56396-35-1 Usage
Description
2-cyano-3-(1-phenylindol-3-yl)acrylate is an organic compound with a molecular formula of C17H11NO2 and a molecular weight of 261.28 g/mol. It is characterized by its cyano group (CN) attached to a 3-(1-phenylindol-3-yl)acrylate moiety, which consists of a phenylindole core with a vinyl group (C=C) attached to the 3-position. This molecule is known for its unique chemical properties and potential applications in various fields.
Uses
Used in Pharmaceutical Industry:
2-cyano-3-(1-phenylindol-3-yl)acrylate is used as an intermediate compound for the synthesis of various pharmaceuticals. Its unique structure allows it to be a key component in the development of new drugs with potential therapeutic applications.
Used in Chemical Research:
In the field of chemical research, 2-cyano-3-(1-phenylindol-3-yl)acrylate serves as a valuable starting material for the synthesis of a wide range of organic compounds. Its reactivity and structural features make it an attractive candidate for further functionalization and exploration of novel chemical reactions.
Used in Dye and Pigment Industry:
Due to its distinct chemical structure, 2-cyano-3-(1-phenylindol-3-yl)acrylate can be used as a building block for the development of new dyes and pigments. Its potential to form various chromophores and its ability to absorb and emit light make it a promising candidate for the creation of novel colorants.
Used in Material Science:
The unique properties of 2-cyano-3-(1-phenylindol-3-yl)acrylate can be exploited in the development of advanced materials with specific optical, electronic, or mechanical properties. Its incorporation into polymers or other materials can lead to the creation of new materials with tailored characteristics for various applications.
Used in Analytical Chemistry:
2-cyano-3-(1-phenylindol-3-yl)acrylate can be employed as a reagent or a reference compound in analytical chemistry. Its distinct chemical and physical properties make it suitable for use in various analytical techniques, such as chromatography, spectroscopy, or electrochemistry, to study and characterize other compounds.
Biochem/physiol Actions
UK-5099 induces lactate generation.
References
1) Shearman and Halestrap (1984), The concentration of the mitochondrial pyruvate carrier in rat liver and heart mitochondria determined with alpha-cyano-beta-(1-phenylindol-3-yl)acrylate; Biochem. J.,?223?673
2) Divakaruni?et al.?(2013),?Thiazolidinediones are acute, specific inhibitors of the mitochondrial pyruvate carrier.; Proc. Natl. Acad. Sci. USA,?110?5422
3) Zhong?et al. (2015),?Application of mitochondrial pyruvate carrier blocker UK5099 creates metabolic reprogram and greater stem-like properties in LnCap prostate cancer cells in vitro; Oncotarget,?6?37758
4) Jourdain?et al. (2016),?L-Lactate protects neurons against excitotoxicity: implication of an ATP-mediated signaling cascade; Sci. Rep.,?6?21250
5) Wiemer?et al.?(1995),?The inhibition of pyruvate transport across the plasma membrane of the bloodstream form of Trypanosoma brucei and its metabolic implications; Biochem. J.,?312?479
Check Digit Verification of cas no
The CAS Registry Mumber 56396-35-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,6,3,9 and 6 respectively; the second part has 2 digits, 3 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 56396-35:
(7*5)+(6*6)+(5*3)+(4*9)+(3*6)+(2*3)+(1*5)=151
151 % 10 = 1
So 56396-35-1 is a valid CAS Registry Number.
InChI:InChI=1/C18H12N2O2/c19-11-13(18(21)22)10-14-12-20(15-6-2-1-3-7-15)17-9-5-4-8-16(14)17/h1-10,12H,(H,21,22)/b13-10+
56396-35-1Relevant articles and documents
Development of Novel Mitochondrial Pyruvate Carrier Inhibitors to Treat Hair Loss
Liu, Xiaoguang,Flores, Aimee A.,Situ, Lisa,Gu, Wen,Ding, Hui,Christofk, Heather R.,Lowry, William E.,Jung, Michael E.
, p. 2046 - 2063 (2021/02/16)
Herein, we report the synthesis and evaluation of novel analogues of UK-5099 both in vitro and in vivo for the development of mitochondrial pyruvate carrier (MPC) inhibitors to treat hair loss. A comprehensive understanding of the structure-activity relationship was obtained by varying four positions of the hit compound, namely, the alkyl group on the N1 position, substituents on the indole core, various aromatic and heteroaromatic core structures, and various Michael acceptors. The major discovery was that the inhibitors with a 3,5-bis(trifluoromethyl)benzyl group at the N1 position were shown to have much better activity than JXL001 (UK-5099) to increase cellular lactate production. Additionally, analogue JXL069, possessing a 7-azaindole heterocycle, was also shown to have significant MPC inhibition activity, which further increases the chemical space for drug design. Finally, more than 10 analogues were tested on shaved mice by topical treatment and promoted obvious hair growth on mice.
COMPOSITIONS AND METHODS FOR MODULATING HAIR GROWTH
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Page/Page column 45, (2019/01/17)
The present disclosure relates to compounds that are capable of inhibiting the mitochondrial pyruvate carrier and promoting hair growth. The disclosure further relates to methods of promoting hair growth or treating conditions or disorders affecting hair growth, such as baldness or alopecia.
