(-)-borneol | 507-70-0

• 物质功能分类: 原料药 - 人工合成抗感染类药 - 消毒防腐药
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (-)-borneol
• 英文别名: (1S-endo)-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-ol；DL-Borneol；(1S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol
• CAS: 507-70-0
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: DTGKSKDOIYIVQL-SFVIPPHHSA-N

物化性质

• 熔点：
  206-209 °C
• 比旋光度：
  -0.5～+0.5゜(20℃/D)(c=5,C2H5OH)
• 沸点：
  210 °C(lit.)
• 密度：
  1.011
• 蒸气密度：
  5.31 (vs air)
• 闪点：
  150 °F
• 溶解度：
  DMSO:30.0(最大浓度 mg/mL);194.49(最大浓度 mM)乙醇:30.0(最大浓度 mg/mL);194.49(最大浓度 mM)
• LogP：
  3.6 at 20℃
• 物理描述：
  Borneol appears as a white colored lump-solid with a sharp camphor-like odor. Burns readily. Slightly denser than water and insoluble in water. Used to make perfumes.
• 颜色/状态：
  White to off-white crystals
• 气味：
  Piney, camphor-like odor
• 味道：
  Burning taste somewhat reminiscent of mint
• 蒸汽压力：
  5.02X10-2 mm Hg at 25 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

ADMET

毒理性

• 相互作用

为了研究冰片对具有不同亲水性和分子大小的化合物经角膜透过性的增强效果。选择了六种化合物作为模型药物，分别是罗丹明B、荧光素钠、异硫氰酸荧光素（FITC）葡聚糖4、10、20和40 kDa。透过性研究使用兔眼角膜离体样本，通过Franz型扩散装置进行。评估冰片的安全性基于角膜水合水平和Draize眼刺激性试验。将0.2%冰片应用于角膜，使罗丹明B、荧光素钠、4和10 kDa FITC-葡聚糖的表观透过系数分别增加了1.82倍（p<0.05）、2.49倍（p<0.05）、4.18倍（p<0.05）和不显著地1.11倍。与对照组相比，10、20和40 kDa FITC-葡聚糖与冰片没有显著透过性增强。0.2%冰片增强的透过系数与模型药物的分子量呈线性相关（R(2)=0.9976）。应用0.05%、0.1%和0.2%冰片后，角膜水合值小于83%，Draize评分小于4。冰片可能改善亲水性和疏水性化合物的经角膜渗透，而不引起毒性反应，尤其是亲水性化合物。此外，0.2%冰片可以增强分子量小于或等于4 kDa的亲水性化合物的透过性。因此，冰片可以被认为是一种安全有效的眼用药物渗透增强剂。

To investigate the enhancing effect of borneol on transcorneal permeation of compounds with different hydrophilicities and molecular sizes. Six compounds, namely rhodamine B, sodium-fluorescein, fluorescein isothiocyanate (FITC) dextrans of 4, 10, 20 and 40 kDa were selected as model drugs. Permeation studies were performed using excised cornea of rabbits by a Franz-type diffusion apparatus. The safety of borneol was assessed on the basis of corneal hydration level and Draize eye test. The application of 0.2% borneol to the cornea increased the apparent permeability coefficient by 1.82-(p<0.05), 2.49-(p<0.05), 4.18-(p<0.05), and 1.11-fold (not significant) for rhodamine B, sodium-fluorescein, FITC-dextrans of 4 and 10 kDa, respectively. No significant permeability enhancement of FITC dextrans of 10, 20 and 40 kDa with borneol was found compared to control. The permeability coefficient enhanced by 0.2% borneol was linear correlated to the molecular weight of model drugs (R(2)=0.9976). With the 0.05%, 0.1% and 0.2% borneol application, the corneal hydration values were <83% and Draize scores were <4. Borneol may improve the transcorneal penetration of both hydrophilic and lipophilic compounds without causing toxic reactions, especially hydrophilic ones. Furthermore, 0.2% borneol can enhance the permeation of hydrophilic compounds with molecular weight </= 4 kDa. Hence, borneol can be considered as a safe and effective penetration enhancer for ocular drug administration.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

