2854-16-2Relevant articles and documents
Total synthesis of hydroxy-α- and hydroxy-β-sanshool using Suzuki-Miyaura coupling
Igarashi, Yasushi,Aoki, Katsuyuki,Nishimura, Hiroaki,Morishita, Isao,Usui, Kimitoshi
, p. 1088 - 1091 (2012)
Here, we describe the first total synthesis of hydroxyl-α- and hydroxyl-β-sanshool, which involves Suzuki-Miyaura coupling (SMC). Hydroxy-α-sanshool (1) was synthesized by SMC of bromoalkyne 4 with boronate 3 followed by (Z)-selective reduction of the triple bond in the coupling product. Hydroxy-β-sanshool (2) was synthesized by regio- and (E)-selective conversion of 4 to iodoalkene 11 followed by SMC with 3.
BICYCLIC PHOSPHANES. PART 2. SPONTANEOUS DIMERIZATION OF A CONSTRAINED BICYCLIC PHOSPHANE. THE CRYSTAL AND MOLECULAR STRUCTURE OF A TRICYCLIC COMPOUND CONTAINING THE DIOXADIAZADIPHOSPHECINE RING
Bonningue, Corine,Houalla, Douraid,Wolf, Robert,Jaud, Joel
, p. 773 - 776 (1983)
The dimerization of 3,3,7,7-tetramethyl-2,8-dioxa-5-aza-1-phosphaIIIbicyclooctane (1) leads to octahydro-2,2,6,6,10,10,14,14-octamehylbis-1,2,3-oxazaphospholo-1,6,3,8,2,7-dioxadiazadiphosphecine (2), a tricyclic compound with sixteen atoms around the periphery.The preparation, identification, and the X-ray structure are described.A pathway for the formation of the dimer is suggested by the trans-position of the two phosphorus ione pairs.
Synthesis and evaluation of new alkylamides derived from α-hydroxysanshool, the pungent molecule in szechuan pepper
Menozzi, Candice,Riera, Celine E.,Munari, Caroline,Coutre, Johannes Le,Robert, Fabien
, p. 1982 - 1989 (2009)
Szechuan pepper is widely used in Asia as a spice for its pleasant pungent and tingling sensations, produced by natural alkylamides called sanshools. R-Hydroxysanshool, the main alkylamide found in the pericarp of the fruit, stimulates sensory neurons innervating the mouth by targeting two chemosensitive members of the transient receptor potential (TRP) channels, TRPV1 and TRPA1. As it was previously found that configuration of the unsaturations in the R-hydroxysanshool alkyl chain is required for TRPA1 but not TRPV1 selectivity, this study aimed at obtaining more potent and selective TRPA1 agonists using R-hydroxysanshool as a starting material. This paper reports the preparation of new alkylamides derived from sanshool and their efficacy in stimulating TRPA1 and TRPV1 receptors. The data provide knowledge of the main sanshool chemical functionalities required for TRP channel activation, but they also evidence new selective and potent TRPA1 agonists based on α-hydroxysanshool.
IMIDAZOQUINOLINE-TYPE COMPOUNDS AND USES THEREOF
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Paragraph 0010; 0083; 0088, (2021/10/11)
Provided in the present disclosure are imidazoquinoline-type compounds, methods for their preparation, pharmaceutical compositions thereof and their use, wherein the imidazoquinoline-type compounds, upon local administration, form depots inducing cell mediated immune response while mitigating a systemic proinflammatory immune response.
LOCALLY ACTING TOLL-LIKE RECEPTOR 7 (TLR7) AND/OR TLR8 AGONIST IMMUNOTHERAPY COMPOUNDS AND THEIR USES
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Paragraph 0029; 00163-00164; 00169, (2020/10/19)
Provided in the present disclosure are immunotherapy compounds, pharmaceutical compositions thereof and their use, wherein the immunotherapy compounds, upon local administration, form depots inducing cell mediated immune response while mitigating a systemic proinflammatory immune response.
Intermediate compound used for synthesizing valnemulin hydrochloride, and preparation method of valnemulin hydrochloride
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Paragraph 0018; 0019; 0023, (2017/08/02)
The invention discloses an intermediate compound used for synthesizing valnemulin hydrochloride. The chemical structure of the intermediate compound used for synthesizing valnemulin hydrochloride is represented by a formula in the invention. A preparation method of the intermediate compound comprises following steps: beta-hydroxyisovaleric acid is subjected to Curtius rearrangement reaction so as to obtain 2-methyl-2-hydroxy propylamine; 2-methyl-2-hydroxy propylamine and D-valine Dane salt are subjected to mixed anhydride method reaction so as to obtain an amide product; the amide product is subjected to hydroxy activation under alkaline conditions with methylsulfonyl chloride, and then is reacted with potassium thioacetate. The preparation method of valnemulin hydrochloride comprises following steps: pleuromutilin is reacted with paratoluensulfonyl chloride so as to obtain pleuromutilin p-tosylate; pleuromutilin p-tosylate is reacted with the intermediate compound, and hydrochloric acid deprotection is carried out so as to obtain valnemulin hydrochloride. In the preparation method of valnemulin hydrochloride, no dimethyl cysteamine hydrochloride is needed, production conditions are mild, no environment pollution is caused, and the preparation method is suitable for industrialized production.
Remote C(sp3)-H Oxygenation of Protonated Aliphatic Amines with Potassium Persulfate
Lee, Melissa,Sanford, Melanie S.
supporting information, p. 572 - 575 (2017/02/10)
This letter describes the development of a method for selective remote C(sp3)-H oxygenation of protonated aliphatic amines using aqueous potassium persulfate. Protonation serves to deactivate the proximal C(sp3)-H bonds of the amine substrates and also renders the amines soluble in the aqueous medium. These reactions proceed under relatively mild conditions (within 2 h at 80 °C with amine as limiting reagent) and do not require a transition metal catalyst. This method is applicable to a variety of types of C(sp3)-H bonds, including 3°, 2°, and benzylic C-H sites in primary, secondary, and tertiary amine substrates.
INDANYLOXYPHENYLCYCLOPROPANECARBOXYLIC ACIDS
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Paragraph 0427-0428, (2015/06/03)
A compound of formula I, wherein the groups R1, R2, R3, X, m, and n are defined as in claim 1, which have valuable pharmacological properties, in particular bind to the GPR40 receptor and modulate its activity. The compounds are suitable for treatment and prevention of diseases which can be influenced by this receptor, such as metabolic diseases, in particular diabetes type 2. Furthermore, the invention relates to novel intermediates, useful for the synthesis of compounds of formula I.
NEW INDANYLOXYPHENYLCYCLOPROPANECARBOXYLIC ACIDS
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Page/Page column 71; 72, (2015/06/11)
The present invention relates to compounds of general formula (I), wherein the groups R1, R2, R3, X, m and n are defined as in claim 1, wich have valuable pharmacological properties, in particular bind to the GPR40 receptor and modulate its activity. The compounds are suitable for treatment and prevention of diseases which can be influenced by this receptor, such as metabolic diseases, in particular diabetes type 2. Furthermore, the invention relates to novel intermediates, useful for the synthesis of compounds of formula I.
IMMUNOMODULATORY CONJUGATES
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Page/Page column 77, (2013/05/23)
The present invention provides an immunomodulatory compound comprising a carbohydrate polymer comprising mannose, wherein the carbohydrate polymer is conjugated to at least one immune modulator. The present invention also provides for the use of this compound in immunomodulatory compositions for vaccination and gene therapy methods, together with processes for its preparation.
