Tag: M.W=300-350

Shahar, Or David published the artcileA high-throughput chemical screen with FDA approved drugs reveals that the antihypertensive drug Spironolactone impairs cancer cell survival by inhibiting homology directed repair, Name: 4-(3-(4-Butoxyphenoxy)propyl)morpholine hydrochloride, the publication is Nucleic Acids Research (2014), 42(9), 5689-5701, database is CAplus and MEDLINE.

DNA double-strand breaks (DSBs) are the most severe type of DNA damage. DSBs are repaired by non-homologous end-joining or homol. directed repair (HDR). Identifying novel small mols. that affect HDR is of great importance both for research use and therapy. Mols. that elevate HDR may improve gene targeting, whereas inhibiting mols. can be used for chemotherapy, since some of the cancers are more sensitive to repair impairment. Here, the authors performed a high-throughput chem. screen for FDA approved drugs, which affect HDR in cancer cells. The authors found that HDR frequencies are increased by retinoic acid and Idoxuridine and reduced by the antihypertensive drug Spironolactone. The authors further revealed that Spironolactone impairs Rad51 foci formation, sensitizes cancer cells to DNA damaging agents, to Poly (ADP-ribose) polymerase (PARP) inhibitors and crosslinking agents and inhibits tumor growth in xenografts, in mice. This study suggests Spironolactone as a new candidate for chemotherapy.

Nucleic Acids Research published new progress about 637-58-1. 637-58-1 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is 4-(3-(4-Butoxyphenoxy)propyl)morpholine hydrochloride, and the molecular formula is C18H12ClNO, Name: 4-(3-(4-Butoxyphenoxy)propyl)morpholine hydrochloride.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Aleyasin, Hossein published the artcileAntihelminthic Benzimidazoles Are Novel HIF Activators That Prevent Oxidative Neuronal Death via Binding to Tubulin, Safety of 4-(3-(4-Butoxyphenoxy)propyl)morpholine hydrochloride, the publication is Antioxidants & Redox Signaling (2015), 22(2), 121-134, database is CAplus and MEDLINE.

Aims: Pharmacol. activation of the adaptive response to hypoxia is a therapeutic strategy of growing interest for neurol. conditions, including stroke, Huntington’s disease, and Parkinson’s disease. We screened a drug library with known safety in humans using a hippocampal neuroblast line expressing a reporter of hypoxia-inducible factor (HIF)-dependent transcription. Results: Our screen identified more than 40 compounds with the ability to induce hypoxia response element-driven luciferase activity as well or better than deferoxamine, a canonical activator of hypoxic adaptation. Among the chem. entities identified, the antihelminthic benzimidazoles represented one pharmacophore that appeared multiple times in our screen. Secondary assays confirmed that antihelminthics stabilized the transcriptional activator HIF-1α and induced expression of a known HIF target gene, p21^cip1/waf1, in post-mitotic cortical neurons. The on-target effect of these agents in stimulating hypoxic signaling was binding to free tubulin. Moreover, antihelminthic benzimidazoles also abrogated oxidative stress-induced death in vitro, and this on-target effect also involves binding to free tubulin. Innovation and Conclusions: These studies demonstrate that tubulin-binding drugs can activate a component of the hypoxic adaptive response, specifically the stabilization of HIF-1α and its downstream targets. Tubulin-binding drugs, including antihelminthic benzimidazoles, also abrogate oxidative neuronal death in primary neurons. Given their safety in humans and known ability to penetrate into the central nervous system, antihelminthic benzimidazoles may be considered viable candidates for treating diseases associated with oxidative neuronal death, including stroke. Antioxid. Redox Signal. 22, 121-134.