这项研究旨在通过MTT实验、流式细胞术和Western印迹法调查自然冰片/姜黄素（NB/Cur）对A375人类黑色素瘤细胞系生长和凋亡的协同效应。我们的结果显示，NB有效地与Cur协同作用，增强了对A375人类黑色素瘤细胞的抗增殖活性，通过诱导凋亡，表现为亚G1细胞群体增加、DNA断裂、PARP裂解和caspase活化。进一步的机制研究通过Western印迹法显示，细胞经NB/Cur处理后，磷酸化JNK表达水平上调和磷酸化ERK和Akt表达水平下调，促使A375细胞凋亡。此外，NB还增强了Cur触发细胞内ROS过度产生和DNA损伤的能力，同时上调了磷酸化ATM、磷酸化Brca1和磷酸化p53的表达水平。结果表明，NB和Cur联合应用在癌症治疗中具有潜在的应用价值。

This study was to investigate the synergistic effect of natural borneol/curcumin (NB/Cur) on growth and apoptosis in A375 human melanoma cell line by MTT assay, flow cytometry and Western blotting. Our results demonstrated that NB effectively synergized with Cur to enhance its antiproliferative activity on A375 human melanoma cells by induction of apoptosis, as evidenced by an increase in sub-G1 cell population, DNA fragmentation, PARP cleavage, and caspase activation. Further mechanistic studies by Western blotting showed that after treatment of the cells with NB/Cur, up-regulation of the expression level of phosphorylated JNK and down-regulation of the expression level of phosphorylated ERK and Akt contributed to A375 cells apoptosis. Moreover, NB also potentiated Cur to trigger intracellular ROS overproduction and the DNA damage with up-regulation of the expression level of phosphorylated ATM, phosphorylated Brca1 and phosphorylated p53. The results indicate the combinational application potential of NB and Cur in treatments of cancers.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

识别和使用：冰片是一种固体。它被用作香料，并作为药物使用，包括传统中医。人类暴露和毒性：冰片不会引起皮肤过敏。其毒性实质上与樟脑相似。人类外周血淋巴细胞在DMSO中暴露于不同浓度的l-冰片，浓度高达600微克/毫升，持续4小时，有和无代谢激活以及24小时无代谢激活。在研究的条件下，l-冰片被认为不具有致裂变性。动物研究：与樟脑类似，实验室动物对冰片的毒性似乎比人类要小得多。冰片增加了大鼠口服处理7天后CYP2D的活性。冰片在小鼠中已被评估其镇痛和抗炎活性。冰片在爪子舔舐的早期和晚期显著减少了痛觉行为，并减少了小鼠的扭动反射。当进行热板测试时，高剂量的冰片产生了痛觉行为的抑制。此外，冰片处理的小鼠减少了角叉菜胶诱导的白细胞迁移到腹腔。冰片的致突变潜力在Ames试验中以Salmonella typhimurium TA1535、TA1537、TA1538、TA98和TA100菌株为对象进行了评估，冰片浓度高达5000微克/平板，在存在和不存在代谢激活的情况下。其他研究也证实了在S. typhimurium TA98和TA100菌株中缺乏致突变潜力。在研究的条件下，冰片被认为在细菌中不具有致突变性。

IDENTIFICATION AND USE: Borneol is a solid. It is used as a flavoring, and as a medication, including traditional Chinese medicine. HUMAN EXPOSURE AND TOXICITY: Borneol does not present a concern for skin sensitization. Toxicity is essentially indistinguishable from that of camphor. Human peripheral blood lymphocytes were exposed to varying concentrations of l-borneol in DMSO up to 600 ug/mL for 4 hr, with and without metabolic activation and 24 hr without metabolic activation. Under the conditions of the study, l-borneol was considered non-clastogenic. ANIMAL STUDIES: As with camphor, laboratory animals appear to be much less susceptible to borneol toxicity than man. Borneol increased the activity of CYP2D in rats orally treated by borneol for 7 days. Borneol has been evaluated for antinociceptive and anti-inflammatory activities in mice. Borneol produced a significant reduction of the nociceptive behavior at the early and late phases of paw licking and reduced the writhing reflex in mice. When the hot plate test was conducted, borneol (in higher dose) produced an inhibition of the nociceptive behavior. Additionally, borneol-treated mice had reduced the carrageenan-induced leukocytes migration to the peritoneal cavity. The mutagenic potential of borneol was assessed in an Ames test with Salmonella typhimurium strains TA1535, TA1537, TA1538, TA98 and TA100 treated with borneol at concentrations up to 5000 ug/ plate in the presence and absence of metabolic activation. Other studies confirming a lack of mutagenic potential in S. typhimurium strains TA98 and TA100 have been published. Under the conditions of the study, borneol is considered not mutagenic in bacteria.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

