6,8-dichloro-2-phenyl-2H-chromene-3-carboxaldehyde | 1228538-80-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 6,8-dichloro-2-phenyl-2H-chromene-3-carboxaldehyde
• 英文别名: 6,8-dichloro-2-phenyl-2H-chromene-3-carbaldehyde
• CAS: 1228538-80-4
• 化学式: C₁₆H₁₀Cl₂O₂
• 分子量: 305.16
• InChiKey: VJDFHGZSEVYDGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  6,8-dichloro-2-phenyl-2H-chromene-3-carboxaldehyde 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (6,8-dichloro-2-phenyl-2H-chromen-3-yl)methanol
  参考文献：
  名称：

  Synthesis of function-oriented 2-phenyl-2H-chromene derivatives using l-pipecolinic acid and substituted guanidine organocatalysts

  摘要：

  Organocatalytic domino oxa-Michael/aldol reactions between salicylaldehyde with electron deficient olefins are presented. We screened guanidine, 1,1,3,3-tetramethylguanidine (TMG) and L-pipecolinic acid as organocatalysts for this transformation. 3-Substituted 2-phenyl-2H-chromene derivatives are synthesized with high yields and with poor enantioselectivity (5-17% ee) using L-pipecolinic acid while TMG works well with cinnamaldehyde without using co-catalyst. These 3-substituted-2-phenyl-2H-chromene derivatives are further derivatized to synthesize triazole and biotin-containing chromene derivatives, to facilitate purification of protein targets. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.143
• 作为产物：
  描述：

  肉桂醛 、 3,5-二氯水杨醛 在 四氢吡咯 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以85%的产率得到6,8-dichloro-2-phenyl-2H-chromene-3-carboxaldehyde
  参考文献：
  名称：

  （Z / E）-2-苯基/ H -3-styryl-2 H-色烯衍生物作为抗微管剂的设计与合成

  摘要：

  摘要合成了两个新的化合物系列（Z  /  E）-2-苯基/ H -3-苯乙烯基-2 H - Chromenes 9（a - r）和10（a - s），并评估了其对四种癌细胞的体外细胞毒活性线。在HeLa细胞系中，一种化合物（Z）-8-乙氧基-3-（4-甲氧基苯乙烯基）-2-苯基-2H-色烯（ 9g）是测试化合物中活性最高的化合物（\（{\ hbox {IC}} _​​ {50} 10 {\ upmu} \ hbox {M} \））。复方9g 在G2 / M期捕获细胞，破坏微管网络，在可溶性级分中积累微管蛋白，并显示G2 / M标记物Cyclin B1的表达增加。 图形概要概要两个新系列的化合物（Ž  /  é）-2-苯基/ ħ -3-苯乙烯基- 2 ħ -Chromenes（37个的化合物）的合成和评价体外细胞毒性对四名癌细胞系活性。在HeLa细胞系中，一种化合物（Z）-8-乙氧基-3-（

  DOI：

  10.1007/s12039-018-1520-6

文献信息

• Diastereoselective synthesis of novel spiro indanone fused pyrano[3,2-<i>c</i>]chromene derivatives following hetero-Diels–Alder reaction and<i>in vitro</i>anticancer studies
  作者：Pravati Panda、Sabita Nayak、Susanta Ku. Sahoo、Seetaram Mohapatra、Deepika Nayak、Rajalaxmi Pradhan、Chanakya Nath Kundu

  DOI：10.1039/c8ra02729c

  日期：——

  development of concise methods for the synthesis of small functionalised spirocyclic molecules is important in the search of new bioactive molecules. To contribute this, here we represent a diastereoselective oxa-hetero-Diels–Alder reaction for the synthesis of novel spiro indanone fused pyrano[3,2-c]chromene derivatives and studied their in vitro anticancer activities. Using previously less explored cyclic

