J147
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MedKoo CAT#: 522384

CAS#: 1146963-51-0 (E/Z isomers)

Description: J147 is a potent neuroprotective and neurotrophic compound. J147 protects against neurotoxicity in cortical neurons in vitro (EC50 = 25 - 200 nM). J147. J147 reverses cognitive impairment in aged Alzheimer's disease mice. J147 is an exciting new compound that is extremely potent, safe in animal studies and orally active. J147 is a potential AD therapeutic due to its ability to provide immediate cognition benefits, and it also has the potential to halt and perhaps reverse disease progression in symptomatic animals as demonstrated in these studies.

Chemical Structure

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J147
CAS# 1146963-51-0 (E/Z isomers)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 522384
Name: J147
CAS#: 1146963-51-0 (E/Z isomers)
Chemical Formula: C18H17F3N2O2
Exact Mass: 350.12
Molecular Weight: 350.340
Elemental Analysis: C, 61.71; H, 4.89; F, 16.27; N, 8.00; O, 9.13

Price and Availability

Size Price Availability Quantity
10mg USD 110 Ready to ship
25mg USD 225 Ready to ship
50mg USD 385 Ready to ship
100mg USD 685 Ready to ship
200mg USD 1250 Ready to ship
500mg USD 2650 Ready to ship
1g USD 3650 Ready to ship
2g USD 5950 Ready to ship
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Related CAS #: 1417911-00-2 (C13-labeled)   1146963-51-0 (E/Z isomers)   1807913-16-1 (E-isomer)    

Synonym: J147; J 147; J-147.

IUPAC/Chemical Name: 2,2,2-Trifluoroacetic acid 1-(2,4-Dimethylphenyl)-2-[(3-methoxyphenyl)methylene]hydrazide

InChi Key: HYMZAYGFKNNHDN-SSDVNMTOSA-N

InChi Code: InChI=1S/C18H17F3N2O2/c1-12-7-8-16(13(2)9-12)23(17(24)18(19,20)21)22-11-14-5-4-6-15(10-14)25-3/h4-11H,1-3H3/b22-11+

SMILES Code: O=C(N(C1=CC=C(C)C=C1C)/N=C/C2=CC=CC(OC)=C2)C(F)(F)F

Appearance: Light yellow solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target: J-147 is a neuroprotective agent for cognitive enhancement that inhibits monoamine oxidase B (MAO B) and the dopamine transporter with EC50 values of 1.88 μM and 0.649 μM, respectively.
In vitro activity: Additional support for an effect of J147 on neurotrophic pathways came from a study with HT22 cells. HT22 is a nerve cell line derived from mouse brain and is widely used to study nerve cell physiology. To examine the effect of J147 on gene expression, a DNA microarray study probed expression of over 34,000 named mouse genes. J147 increased transcription factor Egr3 mRNA expression 8-fold following one hour of treatment, while Ngf mRNA was up-regulated 2.8-fold (Table1). Also up-regulated was mRNA from another member of the Egr family, Egr1, with a 2.5-fold increase and mRNA from a member of the Spred family, Spred2, with a 2.7-fold increase. J147 did have an effect on other genes. To determine the biological consequences of J147 induction of neurotrophin expression, it was asked if conditioned media (CM) prepared from HT22 cells treated with J147 could stimulate neurite outgrowth in PC12 cells. Both conditioned medium from J147 treated cells (Figure3G,3G, middle right panel) and NGF treated cells promoted neurite outgrowth (Figure3G,3G, top right panel), while control medium did not (Figure3G,3G, top and middle left panels). This effect was reduced by anti-NGF anti-sera suggesting that J147 releases neurotrophins with an effect on neurites similar to those released by NGF (Figure3G,3G, bottom panels). Reference: Alzheimers Res Ther. 2013; 5(3): 25. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3706879/
In vivo activity: Both male and female huAPP/PS1 mice were aged to 20 months. At this time, the mice were randomly assigned to one of two groups: 11 mice were fed normal food and 13 mice were fed the same diet but also containing 200 ppm J147. Following three months of treatment, all mice were analyzed for spatial memory performance by the two-day water maze (Figure1A), disinhibition phenotype by the elevated plus maze (Figure1B), and contextual and cued memory by a fear conditioning assay (Figure1C and 1D, respectively). Results from Day 1 indicate no defects in AD or AD + J147 in the ability to swim or see as both have similar escape latency. Results from this two-day water maze show that AD mice take considerably longer to find the hidden platform on Day 2 than AD mice treated with J147 for three months (Figure1A), demonstrating that J147 significantly improved the spatial navigational memory in aged, transgenic AD mice. The data demonstratse that aged transgenic AD mice do indeed spend more time in the open arm, a phenotype that was completely rescued by treatment with J147 for three months (Figure1B). AD mice alone spent significantly less time freezing in response to the context associated with the aversive stimulus in our experiment, indicating that they did not remember the context, a phenotype that was rescued by treatment with J147 (Figure1C). Results from these behavioral assays show that J147 has the ability to rescue the cognitive decline and disinhibition phenotype associated with AD when administered at an extremely late stage in the disease progression when pathology is already far advanced. Reference: Alzheimers Res Ther. 2013; 5(3): 25. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3706879/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 68.0 194.10