立即急救：确保已经进行了充分去污。如果患者停止呼吸，开始人工呼吸，最好使用需求阀复苏器、气囊面罩装置或口袋面罩，按训练进行操作。根据需要执行心肺复苏。立即用缓慢流动的水冲洗受污染的眼睛。不要催吐。如果发生呕吐，让患者前倾或置于左侧（如果可能的话，头部向下）以保持呼吸道畅通，防止吸入。保持患者安静，维持正常体温。寻求医疗帮助。/樟脑及其相关化合物/

Immediate First Aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Camphor and related compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

基本治疗：建立专利气道（如需要，使用口咽或鼻咽气道）。如有必要，进行吸痰。观察呼吸不足的迹象，如有必要，协助通气。通过非循环呼吸面罩以10至15升/分钟的速度给予氧气。预期可能出现癫痫，并尽量减少所有外部刺激。根据需要治疗癫痫……监测休克并视需要进行治疗……。对于眼睛污染，立即用水冲洗眼睛。在运输过程中，用0.9%的生理盐水（NS）连续冲洗每只眼睛……。不要使用催吐剂。对于摄入，如果患者能够吞咽，有强烈的呕吐反射，并且不流口水，则用水冲洗口腔，并给予5毫升/千克，最多200毫升的水进行稀释。给予活性炭……。/樟脑及其相关化合物/

Basic Treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Anticipate seizures and minimize all external stimuli. Treat seizures as necessary ... . Monitor for shock and treat as necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Camphor and related compounds/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

为了开发一种气相色谱-火焰离子化检测法（GC-FID）来测定冰片在小鼠组织中的浓度，并研究静脉注射和鼻腔给药后冰片的组织分布，收集了给予30.0 mg/kg冰片剂量后1、3、5、10、20、30、60、90、120分钟的小鼠大脑、心脏、肝脏、脾脏、肺和肾脏。用乙酸乙酯提取组织中的药物，并通过气相色谱检测冰片浓度，以十八烷为内标。校准曲线显示出良好的线性关系。提取回收率、日间和日内精密度以及稳定性符合生物样本分析的要求。冰片主要分布在大多数组织中，心脏、大脑和肾脏中较多，肝脏、脾脏和肺中较少。建立的GC-FID方法适用于组织中冰片含量的测定。在小鼠静脉注射和鼻腔给药后，冰片主要分布在血液供应丰富的组织中。在鼻腔给药后，大脑组织显示出最高的靶向系数和靶向效果。

To develop a GC-FID method to determine borneol's concentration in mouse tissues, and to investigate the tissue distribution after intravenous and intranasal administrations of borneol, mouse brains, hearts, livers, spleens, lungs and kidneys were collected at 1, 3, 5, 10, 20, 30, 60, 90, 120 min after administration of borneol with the dose of 30.0 mg/kg. The drug in tissues was extracted with ethyl acetate, and borneol's concentration detected by GC, with octadecane as the internal standard. The calibration curve showed a good linear relationship. Extraction recoveries, inter-day and intra-day precisions and stability were in conformity with the analytical requirements of biological samples. Borneol was mainly distributed in most tissues, more in heart, brain and kidney, and less in liver, spleen and lung. The established GC-FID method is applicable for content determination of borneol in tissues. After intravenous and intranasal administrations in mice, borneol is mainly distributed in abundant blood-supply tissues. After intranasal administration, brain tissues showed the highest target coefficient and target effectiveness.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

