6-chloro-chroman-4-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-chloro-chroman-4-ol
• 英文别名: 6-chloro-3,4-dihydro-2H-1-benzopyran-4-ol；6-chloro-3,4-dihydro-2H-chromen-4-ol
• 化学式: C₉H₉ClO₂
• 分子量: 184.622
• InChiKey: DTXFWMLTXBVKIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-chloro-chroman-4-ol 在 盐酸 、 硫酸 、 水 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 72.33h， 生成 N-[6-chlorochroman-4-yl]-N'-(3-nitrophenyl)thiourea
  参考文献：
  名称：

  N-Aryl-N′-(chroman-4-yl)ureas and thioureas display in vitro anticancer activity and selectivity on apoptosis-resistant glioblastoma cells: Screening, synthesis of simplified derivatives, and structure–activity relationship analysis

  摘要：

  A series of chroman derivatives previously reported as potassium channel openers, as well as some newly synthesized simplified structures, were examined for their in vitro effects on the growth of three human high-grade glioma cell lines: U373, T98G, and Hs683. Significant in vitro growth inhibitory activity was observed with 2,2-dimethylchroman-type nitro-substituted phenylthioureas, such as compounds 4o and 4p. Interestingly, most tested phenylureas were found to be slightly less active, but more cell selective (normal versus tumor glial cells, such as 3d, 3e, and 3g), thus less toxic, than the corresponding phenylthioureas. No significant differences were observed in terms of chroman-derivative-induced growth inhibitory effects between glioma cells sensitive to pro-apoptotic stimuli (Hs683 glioma cells) and glioma cells associated with various levels of resistance to pro-apoptotic stimuli (U373 and T98G glioma cells), a feature that suggests non-apoptotic-mediated growth inhibition. Flow cytometry analyses confirmed the absence of pro-apoptotic effects for phenylthioureas and phenylureas when analyzed in U373 glioma cells and demonstrated U373 cell cycle arrest in the G0/G1 phase. Computer-assisted phase-contrast videomicroscopy revealed that 3d and 3g displayed cytostatic effects, while 3e displayed cytotoxic ones. As a result, this work identified phenylurea-type 2,2-dimethylchromans as a new class of antitumor agents to be further explored for an innovative therapeutic approach for high-grade glioma and/or for a possible new mechanism of action. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.050
• 作为产物：
  描述：

  6-氯-4-二氢色原酮 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 6-chloro-chroman-4-ol
  参考文献：
  名称：

  R2NSO2DPEN-（CH2）n（η6-芳基）共轭配体的ansa-钌（II）配合物，用于芳基酮的不对称转移加氢

  摘要：

  新3次代设计师柄-钌（II）络合物配Ñ，Ç -亚烷基-拴系的Ñ，Ñ -dialkylsulfamoyl-DPEN /η 6个-arene配体，在各种类的不对称转移氢化（ATH）显示出良好的催化性能甲酸/三乙胺混合物中的（杂）芳基酮。特别是，在低催化剂负载下，苯并稠合的环状酮可提供98至99.9％ee的ee。

  DOI：

  10.1002/adsc.201500288

文献信息

• [EN] AMINOMETHYL-BIARYL DERIVATIVES AS COMPLEMENT FACTOR D INHIBITORS AND USES THEREOF<br/>[FR] DÉRIVÉS D'AMINOMÉTHYL-BIARYL EN TANT QU'INHIBITEURS DU FACTEUR D DU COMPLÉMENT ET LEURS UTILISATIONS
  申请人：NOVARTIS AG

  公开号：WO2015009977A1

  公开（公告）日：2015-01-22

  The present invention provides a compound of formula (I), a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.

  本发明提供了一种公式(I)的化合物，一种制造本发明化合物的方法及其治疗用途。本发明进一步提供了一种药物活性剂的组合物和一种药物组合物。
• Syntheses of 4-Aryl Chromanes: A Rearrangement Approach
  作者：Pailla Umareddy、Arava Veera Reddy、L. K. Ravindranath

  DOI：10.1080/00397911.2015.1015140

  日期：2015.5.19

  Abstract 4-Aryl chromanes are synthesized from 4-Aryloxy chromanes via a rearrangement methodology. GRAPHICAL ABSTRACT

  摘要 4-芳基色满由4-芳氧基色满通过重排方法合成。图形概要
• [EN] INHIBITORS OF COMPLEMENT FACTORS AND USES THEREOF<br/>[FR] INHIBITEURS DE FACTEURS DU COMPLÉMENT ET LEURS UTILISATIONS
  申请人：ANNEXON INC

  公开号：WO2022020244A1

  公开（公告）日：2022-01-27

  Disclosed are compounds of formula I and II and pharmaceutically acceptable salts thereof. Also disclosed are methods of treating a neurodegenerative disorder, an inflammatory disease, an autoimmune disease, an ophthalmic disease or a metabolic disorder using the compounds disclosed herein.

  揭示了式I和II的化合物及其药用盐。还披露了使用此处披露的化合物治疗神经退行性疾病、炎症性疾病、自身免疫疾病、眼科疾病或代谢性疾病的方法。
• Production of enantiopure chiral aryl heteroaryl carbinols using whole‐cell <i>Lactobacillus paracasei</i> biotransformation
  作者：Engin Şahin

  DOI：10.1080/00397911.2019.1707226

  日期：2020.2.16

  the first example for an enantiopure production of (S)-6-chlorochroman-4-ol (3a), which has many antioxidant activity, by a biological method. For asymmetric bioreduction of other prochiral ketones, these results open way to use of L. paracasei BD87E6 as biocatalysts. Also, the present process shows a hopeful and alternative green synthesis for the production of enantiopure carbinols in a mild, inexpensive

  摘要 芳基和杂芳基手性甲醇是药物合成中有用的前体。从谷物发酵饮料中获得的副干酪乳杆菌 BD87E6 被研究作为全细胞生物催化剂，用于将不同的酮（包括芳香族、杂芳香族和稠合双环酮）生物还原为手性甲醇，可用作药物中间体. 该研究表明，芳基、杂芳基和稠合双环酮 (1-5) 以优异的对映选择性 (>99%) 和高产率生物还原为其相应的手性甲醇 (1a-5a)。本研究给出了第一个通过生物方法生产具有多种抗氧化活性的 (S)-6-chlorochroman-4-ol (3a) 对映体纯的例子。对于其他前手性酮的不对称生物还原，这些结果为使用 L. 副干酪 BD87E6 作为生物催化剂。此外，本方法显示了一种以温和、廉价和环境友好的方法生产对映纯甲醇的有希望和替代的绿色合成方法。图形概要
• Aminomethyl-Biaryl Derivatives Complement Factor D inhibitors and uses thereof
  申请人：BELANGER David B.

  公开号：US20160145247A1

  公开（公告）日：2016-05-26

  The present invention provides a compound of formula (I), a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.

  本发明提供了一种公式（I）的化合物，一种制造本发明化合物的方法及其治疗用途。本发明还提供了一种药理活性剂的组合物和制药组合物。