Preparing Stock Solutions

The following data is based on the product molecular weight 350.34 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Prior M, Dargusch R, Ehren JL, Chiruta C, Schubert D. The neurotrophic compound J147 reverses cognitive impairment in aged Alzheimer's disease mice. Alzheimers Res Ther. 2013 May 14;5(3):25. doi: 10.1186/alzrt179. PMID: 23673233; PMCID: PMC3706879. 2. Currais A, Huang L, Goldberg J, Petrascheck M, Ates G, Pinto-Duarte A, Shokhirev MN, Schubert D, Maher P. Elevating acetylCoA levels reduces aspects of brain aging. Elife. 2019 Nov 19;8:e47866. doi: 10.7554/eLife.47866. PMID: 31742554; PMCID: PMC6882557.
In vitro protocol: 1. Prior M, Dargusch R, Ehren JL, Chiruta C, Schubert D. The neurotrophic compound J147 reverses cognitive impairment in aged Alzheimer's disease mice. Alzheimers Res Ther. 2013 May 14;5(3):25. doi: 10.1186/alzrt179. PMID: 23673233; PMCID: PMC3706879.
In vivo protocol: 1. Prior M, Dargusch R, Ehren JL, Chiruta C, Schubert D. The neurotrophic compound J147 reverses cognitive impairment in aged Alzheimer's disease mice. Alzheimers Res Ther. 2013 May 14;5(3):25. doi: 10.1186/alzrt179. PMID: 23673233; PMCID: PMC3706879. 2. Currais A, Huang L, Goldberg J, Petrascheck M, Ates G, Pinto-Duarte A, Shokhirev MN, Schubert D, Maher P. Elevating acetylCoA levels reduces aspects of brain aging. Elife. 2019 Nov 19;8:e47866. doi: 10.7554/eLife.47866. PMID: 31742554; PMCID: PMC6882557.

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1: Kim K, Park KS, Kim MK, Choo H, Chong Y. Dicyanovinyl-substituted J147 analogue inhibits oligomerization and fibrillation of β-amyloid peptides and protects neuronal cells from β-amyloid-induced cytotoxicity. Org Biomol Chem. 2015 Aug 25. [Epub ahead of print] PubMed PMID: 26303522.

2: Chen HY, Xu DP, Tan GL, Cai W, Zhang GX, Cui W, Wang JZ, Long C, Sun YW, Yu P, Tsim KW, Zhang ZJ, Han YF, Wang YQ. A Potent Multi-functional Neuroprotective Derivative of Tetramethylpyrazine. J Mol Neurosci. 2015 Aug;56(4):977-87. doi: 10.1007/s12031-015-0566-x. Epub 2015 May 17. PubMed PMID: 25982925.

3: Prior M, Dargusch R, Ehren JL, Chiruta C, Schubert D. The neurotrophic compound J147 reverses cognitive impairment in aged Alzheimer's disease mice. Alzheimers Res Ther. 2013 May 14;5(3):25. doi: 10.1186/alzrt179. eCollection 2013. PubMed PMID: 23673233; PubMed Central PMCID: PMC3706879.

4: Chiruta C, Zhao Y, Tang F, Wang T, Schubert D. Metabolism of a potent neuroprotective hydrazide. Bioorg Med Chem. 2013 May 15;21(10):2733-41. doi: 10.1016/j.bmc.2013.03.020. Epub 2013 Mar 24. PubMed PMID: 23582448.

5: Wang M, Gao M, Zheng QH. The first synthesis of [11C]J147, a new potential PET agent for imaging of Alzheimer's disease. Bioorg Med Chem Lett. 2013 Jan 15;23(2):524-7. doi: 10.1016/j.bmcl.2012.11.031. Epub 2012 Nov 22. PubMed PMID: 23237833.

6: Magro M, van Geuns RJ. TheTryton side branch stent. EuroIntervention. 2010 Dec;6 Suppl J:J147-50. doi: 10.4244/EIJV6SUPJA25. PubMed PMID: 21930481.

7: Ishii R, Horie M. [Principles of PCR technologies]. Shokuhin Eiseigaku Zasshi. 2001 Apr;42(2):J147-51. Japanese. PubMed PMID: 11486392.