为了理解静脉注射、鼻腔给药或口服给药后血液和大脑的药物动力学，并探讨鼻腔给药的优越性和可行性，开发了一种带有火焰离子化检测（FID）的简单气相色谱（GC）方法，用于定量测定冰片。在给小鼠静脉注射、鼻腔给药或口服给药30.0 mg/kg冰片后，分别于1、3、5、10、20、30、60、90和120分钟收集血液样本和大脑。样品前处理是通过使用辛烷内标溶液的液-液萃取来进行的。药代动力学参数是通过计算机软件计算得出的。血浆和大脑中冰片的校准曲线分别在0.11-84.24 ug/mL和0.16-63.18 ug/g范围内呈线性。方法回收率和提取回收率均在85%-115%范围内。血浆和大脑样本的日内和日间变异性均小于或等于5.00%相对标准偏差（RSD）。鼻腔给药和口服给药的绝对生物利用度F分别为90.68%和42.99%。鼻腔给药和口服给药的相对脑靶向系数Re分别为68.37%和38.40%。所开发的GC-FID方法可用于测定和药代动力学研究。注射给药的冰片分布和代谢速度快，无需吸收过程。口服给药的冰片分布较慢，且绝对生物利用度最低。鼻腔给药的冰片能迅速吸收进入血液和大脑，使用方便，安全性大于感染，这使得它作为治疗脑病的给药途径值得进一步开发。

... In order to understand the blood and brain pharmacokinetics after intravenous, intranasal, or oral administration and to investigate the superiority and feasibility of intranasal administration, a simple gas chromatographic (GC) method with flame ionization detection (FID) was developed for the quantification of borneol. Blood samples and brain were collected from mice at 1, 3, 5, 10, 20, 30, 60, 90, and 120 min after intravenous, intranasal, or oral administration of borneol at a dosage of 30.0 mg/kg. Sample preparations were carried out by liquid-liquid extraction with an internal standard solution of octadecane. The pharmacokinetic parameters were calculated /using computer software/. The calibration curves were linear in the range of 0.11-84.24 ug/mL and 0.16-63.18 ug/g for borneol in plasma and brain, respectively. The methodological and extraction recoveries were both in the range of 85%-115%. The intra-day and inter-day variabilities for plasma and brain samples were </= 5.00% relative standard deviation (RSD). The absolute bioavailabilities F of intranasal and oral administrations were 90.68% and 42.99%. The relative brain targeted coefficients Re of intranasal and oral administrations were 68.37% and 38.40%. The GC-FID method developed could be applied to determination and pharmacokinetic study. The borneol from injection was distributed and metabolized fast without absorption process. The borneol from oral administration was distributed more slowly and had the lowest absolute bioavailability. Nasal administration of borneol was quickly absorbed into the blood and brain, was easy to use and had a greater safety than infection, which makes it worthy of further development as an administration route for encephalopathy treatment.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

这项工作的目的是研究冰片的原位和活体鼻腔吸收。应用了一种新颖的单次通过原位鼻腔灌注技术来检查大鼠鼻腔吸收冰片的速率和程度。研究了灌注速率、pH值和药物浓度等实验条件。原位实验显示，冰片的鼻腔吸收不依赖于药物浓度，并且符合一级过程。吸收速率常数Ka随着灌注速度的增加而变化。在鼻咽腔的生理条件下，冰片在pH范围内和pH值条件下被很好地吸收。在大鼠中进行了冰片吸收的活体研究，并比较了鼻腔内给药（in）与静脉给药（iv）的药代动力学参数。冰片鼻腔内给药的生物利用度为90.82%，达到最大浓度的时间Tmax为10分钟。平均滞留时间MRT分别为262.55 +/- 67.35分钟和204.22 +/- 14.50分钟，分别对应于鼻腔内给药和静脉给药。结果表明，冰片可以通过大鼠鼻腔内给药被迅速且彻底吸收。

The aim of this work was to study the in situ and in vivo nasal absorption of borneol. A novel single pass in situ nasal perfusion technique was applied to examine the rate and extent of nasal absorption of borneol by rats. Experimental conditions, such as perfusion rate, pH and drug concentration, were investigated. The in situ experiments showed that the nasal absorption of borneol was not dependent on drug concentration, and fitted a first order process. The absorption rate constant, Ka, influenced with an increase in perfusion speed. The borneol was well absorbed in the conditions of the nasal cavity within the pH range and pH value of physiological conditions. In vivo studies of borneol absorption were carried out in rats and the pharmacokinetics parameters of intranasal (in) was compared with intravenous (iv) administration. The bioavailabilities of borneol was 90.82% for i.n. while Tmax values were 10 min. MRT (Mean Residence Time) were 262.55 +/- 67.35 min and 204.22 +/- 14.50 min for in and iv methods, respectively. The results demonstrate that borneol could be absorbed promptly and thoroughly by in administration in rats.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

