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[ CAS No. 103-67-3 ] {[proInfo.proName]}

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Chemical Structure| 103-67-3
Chemical Structure| 103-67-3
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Quality Control of [ 103-67-3 ]

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Product Citations

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Mokhtarpour, Nazanin ; Sterling, Alyssa ; Garcia, Joshua J. , et al. DOI: PubMed ID:

Abstract: Reactive oxygen species (ROS) are a heterogeneous group of highly reactive ions and mols. derived from mol. oxygen (O2) which can cause DNA damage and lead to skin cancer. NADPH oxidase 1 (Nox1) is a major producer of ROS in the skin upon exposure to UV light. Functionally, Nox1 forms a holoenzyme complex that generates two superoxide mols. and reduces NADPH. The signaling activation occurs when the organizer subunit Noxo1 translocates to the plasma membrane bringing a cytochrome P 450, through interaction with Cyba. We propose to design inhibitors that prevent Cyba-Noxo1 binding as a topical application to reduce UV-generated ROS in human skin cells. Design started from an apocynin backbone structure to generate a small mol. to serve as an anchor point. The initial compound was then modified by addition of a polyethylene glycol linked biotin. Both inhibitors were found to be non-toxic in human keratinocyte cells. Further in vitro experiments using isothermal calorimetric binding quantification showed the modified biotinylated compound bound Noxo1 peptide with a KD of 2 nM. Both using isothermal calorimetric binding and MALDI (TOF) MS showed that binding of a Cyba peptide to Noxo1 was blocked. In vivo experiments were performed using donated skin explants with topical application of the two inhibitors. Experiments show that UV light exposure of with the lead compound was able to reduce the amount of cyclobutene pyrimidine dimers in DNA, a mol. known to lead to carcinogenesis. Further synthesis showed that the polyethylene glycol but not the biotin was essential for inhibition.

Keywords: Reactive oxygen species ; Apocynin ; UV ; Noxo1 ; Cyba ; Cyclobutane pyrimidine dimer ; CPD ; UV protection

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Hegde, Pooja V. ; Aragaw, Wassihun W. ; Cole, Malcolm S. , et al. DOI: PubMed ID:

Abstract: Tuberculosis (TB) remains a leading cause of infectious disease-related mortality and morbidity. Pyrazinamide (PZA) is a critical component of the first-line TB treatment regimen because of its sterilizing activity against non-replicating Mycobacterium tuberculosis (Mtb), but its mechanism of action has remained enigmatic. PZA is a prodrug converted by pyrazinamidase encoded by pncA within Mtb to the active moiety, pyrazinoic acid (POA) and PZA resistance is caused by loss-of-function mutations to pyrazinamidase. We have recently shown that POA induces targeted protein degradation of the enzyme PanD, a crucial component of the CoA biosynthetic pathway essential in Mtb. Based on the newly identified mechanism of action of POA, along with the crystal structure of PanD bound to POA, we designed several POA analogs using structure for interpretation to improve potency and overcome PZA resistance. We prepared and tested ring and carboxylic acid bioisosteres as well as 3, 5, 6 substitutions on the ring to study the structure activity relationships of the POA scaffold. All the analogs were evaluated for their whole cell antimycobacterial activity, and a few representative mols. were evaluated for their binding affinity, towards PanD, through isothermal titration calorimetry. We report that analogs with ring and carboxylic acid bioisosteres did not significantly enhance the antimicrobial activity, whereas the alkylamino-group substitutions at the 3 and 5 position of POA were found to be up to 5 to 10-fold more potent than POA. Further development and mechanistic anal. of these analogs may lead to a next generation POA analog for treating TB.

Keywords: Tuberculosis ; Pyrazinoic acid ; pyrazinamide

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Giri R. Gnawali ; Koichi Okumura ; Karolina Perez , et al. DOI: PubMed ID:

Abstract: Compound VBT-5445 was identified as an inhibitor to block the association of Pim and the protein Enhancer of Decapping 3 (EDC3), a Pim substrate, which normally functions to enhance the decapping of messenger RNA (mRNA). It was also shown to inhibit both the Pim and mTORC protein kinases. The activity of this compound class can be fine-tuned by structural modification. A series of VBT analogs were designed, synthesized, and evaluated. These compounds decrease the growth of multiple cancer types, including pancreas, prostate, breast, lung, and leukemia. Notably, 6-methyl (GRG-1-31, 6d), 4-chloro (GRG-1-34, 6e), 4-Bromo (GRG-1-35, 6f), and phenylthio substituted (GRG-1-104, 6n) derivatives are highly potent at inhibiting tumor growth. The ability of these compounds to block cancer growth in vitro is highly correlated with their activity as mTORC inhibitors. The toxicity of GRG 1–34 is low in mice treated with twice-daily gavage for 30 days and did not induce weight loss. Pharmacokinetics of a single oral dose demonstrated a peak concentration at 0.5?h after gavage. In summary, further development of this compound class has the potential to inhibit important signaling pathways and impact cancer treatment.

Keywords: Quinoline derivatives ; Pim kinase ; Antitumor activity ; mTORC

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Nazanin Mokhtarpour ;

Abstract: Reactive oxygen species (ROS) are a heterogeneous group of highly reactive ions and molecules derived from molecular oxygen (O 2), which can cause DNA damage and lead to skin cancer. High levels of ROS can promote cancer development, cancer cell survival, and resistance to chemotherapeutics. NADPH oxidase (NOX) is a significant producer of ROS in the cell. NOX1 generates two superoxide molecules by reducing NADPH. This only occurs when the membrane-bound NOX cytochrome p450 alpha chain (CYBA) binds to the organizer subunit NOXO1 from the cytosolic portions of the holoenzyme on the cell surface. We propose that stopping NOX1 complex subunits from coming together at this CYBA-NOXO1 junction is a potential way to prevent ROS production in human skin cells when exposed to ultraviolet rays. This dissertation investigates potential small-molecule inhibitors of the crucial NOX1 holoenzyme to solve these issues. We designed and synthesized NOX1 specific Inhibitor 1 using a diapocyin backbone structure. Computational docking studies were used to optimize inhibitor design and evaluate the NOXO1 protein subunit specificity. Due to increased binding interaction with NOXO1 protein and to improve solubility of solution preparation for further physical binding studies, we modified Inhibitor 1 and synthesized Inhibitor 2 by adding the NHS-ester Biotin polyethylene glycol chain to the piperidine ring. Both inhibitors were found to be non-toxic in human keratinocyte cells. The Inhibitor 2 reduced the cyclobutene pyrimidine dimer (CPD) DNA mutation in a human skin explant model. Finally, the isothermal calorimetric (ITC) binding assay and MALDI-TOF mass spectrometry were used for physical binding studies to evaluate the critical molecular interaction, leading to the decreased binding affinity of Inhibitor 1, Inhibitor 2, resulting in additional modifications seen in Inhibitor 3 and Inhibitor 4. The results demonstrate that Inhibitor 2 and Inhibitor 3 reduced the binding affinity between NOXO1 protein and CYBA membrane peptide because of a higher binding interaction of the inhibitors with NOXO1 protein, due to the interaction of the polyethylene glycol chain. In the second section of the project, we computationally design and synthesize NOX1-specific inhibitors using the sequence of CYBA peptides as a modeling tool. Through docking studies, we demonstrated inhibitor interference with NOX1 complexes. Several molecules were designed computationally, and three candidate compounds were tested in vitro and demonstrated a reduction of UVR damage in keratinocyte cells. Biophysical studies, like ITC, were performed to identify interactions. Through these studies, an understanding of protein-protein interactions was gained that are essential for discovering and validating inhibitor candidates, along with information for future inhibitor design. To determine the optimum strategy to utilize the biological features of the small molecule NM-166, a structure-activity relationship analysis was performed.

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Product Details of [ 103-67-3 ]

CAS No. :103-67-3 MDL No. :
Formula : C8H11N Boiling Point : -
Linear Structure Formula :C6H5CH2NH(CH3) InChI Key :RIWRFSMVIUAEBX-UHFFFAOYSA-N
M.W : 121.18 Pubchem ID :7669
Synonyms :
Chemical Name :N-Methyl-1-phenylmethanamine

Calculated chemistry of [ 103-67-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 39.02
TPSA : 12.03 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.96 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.94
Log Po/w (XLOGP3) : 1.52
Log Po/w (WLOGP) : 1.25
Log Po/w (MLOGP) : 1.87
Log Po/w (SILICOS-IT) : 1.86
Consensus Log Po/w : 1.69