  开发用于合成小的功能化螺环分子的简明方法对于寻找新的生物活性分子很重要。为此，我们在这里代表了一种非对映选择性氧杂-杂-Diels-Alder 反应，用于合成新型螺茚满酮稠合吡喃并[3,2- c ]色烯衍生物，并研究了它们的体外抗癌活性。使用以前较少探索的环酮，即茚满-1,3-二酮和3-乙烯基-2 H-色烯衍生物，我们在“类药物”分子和天然产物之间的界面处获得了新型螺杂环骨架。各种螺茚满酮稠合吡喃[3,2- c在 120 °C 回流条件下，使用 4 Å MS 作为添加剂，在甲苯中以高产率（高达 85%）合成了具有四元立体中心的 ]色烯衍生物，具有优异的非对映选择性。这些化合物对 MCF-7（乳腺癌）、HCT-116（结肠癌）、H-357（口腔癌）、MD-MB-231（乳腺癌）细胞系的体外细胞毒性研究通过 MTT 3- (4,5-二甲基噻唑-2-基)-2,5-二苯基溴化四唑}体外测定。筛选结果显示，与商业抗癌药物
• [EN] LKB1-AMPK ACTIVATORS FOR THERAPEUTIC USE IN POLYCYSTIC KIDNEY DISEASE<br/>[FR] ACTIVATEURS DE L'AMPK DE LKB1 POUR UNE UTILISATION THÉRAPEUTIQUE DANS LA POLYKYSTOSE RÉNALE
  申请人：UNIV KANSAS

  公开号：WO2016073470A1

  公开（公告）日：2016-05-12

  Compounds are provided for use in treating polycystic kidney disease (PKD) and in associated methods that include a method of modulating (e.g., activating) Liver kinase Bl (LKBI); and a method of modulating (e.g., decreasing activity) mammalian target of rapamycin (mTOR). The methods may include introducing the compound in a therapeutically effective amount to a subject having PKD. The methods may include introducing the compound in a therapeutically effective amount to a subject having Autosomal Dominant PKD. The compounds can be used in methods of treating a disease modulated by a mTOR pathway, which can include introducing the compound in a therapeutically effective amount to a subject having the disease modulated by the mTOR pathway. The disease modulated by mTOR is selected from the group consisting of multiple types of cancer, leukemia, kidney disease, obesity, neuro disorders and alcohol-related chronic diseases.

  提供用于治疗多囊肾病（PKD）的化合物，以及相关方法，包括调节（例如激活）肝激酶Bl（LKBI）的方法；以及调节（例如降低活性）哺乳动物雷帕霉素靶蛋白（mTOR）的方法。这些方法可能包括向患有PKD的受试者引入治疗有效量的化合物。这些方法可能包括向患有常染色体显性PKD的受试者引入治疗有效量的化合物。这些化合物可用于治疗由mTOR途径调节的疾病的方法，其中可以包括向患有由mTOR途径调节的疾病的受试者引入治疗有效量的化合物。由mTOR调节的疾病可从包括多种癌症、白血病、肾脏疾病、肥胖、神经障碍和与酒精相关的慢性疾病在内的一组中选择。
• Design and Synthesis of (&lt;i&gt;E&lt;/i&gt;)-4-(2-Phenyl-2&lt;i&gt;H&lt;/i&gt;-chromen-3-yl)but-3-en-2-ones and Evaluation of their &lt;i&gt;In Vitro&lt;/i&gt; Antimicrobial Activity
  作者：Sabita Nayak、Subhendu Chakroborty、Sujitlal Bhakta、Pravati Panda、Seetaram Mohapatra、Sanjeet Kumar、Padan Jena、Chandrasekhar Purohit