先前的研究表明，冰片对中枢神经系统（CNS）具有双重作用，但机制尚不清楚。本研究的目的是澄清兴奋比例[兴奋性氨基酸（AAs）含量与抑制性氨基酸含量之比]与单次口服给药后天然冰片含量的关系。小鼠通过口服摄入给予1.2 g/kg剂量的天然冰片（含98% D: -冰片）。在大鼠口服给药前和给药后0.083、0.167、0.25、0.333、0.5、0.75、1、1.5、2、2.5、3、4和5小时收集脑样本。通过GC-MS和HPLC-FLU分别测定小鼠脑中天然冰片的浓度和氨基酸神经递质的含量。口服给药后，天然冰片迅速吸收进入大脑，并在给药后5分钟内可检测到。给药后1小时达到最大脑浓度（86.52微克/克）。天然冰片能够影响小鼠脑中氨基酸神经递质的含量：L: -门冬氨酸从给药后0.083小时至1小时显著增加，L: -谷氨酸在0.333小时显著增加，并在1.5至5小时降低，γ-氨基丁酸从给药后0.167小时至5小时显著增加，而甘氨酸不受影响。兴奋比例是兴奋性氨基酸含量与抑制性氨基酸含量之比，反映了机体的兴奋或抑制状态。兴奋比例在给药后0.5小时暂时升高然后下降；在给药后1.5-5小时与给药前有显著差异。本研究表明，天然冰片能够影响氨基酸神经递质的含量，兴奋比例的变化导致冰片对CNS的双重作用。

Previous studies have indicated that borneol has double side effects on the central nervous system (CNS), but the mechanism is unknown. The aim of this study was to clarify the relationship between excitation ratio [contents of excitatory amino acids (AAs) versus that of inhibitory] and the content of natural borneol after a single oral dose. Mice were administered a 1.2 g/kg dose of natural borneol (containing 98% D: -borneol) by oral ingestion. Brain samples were collected before administration and at 0.083, 0.167, 0.25, 0.333, 0.5, 0.75, 1, 1.5, 2, 2.5, 3, 4, and 5 hr after administration. The brain concentration of natural borneol and contents of AA neurotransmitters in mice brain were determined by GC-MS and HPLC-FLU, respectively. After per oral application, natural borneol was absorbed rapidly into the brain and could be determined 5 min after dosing. The maximal brain concentration (86.52 ug/g) was reached after 1 hr post-dosing. Natural borneol could affect the contents of AA neurotransmitters in mice brain: L: -aspartic acid increased significantly from 0.083 to 1 hr after administration, L: -glutamic acid increased significantly at 0.333 hr and decreased from 1.5 to 5 hr, gamma-amino-N-butyric acid increased significantly from 0.167 to 5 hr, whereas glycine was not affected. The excitation ratio is the contents of excitatory AAs versus that of inhibitory AAs, which reflects the excitatory or inhibitory state of the body. The excitation ratio elevated transitorily and then declined 0.5 hr post-dosing; there were significant differences between 1.5-5 hr post-dose compared with pre-dose. The present study indicated that natural borneol could affect the contents of AA neurotransmitters, and the change in excitatory ratio led to borneol's double side effects on the CNS.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险等级：
  4.1
• 危险品标志：
  F
• 安全说明：
  S16,S36/37
• 危险类别码：
  R22,R11
• WGK Germany：
  2
• 海关编码：
  2906199090
• 危险品运输编号：
  UN 1312
• 危险类别：
  4.1
• RTECS号：
  DT5095000
• 包装等级：
  III

制备方法与用途

性状：冰片为无色或白色透明的片状松脆结晶，或为结晶性粉末及块。在乙醇、氯仿、汽油中易溶，在水中几乎不溶。它呈强烈松树香、樟脑气息和薄荷气味。受热可升华，室温下可缓慢挥发，有灼热感。熔点为208℃，沸点212℃，闪点65.6℃，相对密度1.011（20℃）。不溶于水，溶于乙醇、乙醚和氯仿。

