(1R,2R)-N-([S]-1-{4-[5-broMo-2-oxo-2,3-dihydro-1H-benzo(d)iMidazol-1-yl]piperidin-1-yl}propan-2-yl)-2-phenylcyclopropanecarboxaMide

Product Name: (1R,2R)-N-([S]-1-{4-[5-broMo-2-oxo-2,3-dihydro-1H-benzo(d)iMidazol-1-yl]piperidin-1-yl}propan-2-yl)-2-phenylcyclopropanecarboxaMide
CAS No.: 1246303-14-9
Chemical Name: (1R,2R)-N-([S]-1-{4-[5-broMo-2-oxo-2,3-dihydro-1H-benzo(d)iMidazol-1-yl]piperidin-1-yl}propan-2-yl)-2-phenylcyclopropanecarboxaMide
Synonyms: ML270;VU0359595;(1R,2R)-N-[(2S)-1-[4-(5-bromo-2-oxo-3H-benzimidazol-1-yl)piperidin-1-yl]propan-2-yl]-2-phenylcyclopropane-1-carboxamide;(1R,2R)-N-([S]-1-{4-[5-broMo-2-oxo-2,3-dihydro-1H-benzo(d)iMidazol-1-yl]piperidin-1-yl}propan-2-yl)-2-phenylcyclopropanecarboxaMide;Cyclopropanecarboxamide, N-[(1S)-2-[4-(5-bromo-2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinyl]-1-methylethyl]-2-phenyl-, (1R,2R)-;(1R,2R)-N-([S]-1-{4-[5-BROMO-2-OXO-2,3-DIHYDRO-1H-BENZO(D)IMIDAZOL-1-YL]PIPERIDIN-1-YL}PROPAN-2-YL)-2-PHENYLCYCLOPROPANECARBOXAMIDE;VU0359595
CBNumber: CB52719857
Molecular Formula: C25H29BrN4O2
Formula Weight: 497.43
MOL File: 1246303-14-9.mol

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(1R,2R)-N-([S]-1-{4-[5-broMo-2-oxo-2,3-dihydro-1H-benzo(d)iMidazol-1-yl]piperidin-1-yl}propan-2-yl)-2-phenylcyclopropanecarboxaMide Property

Density: 1.395±0.06 g/cm3(Predicted)
storage temp.: 2-8°C
solubility: DMSO: soluble5mg/mL, clear
pka: 11.11±0.30(Predicted)
form: powder
color: white to beige

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Safety

WGK Germany: 3

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Cayman Chemical

Product number: 10955
Product name: VU0359595
Purity: ≥95%
Packaging: 1mg
Price: $40
Updated: 2024/03/01

Cayman Chemical

Product number: 10955
Product name: VU0359595
Purity: ≥95%
Packaging: 5mg
Price: $139
Updated: 2024/03/01

Cayman Chemical

Product number: 10955
Product name: VU0359595
Purity: ≥95%
Packaging: 10mg
Price: $236
Updated: 2024/03/01

Cayman Chemical

Product number: 10955
Product name: VU0359595
Purity: ≥95%
Packaging: 25mg
Price: $541
Updated: 2024/03/01

TRC

Product number: V787565
Product name: VU0359595
Packaging: 10mg
Price: $150
Updated: 2021/12/16

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(1R,2R)-N-([S]-1-{4-[5-broMo-2-oxo-2,3-dihydro-1H-benzo(d)iMidazol-1-yl]piperidin-1-yl}propan-2-yl)-2-phenylcyclopropanecarboxaMide Chemical Properties,Usage,Production

Uses

VU0359595 is an inhibitor of phospholipase D1 (PLD1) which is more than 1700 fold selective over phospholipase D2 (PLD2). This complex only binds and inhibit phospholipase D though an allosteric site, but it noes not interact with the catalytic site of phospholipase D.

Biological Activity

vu0359595 is a potent and selective inhibitor of pld1.phospholipase d (pld) isozymes mediate phospholipid hydrolysis and transphosphatidylation. until now, two mammalian isoforms of pld, pld1, and pld2, have been identified. it has been identified that pld has been implicated in a human cancer cell progression, actin cytoskeleton reorganization and cell motility [1].

in vitro

vu0359595 was an inhibitor of pld1 with an ic50 of 3.7 nm. vu0359595 showed >1,700-fold selectivity over pld2. the ic50 of was vu0359595 against pld2 was 6.4 μm [1]. preliminary evidence has demonstrated that vu0359595 showed no interaction with the catalytic site of pld, but may bind and inhibit pld through an allosteric site [1]. at 500 nm, vu0359595 significantly reduced the pld activity in astroglial cultures from wild-type mice by 58% [2]. in cells stimulated by 1% fcs, vu0359595 decreased cell proliferation in wild-type and pld2-deficient cells at a concentration of 500 nm [2]. vu0359595 (500 nm) significantly reduced cell growth in cells stimulated by either mitogen [2].

References

[1] lewis j a, scott s a, lavieri r, et al. design and synthesis of isoform-selective phospholipase d (pld) inhibitors. part i: impact of alternative halogenated privileged structures for pld1 specificity[j]. bioorganic & medicinal chemistry letters, 2009, 19(7): 1916-1920.
[2] burkhardt u, beyer s, klein j. role of phospholipases d1 and 2 in astroglial proliferation: effects of specific inhibitors and genetic deletion[j]. european journal of pharmacology, 2015, 761: 398-404.

(1R,2R)-N-([S]-1-{4-[5-broMo-2-oxo-2,3-dihydro-1H-benzo(d)iMidazol-1-yl]piperidin-1-yl}propan-2-yl)-2-phenylcyclopropanecarboxaMide Preparation Products And Raw materials

Raw materials

Preparation Products

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1246303-14-9, (1R,2R)-N-([S]-1-{4-[5-broMo-2-oxo-2,3-dihydro-1H-benzo(d)iMidazol-1-yl]piperidin-1-yl}propan-2-yl)-2-phenylcyclopropanecarboxaMideRelated Search:

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(1R,2R)-N-([S]-1-{4-[5-broMo-2-oxo-2,3-dihydro-1H-benzo(d)iMidazol-1-yl]piperidin-1-yl}propan-2-yl)-2-phenylcyclopropanecarboxaMide

VU0359595

(1R,2R)-N-([S]-1-{4-[5-BROMO-2-OXO-2,3-DIHYDRO-1H-BENZO(D)IMIDAZOL-1-YL]PIPERIDIN-1-YL}PROPAN-2-YL)-2-PHENYLCYCLOPROPANECARBOXAMIDE;VU0359595

(1R,2R)-N-[(2S)-1-[4-(5-bromo-2-oxo-3H-benzimidazol-1-yl)piperidin-1-yl]propan-2-yl]-2-phenylcyclopropane-1-carboxamide

Cyclopropanecarboxamide, N-[(1S)-2-[4-(5-bromo-2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinyl]-1-methylethyl]-2-phenyl-, (1R,2R)-

ML270

1246303-14-9

C25H29BrN4O2