  DOI：10.2174/1570178612666150331204016

  日期：2015.5.9

  2H-Chromene and its derivatives are an important class of organic compounds due to their wide range of biological activities such as antimicrobial, antiviral, antiimflamatory and antitubercular agents. In the present work we have synthesized ten new 2H-chromene derivatives [(E)-4-(2-phenyl- 2H-chromen-3-yl)but-3-en-2-one and its substituted analogues] following aldol condensation of 2Hchromene- 3-carbaldehydes with acetone. These products have been characterized by means of spectral data (1H, 13C, IR, Mass). The structure of one new compound (E)-4-(6,8-dichloro-2-phenyl-2H-chromen-3-yl)but-3-en-2- one was confirmed by X-ray analysis and the product was subsequently subjected to the in vitro evaluation of antimicrobial activity against two Gram positive bacteria Streptococcus mutans (MTCC 497) and Streptococcus pyogenes (MTCC 1926) and three Gram negative bacteria Vibrio cholera (MTCC 3909), Shigella flexneri (MTCC 1457) and Salmonella enteric typhi (MTCC 1252). The obtained results from in vitro antimicrobial assays by broth dilution method indicated that many compounds under study exhibited excellent activity against all the microorganisms in comparison to standard kanamycin.

  2H-香烯及其衍生物是一类重要的有机化合物，因为它们具有广泛的生物活性，如抗微生物、抗病毒、抗炎和抗结核作用。在本研究中，我们合成了十种新的2H-香烯衍生物[(E)-4-(2-苯基-2H-香烯-3-基)丁-3-烯-2-酮及其取代类似物]，该过程通过将2H-香烯-3-醛与丙酮进行醇脱水缩合反应而得到。这些产物通过光谱数据（1H、13C、红外、质谱）进行了表征。通过X射线分析确认了一种新化合物(E)-4-(6,8-二氯-2-苯基-2H-香烯-3-基)丁-3-烯-2-酮的结构，随后该产物进行了体外抗微生物活性评估，针对两种革兰氏阳性细菌链球菌变种（MTCC 497）和化脓性链球菌（MTCC 1926），以及三种革兰氏阴性细菌霍乱弧菌（MTCC 3909）、志贺氏菌（MTCC 1457）和沙门氏菌（MTCC 1252）。通过肉汤稀释法进行的体外抗微生物实验结果表明，许多研究中的化合物与标准卡那霉素相比，对所有微生物表现出优良的活性。
• [EN] HCK INHIBITORS FOR THE TREATMENT OF FIBROSIS AND CANCER<br/>[FR] INHIBITEURS DE HCK POUR LE TRAITEMENT DE LA FIBROSE ET DU CANCER
  申请人：ICAHN SCHOOL MED MOUNT SINAI

  公开号：WO2020205921A1

  公开（公告）日：2020-10-08

  Compounds which are thiazole and triazole derivatives are disclosed, including compounds of the following genus: Formula I. The compounds are inhibitors of hematopoietic cell kinase (HCK) and exhibit anti-fibrotic and anti-proliferative effects. They are useful in the treatment of a variety of disorders, including a fibrosis or a fibrotic disease, such as renal fibrosis.

  本发明揭示了噻唑和三唑衍生物的化合物，包括以下属的化合物：化学式I。这些化合物是造血细胞激酶（HCK）的抑制剂，具有抗纤维化和抗增殖作用。它们在治疗各种疾病中很有用，包括纤维化或纤维化疾病，如肾脏纤维化。
• Development of a New Methodology for Dearomative Borylation of Coumarins and Chromenes and Its Applications to Synthesize Boron-Containing Retinoids
  作者：Bhaskar C. Das、Pratik Yadav、Sasmita Das、Mariko Saito、Todd Evans

  DOI：10.3390/molecules28031052

  日期：——

  coumarins and chromenes via conjugate addition represents a relatively unexplored and challenging task. To address this issue, herein, we report a new and general copper (I) catalyzed dearomative borylation process to synthesize boron-containing oxacycles. In this report, the borylation of coumarins, chromones, and chromenes comprising functional groups, such as esters, nitriles, carbonyls, and amides, has

  通过共轭加成对香豆素和色烯进行脱芳香硼化是一项相对未经探索且具有挑战性的任务。为了解决这个问题，我们在此报告了一种新的通用铜（I）催化脱芳硼化工艺来合成含硼氧杂环化合物。在本报告中，已经实现了包含酯、腈、羰基和酰胺等官能团的香豆素、色酮和色烯的硼基化。此外，该方法还生成不同类别的潜在硼基类维生素A，包括具有恶二唑和花青素基序的类维生素A。硼酸化的氧杂环化合物可以作为合适的中间体来生成化合物库。