天然左旋体存在于肉豆蔻、小豆蔻、生姜等中，右旋体存在于芫荽子、香茅等中，消旋体存在于樟脑、迷迭香、百里香等中。

性质：冰片呈强烈松树香、樟脑气息和薄荷气味。受热可升华，室温下可缓慢挥发，有灼热感。熔点208℃（消旋体），沸点212℃，闪点65.6℃，相对密度1.011（20℃）。不溶于水，溶于乙醇、乙醚和氯仿。

用途：冰片广泛用于配制迷迭香、熏衣草等型香精，并用于制药。GB 2760-1996规定其为允许使用的食用香料，主要用于配制薄荷、白柠檬和果仁等型香精。此外，它还用作生化试剂，也用于医药工业。

生产方法：由樟脑溶于乙醇中用金属钠或新生态氢还原制取，也可由蒎烯经盐酸、镁粉等处理而成。

鉴别试验：

• 将试样与等量的百里酚混合研磨时，即变成液体。
• 取0.5g试样加2～3滴乙醚溶解后，加入4ml 20%重铬酸钾溶液和0.3ml浓硫酸，在温水中摇振加热，液体应呈红褐色，特异的香气消失而产生樟脑气味。

毒性：LD₅₀ 2000 mg/kg（兔子，经口）。GRAS（FEMA）。

使用限量：

• FEMA(mg/kg)：软饮料0.25～1.4；冷饮1.4；糖果3.7；焙烤食品5.1；胶姆糖0.30。

反应信息

• 作为反应物：
  描述：

  (-)-borneol 在 氯苯 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以100%的产率得到(1S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
  参考文献：
  名称：

  Selective oxidation of alcohols to aldehydes or ketones

  摘要：

  醇类经过氯代芳烃氧化剂和金属配体复合物或金属/配体组合氧化，生成它们对应的酮或醛。这种反应特别适用于芳香族醇和环状以及双环脂肪醇。

  公开号：

  US06350916B1

文献信息

• Discovery of a quinoline-based phenyl sulfone derivative as an antitrypanosomal agent
  作者：Huaisheng Zhang、Jasmine Collins、Rogers Nyamwihura、Shelbi Ware、Marcel Kaiser、Ifedayo Victor Ogungbe

  DOI：10.1016/j.bmcl.2018.03.039

  日期：2018.5

  A series of natural products-based phenyl sulfone derivative and their property-based analogues were investigated as potential growth inhibitors of Trypanosoma brucei. Trypanosoma brucei is a kinetoplastid protozoan parasite that causes trypanosomiasis. In this work, we found that nopol- and quinoline-based phenyl sulfone derivative were the most active and selective for T. brucei, and they were not

  研究了一系列基于天然产物的苯砜衍生物及其基于性质的类似物，作为布鲁氏锥虫的潜在生长抑制剂。布氏锥虫（Trypanosoma brucei）是一种运动型原生动物寄生虫，可引起锥虫病。在这项工作中，我们发现，nopol-和喹啉基苯基砜衍生物是最具有活性和选择性的锥虫，他们是不是对的活性巯基反应布氏锥虫的半胱氨酸蛋白酶罗得沙星。随后研究了喹啉基苯砜的硫醇反应性变体，发现它是罗得沙因的中度抑制剂。对罗得沙坦不发生反应的基于喹啉的化合物可以用作基于表型的先导发现的模板，而其硫醇活性的同源物可以作为基于模板的新抗锥虫药研究的模板。
• Environment friendly reagents and process for halogenoalkylsulfinylation of organic compounds
  申请人：VIRBAC S.A.

  公开号：EP1331222A1

  公开（公告）日：2003-07-30

  The invention concerns compounds corresponding to formula (I) : wherein: Y represents a group chosen from : a C1-C20, linear, branched or cyclic alkane di-yl, or alkene di-yl, or alkyne di-yl radical, wherein said alkane, alkene or alkyne chain can be substituted by one or more groups chosen from : a phenyl ring or a halogen atom, and said alkane, alkene or alkyne chain can comprise a sulfur bridge or an oxygen bridge ; R represents an alkyl group, linear or branched, comprising one to four carbon atoms and substituted by one or more, identical or different, halogen atoms ; a process for their preparation and their use as halogenoalkylsulfinylating agents.