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.91
Solubility : 1.49 mg/ml ; 0.0123 mol/l
Class : Very soluble
Log S (Ali) : -1.38
Solubility : 5.04 mg/ml ; 0.0416 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.19
Solubility : 0.0777 mg/ml ; 0.000641 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.0

Safety of [ 103-67-3 ]

Signal Word:Danger Class:8
Precautionary Statements:P210-P260-P280-P305+P351+P338-P310 UN#:2735
Hazard Statements:H227-H314-H317-H334 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 103-67-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 103-67-3 ]

[ 103-67-3 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 127-17-3 ]
  • [ 103-67-3 ]
  • [ 600-21-5 ]
  • 2
  • [ 1194-21-4 ]
  • [ 103-67-3 ]
  • [ 37409-94-2 ]
  • 3
  • [ 57-55-6 ]
  • [ 103-67-3 ]
  • [ 2568-25-4 ]
  • 5
  • [ 132898-96-5 ]
  • [ 103-67-3 ]
  • [ 869224-04-4 ]
YieldReaction ConditionsOperation in experiment
15% With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; chloroform; at 0 - 20℃; for 2.58333h; Step 1: N-Benzyl-N-methyl-2,3-dioxoindoline-5-sulfonamide To a black solution of 2,3-Dioxo-2,3-dihydro-1H-indole-5-sulfonylchloride (4.00 g, 16.3 mmol) in 1:1 THF:CHCl3 was added, drop-wise via syringe pump, a solution of N-benzylmethylamine (2.73 mL, 21.2 mmol, 1.3 eq) and N,N-diisopropylethylamine (5.68 mL, 32.6 mmol, 2 eq) in CHCl3 (32 mL) over a period of 1.25 hr. with cooling in an ice bath. After stirring for 50 min. the reaction was allowed to warm to room temperature and stirred for 30 minutes. The reaction was concentrated. The crude product was purified on Biotage KP silica gel eluding with 98/2 CHCl2/CH3OH to give the analytically pure sample of the title compound as a bright yellow solid (0.18 g, 15% yield). Anal. Calc'd for C16H14N2O4S: C, 58.17; H, 4.27; N, 8.48; Found: C, 57.88; H, 4.36; N, 8.40; MS: (API-ES-) m/z 329 [M-H]. m.p.: 183-185 C.
  • 6
  • [ 703-67-3 ]
  • [ 103-67-3 ]
  • 2-(N-benzylmethylamino)methyl-6-fluoro-3,4-dihydro-2H-naphthalene-1-one hydrochloride [ No CAS ]
  • [ 529-34-0 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; paraformaldehyde; In ethanol; water; Step D 2-(N-Benzylmethylamino)methyl-6-fluoro-3,4-dihydro-2H-naphthalene-1-one hydrochloride To an ice-cooled solution of N-benzylmethylamine (5.67 cm3) in ethyl alcohol (60 cm3) was added hydrochloric acid (5 M, 10 cm3). <strong>[703-67-3]6-Fluoro-3,4-dihydro-2H-naphthalene-1-one</strong> (6.00 g) and paraformaldehyde (1.32 g) were then added and the resulting mixture was stirred and heated to reflux for 4 h. Upon cooling, the alcohol was removed under reduced pressure and water (100 cm3) was added. The remaining tetralone was extracted into diethyl ether (100 cm3) and the aqueous mixture was then extracted further with dichloromethane (2*100 cm3). The combined extracts were dried (Na2SO4) and concentrated under reduced pressure. Trituration with diethyl ether and filtration provided the title compound (3.18 g) as a white solid.
  • 7
  • [ 149057-19-2 ]
  • [ 103-67-3 ]
  • [ 1311150-40-9 ]
  • 8
  • [ 1532-71-4 ]
  • [ 103-67-3 ]
  • [ 132997-51-4 ]
  • 10
  • [ 383-62-0 ]
  • [ 103-67-3 ]
  • N-benzyl-2-chloro-2,2-difluoro-N-methylacetamide [ No CAS ]
  • 11
  • [ 407-97-6 ]
  • [ 103-67-3 ]
  • N-benzyl-5-fluoro-N-methylpentan-1-amine [ No CAS ]
  • 12
  • [ 407-97-6 ]
  • [ 103-67-3 ]
  • C13H20N(1+) [ No CAS ]
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