithium-arene solutions. In order to rationalize this conduct, the participation of a highly reduced species, the dianion, is proposed and its reactivity explored. Studies of kinetics and of distribution of products reveal that the electron-transfer (ET) reactivity profile of dilithium naphthalenide in its reaction with organic chlorides excludes alternative mechanisms of halogen- lithium exchange. The process generates organolithium compounds. The dianion thus emerges along with the radical anion as a suitable candidate for catalytic cycles in certain processes. Endowed with a higher redox potential than its radical anion counterpart, dilithium naphthalene displays a broader spectrum of reactivity and so increases the range of substrates suitable for lithiation. The reaction of dilithium naphthalene with THF is one example of the divergent reactivity of the radical anion and the dianion, which has been the source of apparent misinterpretation of results in the past and has now been appropriately addressed.

Probing the abilities of synthetically useful serine proteases to discriminate remote stereocenters. Chiral naphthyl aldehyde inhibitors

The capacities of subtilisin Carlsberg (SC) and α-chymotrypsin (CT), which are representative of synthetically useful serine proteases, to discriminate between R- and S-configurations of stereocenters remote from the catalytic site have been further explo

Photolyses of (3-Naphthoxypropyl)-, (4-Naphthylbutyl)-, and (4-Naphthyl-4-oxobutyl)cobaloxime

The cobalt-carbon bond of the titled compounds is photochemically cleaved to generate an organoradical and a cobaloxime(II) radical pair. 3-(1- or 2-naphtoxy)propyl, 4-(1- or 2-naphthyl)butyl, and 4-(1-or 2-napthyl)-4-oxobutyl radicals thus formed undergo three types of reactions: (a) hydrogen abstraction to give a saturated terminal, (b) hydrogen elimination to give a terminal olefin, and (c) substitution on the naphthalene ring.In benzene and radicals follow process b exclusively (the radicals from (3-(2-napthoxy)propyl)cobaloxime (1a), (3-(1-napthoxy)propyl)cobaloxime (2a), and (4-(1-napthyl)butyl)cobaloxime (2 b)) or preferentially (the radicals from (4-(2-napthyl)butyl)cobaloxime (1 b), (4-(2-napthyl)-4-oxobutyl)cobaloxime (1c), and 4-(1-napthyl)-4-oxobutyl)cobaloxime (2c)).In chloroform, process a becomes important to the extent as the sum of the other two processes.In water-acetonitril (4:1), process c becomes important and even takes precedence of others for the radicals from 1b and 1c.This feature is accounted for by the folding of the side chain of hydrophobic radicals.Encapsulation of the radicals in β-cyclodextrin stimulates process c except for the case of the radical from 2c.In the case of cobaloxime 2c, α-cyclodextrin does not effect the partition process of the intermediate radical.This feature is accounted for by the shallow inclusion of the radical due to the hydrogen bonding as depicted in Figure 1d.

Electrophilic Substitution in Naphthalenes: Cyclisation of Naphthylbutanols to Tetrahydrophenanthrene

Both 4-(1-naphthyl)butanol and 4-(2-naphthyl)butanol cyclised in refluxing boron trifluoride-ether to give 1,2,3,4-tetrahydrophenanthrene.By use of the corresponding 1,1-dideuteriobutanol derivatives and analysis of the products by 220 MHz 1H n.m.r. spectroscopy it has been demonstrated that the 1-naphthylbutanol cyclises by two distinct pathways, (a) by direct attack (84percent) at the 2-position, and (b) by ipso-attack (16percent) at the 1-position of the naphthalene nucleus, followed by rearrangement.The 2-naphthylbutanol cyclises exclusively by direct substitution at the 1-position.With 4-(4-methoxy-1-naphthyl)-1,1-dideuteriobutanol on the other hand the proportion of ipso-substitution rises to 71 percent as shown by the 360 MHz 1H n.m.r. spectra of the resulting mixture of tetrahydrophenanthrenes.