  该发明涉及与以下公式（I）对应的化合物：其中：Y代表从中选择的一组基团：C1-C20的直链、支链或环烷烃二基、烯烃二基或炔烃二基，其中所述的烷烃、烯烃或炔烃链可以被一个或多个从以下选择的基团取代：苯环或卤素原子，并且所述的烷烃、烯烃或炔烃链可以包含硫桥或氧桥；R代表一个含有一到四个碳原子的直链或支链烷基，并且被一个或多个相同或不同的卤素原子取代；一种用于它们的制备和作为卤代烷基磺酰化剂的使用方法。
• 2-Oxabicyclo[3.3.0]octane compounds, process for producing the same, optical resolver, method of separating diastereomer mixture, and method of optically resolving alcohol
  申请人：Sakamoto Kei

  公开号：US20060205960A1

  公开（公告）日：2006-09-14

  2-Oxabicyclo[3.3.0]octane compounds represented by the following formula (1) (compound (1)); an optical resolver comprising at least one of the compounds (1); a process for producing the compounds (1) which comprises reacting a compound (2) or compound (3) with an alcohol (5) in the presence of an acid catalyst; a method of separating a diastereomer mixture of a compound (1); and a method of optically resolving an alcohol with the optical resolver. In the formulae, R 1 to R 10 each represents hydrogen atom, etc.; R 11 represents an alkyl group, etc.; R 12 represents a hydrocarbon group, etc.; R 13 represents a hydrocarbon group, etc.; and A represents acetyl group, etc.]

  以下是2-Oxabicyclo[3.3.0]辛烷化合物的化学式（1）（化合物（1））；包含至少一种化合物（1）的光学分离剂；制备化合物（1）的过程，包括在酸催化剂存在下将化合物（2）或化合物（3）与醇（5）反应；分离化合物（1）的对映异构体混合物的方法；以及使用光学分离剂对醇进行光学分离的方法。在化学式中，R1至R10分别表示氢原子等；R11表示烷基等；R12表示碳氢基团等；R13表示碳氢基团等；A表示乙酰基等。
• Photoinduced Nitroarenes as Versatile Anaerobic Oxidants for Accessing Carbonyl and Imine Derivatives
  作者：Joshua K. Mitchell、Waseem A. Hussain、Ajay H. Bansode、Ryan M. O’Connor、Dan E. Wise、Michael H. Choe、Marvin Parasram

  DOI：10.1021/acs.orglett.3c02292

  日期：2023.9.8

  Herein, we report a protocol for the anaerobic oxidation of alcohols, amines, aldehydes, and imines promoted by photoexcited nitroarenes. Mechanistic studies support the idea that photoexcited nitroarenes undergo double hydrogen atom transfer (HAT) steps with alcohols and amines to provide the respective ketone and imine products. In the presence of aldehydes and imines, successive HAT and oxygen atom

  在此，我们报告了光激发硝基芳烃促进醇、胺、醛和亚胺厌氧氧化的方案。机理研究支持光激发硝基芳烃与醇和胺经历双氢原子转移（HAT）步骤以提供各自的酮和亚胺产物的观点。在醛和亚胺存在的情况下，连续发生 HAT 和氧原子转移 (OAT) 事件，分别产生羧酸和酰胺。这种转变适用于连续光流设置，从而缩短了反应时间。
• Iron-catalyzed cascade C–C/C–O bond formation of 2,4-dienals with donor–acceptor cyclopropanes: access to functionalized hexahydrocyclopentapyrans
  作者：Manmath Mishra、Kshitiz Verma、Sonbidya Banerjee、Tharmalingam Punniyamurthy

  DOI：10.1039/d3cc06261a

  日期：——

  Iron-catalyzed cascade C–C and C–O bond formation of 2,4-dienals with donor–acceptor cyclopropanes (DACs) has been developed to furnish hexahydrocyclopentapyrans. Optically active DACs can be coupled stereospecifically (>97% ee). Chirality transfer, use of iron-catalysis and substrate scope are the salient practical features.

  铁催化的 2,4-二醛与供体-受体环丙烷 (DAC) 级联形成 C-C 和 C-O 键已被开发用于提供六氢环戊吡喃。光学活性 DAC 可以立体定向耦合 (>97% ee)。手性转移、铁催化的使用和底物范围是显着的实用特征。