Antioxidants & Redox Signaling published new progress about 637-58-1. 637-58-1 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is 4-(3-(4-Butoxyphenoxy)propyl)morpholine hydrochloride, and the molecular formula is C17H28ClNO3, Safety of 4-(3-(4-Butoxyphenoxy)propyl)morpholine hydrochloride.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Thoma, K. published the artcileColloid association and bioavailability of local anesthetics. Part 6. Mixed micelle formation with polysorbates, Product Details of C17H28ClNO3, the publication is Pharmaceutica Acta Helvetiae (1988), 63(4-5), 102-10, database is CAplus and MEDLINE.

For 19 surface-active local anesthetics, the binding to polyethylene glycol sorbitan fatty acid esters (I) by formation of mixed micelles was determined All surface-active local anesthetics investigated, except procaine-HCl and lidocaine-HCl, form mixed micelles with I. In the presence of 5% I in water, this binding fluctuates between 5.3% for butacaine sulfate and 75% for cyclomethycaine-sulfate. For all local anesthetics the quotient of the total concentration and the free moiety is proportional to the surfactant concentration The surfactant bound moiety of the local anesthetic is constant when it is below its critical micellar concentration (CMC). Above the CMC, deviations from this rule are observed The binding of tetracaine-HCl to I by mixed micelles formation demonstrates that the binding to these surfactants increases with the shortened fatty acid chain (that means an increasing HLB-value). When the pH-value or ionic strength increases, stadacain-HCl exhibits a distinct increase of the binding by a change of the dissociation-rate or a salting-out effect. Changing the solvent of stadacain-HCl from water to saline, for example, increases the binding to 5% I from 38.1 to 68%.

Pharmaceutica Acta Helvetiae published new progress about 637-58-1. 637-58-1 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is 4-(3-(4-Butoxyphenoxy)propyl)morpholine hydrochloride, and the molecular formula is C19H14N2, Product Details of C17H28ClNO3.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Thoma, K. published the artcileColloid association and bioavailability of local anesthetics. Part 7. Partition behavior, Safety of 4-(3-(4-Butoxyphenoxy)propyl)morpholine hydrochloride, the publication is Pharmaceutica Acta Helvetiae (1988), 63(6), 155-9, database is CAplus and MEDLINE.

The partition coefficient was determined for 20 local anesthetics and was found to be considerably influenced by the chem. structure and the substituents present in the compounds In the system n-octanol/buffer (pH 5.7) partition coefficients between 0.05 (brufacaine-HCl) and 199.0 (chinisocaine-HCl) were found. In the system n-octanol/water they ranged between 0.003 (procaine-HCl and lidocaine-HCl) and 4.2 (oxetacaine-HCl). Raising the pH-value from 4 to 6 resulted in an increase of the partition coefficient of stadacain-HCl from 8.9 to 56.5. Raising the ionic strength from 0.2 to 1.0 of a pH 5.7 buffer increased the partition coefficient of stadacain-HCl from 30.4 to 95.3%. The addition of 5.0% NaCl to an aqueous, unbuffered solution of stadacain-HCl increased the partition coefficient from 0.36 to 27.2.

Pharmaceutica Acta Helvetiae published new progress about 637-58-1. 637-58-1 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is 4-(3-(4-Butoxyphenoxy)propyl)morpholine hydrochloride, and the molecular formula is C5H5BrN2, Safety of 4-(3-(4-Butoxyphenoxy)propyl)morpholine hydrochloride.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Hattori, Hiromu published the artcileTotal Synthesis of Tiacumicin A. Total Synthesis, Relay Synthesis, and Degradation Studies of Fidaxomicin (Tiacumicin B, Lipiarmycin A3), Related Products of ethers-buliding-blocks, the publication is Journal of Organic Chemistry (2018), 83(13), 7180-7205, database is CAplus and MEDLINE.

The com. macrolide antibiotic fidaxomicin was synthesized in a highly convergent manner. Salient features of this synthesis include a β-selective noviosylation, a β-selective rhamnosylation, a ring closing metathesis, a Suzuki coupling and a vinylogous Mukaiyama aldol reaction. Careful choice of protecting groups and fine tuning of the glycosylation reactions led to the first total synthesis of fidaxomicin. In addition, a relay synthesis of fidaxomicin was established, which gives access to a conveniently protected intermediate from the natural material for derivatization. The first total synthesis of a related congener, tiacumicin A, is presented.

