6-bromo-2-methyl-2H-chromene-3-carbaldehyde | 1320210-90-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: 6-bromo-2-methyl-2H-chromene-3-carbaldehyde
• 英文别名: 3-formyl-2-methyl-6-bromo-2H-chromene；6-bromo-2-methyl-2H-chromene-3-carboxaldehyde
• CAS: 1320210-90-9
• 化学式: C₁₁H₉BrO₂
• 分子量: 253.095
• InChiKey: CEOKABCQKYHDKV-UHFFFAOYSA-N

物化性质

• 沸点：
  355.4±42.0 °C(Predicted)
• 密度：
  1.568±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-bromo-2-methyl-2H-chromene-3-carbaldehyde 在 4-二甲氨基吡啶 、 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 21.0h， 生成
  参考文献：
  名称：

  Structure–activity studies of (−)-epigallocatechin gallate derivatives as HCV entry inhibitors

  摘要：

  Preventing viral entry into cells is a recognized approach for HIV therapy and has attracted attention for use against the hepatitis C virus (HCV). Recent reports described the activity of (-)-epigallocatechin gallate (EGCG) as an inhibitor of HCV entry with modest potency. EGCG is a polyphenolic natural product with a wide range of biological activity and unfavorable pharmaceutical properties. In an attempt to identify more drug-like EGCG derivatives with improved efficacy as HCV entry inhibitors, we initiated structure-activity investigations using semi-synthetic and synthetic EGCG analogs. The data show that there are multiple regions in the EGCG structure that contribute to activity. The gallate ester portion of the molecule appears to be of particular importance as a 3,4-difluoro analog of EGCG enhanced potency. This derivative and other active compounds were shown not to be cytotoxic in Huh-7 cell culture. These data suggest that more potent, non-cytotoxic EGCG analogs can be prepared in an attempt to identify more drug-like candidates to treat HCV infection by this mechanism.

  DOI：

  10.1016/j.bmcl.2014.07.051
• 作为产物：
  描述：

  5-溴水杨醛 、 丁烯-2-醛 在 α -Amylase from Bacillus subtilis 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 48.0h， 以50%的产率得到6-bromo-2-methyl-2H-chromene-3-carbaldehyde
  参考文献：
  名称：

  Catalytical promiscuity of α-amylase: Synthesis of 3-substituted 2H-chromene derivatives via biocatalytic domino oxa-Michael/aldol condensations

  摘要：

  An facile and green one-pot route has been developed for the synthesis of chromenes using salicylaldehyde and alpha,beta-unsaturated ketones. alpha-Amylase from Bacillus subtilis shows excellent catalytic activity and exerts good adaptability to different substrates in the reaction. This promiscuous enzyme-catalyzed domino reaction not only extends the application of alpha-amylase from B. subtilis for new chemical transformations, but also provided an alternative synthetic method for 2H-chromene derivatives. (c) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2013.02.001

文献信息

• A novel NHC-catalyzed transformation of 2H-chromene-3-carboxaldehydes to 3-methyl-2H-chromen-2-ones
  作者：Vijay Nair、C. R. Sinu、R. Rejithamol、K. C. Seetha Lakshmi、Eringathodi Suresh

  DOI：10.1039/c1ob05325f

  日期：——

  An unexpected transformation of 2H-chromene-3-carboxaldehydes to coumarin derivatives, mediated by NHC, is reported.

  报告了在 NHC 介导下，2H-Chromene-3-carboxaldehydes 向香豆素衍生物的意外转化。
• Design and Metal-Free Synthesis and Cytotoxicity Evaluation of 5Hchromeno[ 4,3-b]pyridine Derivatives as Anti-Proliferative Agents
  作者：M. Sayaji Rao、Basi Venkata Subba Reddy、Kamalaker Reddy Kamireddy、Rajashaker Bantu、Sunil Misra、Balasubramanian Sridhar

  DOI：10.2174/1570178619666220415231814

  日期：2023.2

  A novel metal-free approach is reported for the synthesis of 5H-chromeno[4,3-b]pyridine derivatives. Indeed, chromene derivatives are found to exhibit a broad spectrum of biological activities such as antibacterial, antirhinovirus, antioxidant, cytotoxic, anticancer, and antimicrobial properties.

  This method provides an easy access to a large number of 5H-chromeno[4,3-b]pyridine scaffolds by the condensation of 3-formylchromene with -enaminoesters under thermal conditions. All compounds are well characterized by NMR, IR and mass spectrometry. This is a safe and convenient protocol.

  Thus newly synthesized compounds are evaluated for their cytotoxicity against four human cancer cell lines, such as B16 (Skin cancer), DU145 (Prostate cancer), Hela (Cervical cancer) and CHO (Chinese hamster ovary).

  Among them, compounds 3n and 3o shows an excellent anti-proliferation activity against CHO (IC50 12.33+1.13 μM), Hela (IC50 22.33+0.51 μM), and B16 (IC50 27.61+0.8 μM) cell lines, while compounds 3c, 3g and 3q exhibits promising anti-proliferation against above four human cancer cell lines with IC50 14.96+1.9, 15.59+0.9, 13.8+0.06 μM, respectively, compared with a standard drug Doxorubicin & Mitomycin.

  背景：报告了一种合成 5H-色烯并[4,3-b]吡啶衍生物的新型无金属方法。事实上，色烯衍生物具有广泛的生物活性，如抗菌、抗鼻病毒、抗氧化、细胞毒性、抗癌和抗微生物特性。

  方法：该方法通过 3-甲酰基色烯与 -enaminoesters 在热条件下缩合，可方便地获得大量 5H-色烯并[4,3-b]吡啶支架。所有化合物均通过核磁共振、红外光谱和质谱法进行了表征。这是一种安全方便的方法。 结果：新合成的化合物对四种人类癌症细胞系，如 B16（皮肤癌）、DU145（前列腺癌）、Hela（宫颈癌）和 CHO（中国仓鼠卵巢癌）的细胞毒性进行了评估。 结论：其中，化合物3n和3o对CHO（IC50 12.33+1.13 μM）、Hela（IC50 22.33+0.51 μM）和B16（IC50 27.61+0.而化合物 3c、3g 和 3q 与标准药物多柔比星& 丝裂霉素相比，对上述四种人类癌症细胞株的抗增殖作用分别为 IC50 14.96+1.9、15.59+0.9、13.8+0.06 μM。
• 2H-chromene derivatives bearing thiazolidine-2,4-dione, rhodanine or hydantoin moieties as potential anticancer agents
  作者：Mohammad Azizmohammadi、Mehdi Khoobi、Ali Ramazani、Saeed Emami、Abdolhossein Zarrin、Omidreza Firuzi、Ramin Miri、Abbas Shafiee

  DOI：10.1016/j.ejmech.2012.10.044

  日期：2013.1

  A variety of (Z)-[(2H-chromen-3-yl)methylene]azolidinones 6a-t bearing thiazolidine-2,4-dione, rhodanine or hydantoin scaffolds were designed and synthesized as potential anticancer agents. Inhibitory effect of synthesized compounds 6a-t on the viability of cancer and non-cancer cells was assessed using MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) reduction assay. The SAR study revealed that the N-substitution of azolidinone moiety cannot improve the activity but S/NH replacement (thiazolidine-2,4-dione/hydantoin) and S/O alteration (rhodanine/thiazolidine-2,4-dione) enable us to modulate the growth inhibition activity against various cell lines. Moreover, 6-bromo and 2-methyl substituents on chromene ring had positive effects on growth inhibitory activity depending on the tumor cell lines. Among the synthesized compounds, hydantoin derivative 60 with a 6-bromo-2-methyl-2H-chromene substructure showed the best profile of cytotoxicity comparable to that of cisplatin as standard anticancer agent. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Catalytical promiscuity of α-amylase: Synthesis of 3-substituted 2H-chromene derivatives via biocatalytic domino oxa-Michael/aldol condensations
  作者：Long-Hua Zhou、Na Wang、Wei Zhang、Zong-Bo Xie、Xiao-Qi Yu

  DOI：10.1016/j.molcatb.2013.02.001

  日期：2013.7

  An facile and green one-pot route has been developed for the synthesis of chromenes using salicylaldehyde and alpha,beta-unsaturated ketones. alpha-Amylase from Bacillus subtilis shows excellent catalytic activity and exerts good adaptability to different substrates in the reaction. This promiscuous enzyme-catalyzed domino reaction not only extends the application of alpha-amylase from B. subtilis for new chemical transformations, but also provided an alternative synthetic method for 2H-chromene derivatives. (c) 2013 Elsevier B.V. All rights reserved.
• Structure–activity studies of (−)-epigallocatechin gallate derivatives as HCV entry inhibitors
  作者：Rohit Bhat、Amna T. Adam、Jungeun Jasmine Lee、Gaspard Deloison、Yves Rouillé、Karin Séron、David P. Rotella

  DOI：10.1016/j.bmcl.2014.07.051

  日期：2014.9

  Preventing viral entry into cells is a recognized approach for HIV therapy and has attracted attention for use against the hepatitis C virus (HCV). Recent reports described the activity of (-)-epigallocatechin gallate (EGCG) as an inhibitor of HCV entry with modest potency. EGCG is a polyphenolic natural product with a wide range of biological activity and unfavorable pharmaceutical properties. In an attempt to identify more drug-like EGCG derivatives with improved efficacy as HCV entry inhibitors, we initiated structure-activity investigations using semi-synthetic and synthetic EGCG analogs. The data show that there are multiple regions in the EGCG structure that contribute to activity. The gallate ester portion of the molecule appears to be of particular importance as a 3,4-difluoro analog of EGCG enhanced potency. This derivative and other active compounds were shown not to be cytotoxic in Huh-7 cell culture. These data suggest that more potent, non-cytotoxic EGCG analogs can be prepared in an attempt to identify more drug-like candidates to treat HCV infection by this mechanism.