Journal of Organic Chemistry published new progress about 99438-28-5. 99438-28-5 belongs to ethers-buliding-blocks, auxiliary class Chiral,Aliphatic cyclic hydrocarbon, name is (+)-B-Methoxydiisopinocampheylborane, and the molecular formula is C21H37BO, Related Products of ethers-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Nicolaou, K. C. published the artcileTotal Synthesis and Biological Evaluation of Monorhizopodin and 16-epi-Monorhizopodin, Safety of (+)-B-Methoxydiisopinocampheylborane, the publication is Angewandte Chemie, International Edition (2011), 50(5), 1139-1144, S1139/1-S1139/94, database is CAplus and MEDLINE.

A highly convergent total synthesis of monorhizopodin (I) and 16-epi-monorhizopodin was developed, rendering the monomeric homologs of the powerful antitumor agent rhizopodin available for biol. investigations. Preliminary studies showed these compounds to be endowed with actin-binding properties but devoid of any associated cytotoxicity, thus posing interesting questions regarding the role of the dimeric nature of rhizopodin in its mode of action. Further studies directed toward the elucidation of the mechanism of action and the differences of rhizopodin and its monomeric homologs, monorhizopodin and 16-epi-monorhizopodin, as well as the total synthesis of the former are in progress.

Angewandte Chemie, International Edition published new progress about 99438-28-5. 99438-28-5 belongs to ethers-buliding-blocks, auxiliary class Chiral,Aliphatic cyclic hydrocarbon, name is (+)-B-Methoxydiisopinocampheylborane, and the molecular formula is C21H37BO, Safety of (+)-B-Methoxydiisopinocampheylborane.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Hu, Shaojing published the artcileDiastereoselective chloroallylboration of α-chiral aldehydes, Category: ethers-buliding-blocks, the publication is Journal of Organic Chemistry (1998), 63(24), 8843-8849, database is CAplus.

Double asym. reaction of chiral (Z)-(γ-chloroallyl)diisopinocampheylboranes, d-I and l-I, with α-chiral aldehydes (S)-MeCH₂CHMeCHO, N-Boc-L-valinal (II), (R)-2,3-O-isopropylidnene-D-glyceraldehyde, and (R)- and (S)-Me₃CSiMe₂OCH₂CHMeCHO provide a new practical method for the generation of 2,3-syn-3,4-anti and 2,3-syn-3,4-syn chiral vinylchlorohydrins and vinyl epoxides. Both enantiomers d-I and l-I exhibited excellent diastereoselectivity (≥90 de) for matched cases. The mismatched cases yielded moderate to good diastereoselectivity. Thus, l-I was generated in situ from allyl chloride and l-B-methoxydiisopinocampheylborane by treatment with Li dicyclohexylamide and F₃B.OEt₂ in Et₂O/THF and reacted with II at -95° for four hours to give 60% of 99:1 mixture of vinyl chlorohydrins III and IV. Similar reaction of II with d-I gave 61% of a 15:85 mixture of III and IV. Cyclization of III in MeOH containing K₂CO₃ gave 98% vinyloxirane V.

Journal of Organic Chemistry published new progress about 99438-28-5. 99438-28-5 belongs to ethers-buliding-blocks, auxiliary class Chiral,Aliphatic cyclic hydrocarbon, name is (+)-B-Methoxydiisopinocampheylborane, and the molecular formula is C21H37BO, Category: ethers-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Hu, Shaojing published the artcileDiastereo- and Enantioselective Synthesis of syn-α-Vinylchlorohydrins and cis-Vinylepoxides, Formula: C21H37BO, the publication is Journal of Organic Chemistry (1996), 61(21), 7513-7520, database is CAplus and MEDLINE.

A new method to generate chiral syn-vinylchlorohydrins and cis-vinyloxiranes is reported. Reaction of (α-haloallyl)lithiums with methoxy-9-BBN or Ipc₂BOMe followed by treatment with BF₃·OEt₂ leads to (Z)-(γ-haloallyl)boranes which react with aldehydes to yield cis-vinylepoxides (de ≥ 90%) upon oxidative workup. Alternatively, addition of ethanolamine to the allylboration product yields syn-α-halohydrins (de ≥ 90%) that are also easily cyclized to cis-vinylepoxides. Extension of this protocol using [(Z)-γ-chloroallyl]BIpc₂ leads to chiral syn-α-chlorohydrins and cis-vinylepoxides in high de (≥90%) and ee (90-99%). Enantioselectivity of reactions of chiral (Z)-(γ-chloroallyl)boranes with aldehydes are more sensitive to reaction conditions than enantioselectivity of reactions of other α- or γ-substituted allylboranes. The effects of proportion of BF₃·OEt₂ and the relative efficacies of LiNR₂ bases on diastereo- and enantioselectivity of the chloroallylation are reported.

Journal of Organic Chemistry published new progress about 99438-28-5. 99438-28-5 belongs to ethers-buliding-blocks, auxiliary class Chiral,Aliphatic cyclic hydrocarbon, name is (+)-B-Methoxydiisopinocampheylborane, and the molecular formula is C21H37BO, Formula: C21H37BO.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

De Joarder, Dripta published the artcileEnantioselective synthesis of a potential 1,5-syn-polyol C1-C24 subunit of (-)-caylobolide A, Safety of (+)-B-Methoxydiisopinocampheylborane, the publication is Tetrahedron Letters (2013), 54(43), 5826-5829, database is CAplus.

The synthesis of a protected possible 1,5-syn-polyol C(1)-C(24) subunit, I (TES = Et₃Si), resident in (-)-caylobolide A was accomplished. The key reaction sequence was a repetitive protocol for the construction of the syn-1,5-diol segment by Ru-catalyzed cross-metathesis and B-mediated allylation reactions.

Tetrahedron Letters published new progress about 99438-28-5. 99438-28-5 belongs to ethers-buliding-blocks, auxiliary class Chiral,Aliphatic cyclic hydrocarbon, name is (+)-B-Methoxydiisopinocampheylborane, and the molecular formula is C21H37BO, Safety of (+)-B-Methoxydiisopinocampheylborane.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Brown, Herbert C. published the artcileChiral synthesis via organoboranes. 13. A highly diastereoselective and enantioselective addition of [(Z)-γ-alkoxyallyl]diisopinocampheylboranes to aldehydes, COA of Formula: C21H37BO, the publication is Journal of the American Chemical Society (1988), 110(5), 1535-8, database is CAplus.

Isomerically pure [(Z)-γ-methoxyallyl]diisopinocampheylboranes, I, prepared from (+)-α-pinene and II, have been prepared from B-methoxydiisopinocampheylborane and lithiated allyl Me ether. These enantiomeric [(Z)-γ-methoxyallyl]diisopinocampheylboranes retain their stereochem. identity under the reaction conditions. They have been successfully condensed with various aldehydes, such as acetaldehyde, propionaldehyde, 2-methylpropionaldehyde, and benzaldehyde in a regioselective and stereoselective manner to yield the corresponding threo-β-methoxyhomoallyl alcs. in â‰?9% diastereoselectivities and â‰?5% enantioselectivities. Similarly, [(Z)-γ-[(methoxymethyl)oxy]allyl]diisopinocampheylborane was prepared and was utilized for the preparation of threo-1,2-diol.

Journal of the American Chemical Society published new progress about 99438-28-5. 99438-28-5 belongs to ethers-buliding-blocks, auxiliary class Chiral,Aliphatic cyclic hydrocarbon, name is (+)-B-Methoxydiisopinocampheylborane, and the molecular formula is C21H37BO, COA of Formula: C21H37BO.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem