N-(3-formylphenyl)benzamide | 123926-68-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(3-formylphenyl)benzamide
• 英文别名: 3-Benzoylaminobenzaldehyde
• CAS: 123926-68-1
• 化学式: C₁₄H₁₁NO₂
• 分子量: 225.247
• InChiKey: QVPNAQHWDZRJIS-UHFFFAOYSA-N

物化性质

• 熔点：
  116-117 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  303.1±25.0 °C(Predicted)
• 密度：
  1.251±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(3-formylphenyl)benzamide 在 air 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 邻二氯苯 为溶剂， 140.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 以74%的产率得到7-formyl-2-phenylbenzoxazole
  参考文献：
  名称：

  Copper-Catalyzed Synthesis of Benzoxazoles via a Regioselective C−H Functionalization/C−O Bond Formation under an Air Atmosphere

  摘要：

  An efficient method for the synthesis of functionalized benzoxazoles is described that involves a copper(II)-catalyzed regioselective C-H functionalization/C-O bond formation protocol. The use of dichlorobenzene as a solvent at 160 degrees C allows the use of air as the tern-final oxidant in the catalytic synthesis of benzoxazoles in a process that has high functional group tolerance. The presence of a directing group at the meta position markedly improves the reaction efficacy and a variety of 7-substituted benzoxazoles are selectively produced under mild reaction conditions. The mechanism of the reaction is also discussed in this report.

  DOI：

  10.1021/jo900513z
• 作为产物：
  描述：

  1-(二乙氧基甲基)-3-硝基苯 在 sodium sulfide 、 sodium hydroxide 、 sodium hydrogensulfide 、 乙醇 作用下， 生成 N-(3-formylphenyl)benzamide
  参考文献：
  名称：

  Haworth; Lapworth, Journal of the Chemical Society, 1922, vol. 121, p. 83

  摘要：

  DOI：

文献信息

• Synthesis and biological evaluation of novel synthetic chalcone derivatives as anti-tumor agents targeting Cat L and Cat K
  作者：Yali Wang、Situ Xue、Ruolan Li、Zhihui Zheng、Hong Yi、Zhuorong Li

  DOI：10.1016/j.bmc.2017.09.019

  日期：2018.1

  A series of chalcone derivatives bearing benzamide or benzenesulfonamide moieties were synthesized and evaluated for their anti-tumor effect on HCT116, MCF7 and 143B cell lines in vitro. SAR analysis showed that compounds bearing a benzenesulfonamide group had greater potency than those bearing a benzamide group. It was also shown that compounds with a mono-methyl or mono-halogen group at the 3-position

  合成了一系列带有苯甲酰胺或苯磺酰胺部分的查耳酮衍生物，并评价了它们对HCT116，MCF7和143B细胞系的体外抗肿瘤作用。SAR分析表明，带有苯磺酰胺基团的化合物比带有苯甲酰胺基团的化合物具有更高的效价。还显示在末端苯环的3-位具有单甲基或单卤素基团的化合物比具有三氟甲基或甲氧基的化合物更有效。化合物8e对HCT116，MCF7和143B细胞系表现出最强的抗肿瘤活性，IC 50值分别为0.597、0.886和0.791μM。分子对接研究和酶促测定表明，化合物8e的抗肿瘤活性可能受Cat L和Cat K调控。
• Photo‐Induced Construction of <i>N</i> ‐Aryl Amides by Fe Catalysis
  作者：Yong‐Kang Mei、Xiang‐Ting Min、Shi‐Yu Guo、Chang‐Hui Liu、Xiang‐Xin Zhang、Ding‐Wei Ji、Boshun Wan、Qing‐An Chen

  DOI：10.1002/ejoc.202200043

  日期：2022.4.12

  Inspired by recent transition-metal catalyzed electrophilic amidations, we developed a photo-induced electrophilic amidation of arylboronic acids with Fe catalyst to construct C−N bond. This protocol is also featured by its mild condition and broad substrate scope.

  受最近过渡金属催化的亲电酰胺化的启发，我们开发了芳基硼酸与 Fe 催化剂的光诱导亲电酰胺化以构建 C-N 键。该协议还具有条件温和、底物范围广的特点。
• Design and synthesis of novel benzoxazole analogs as Aurora B kinase inhibitors
  作者：Ying An、Eun Lee、Yeongji Yu、Jieun Yun、Myeong Youl Lee、Jong Soon Kang、Woo-Young Kim、Raok Jeon

  DOI：10.1016/j.bmcl.2016.05.017

  日期：2016.7

  A novel series of benzoxazole analogs was designed and synthesized, and their inhibitory activities against Aurora kinases were evaluated. Some of the tested compounds exhibited a promising activity with respect to the inhibition of Aurora B kinase. A structure-activity relationship study indicated that linker length, regiochemistry, and halogen substitution play important roles in kinase inhibitory

  设计并合成了一系列新颖的苯并恶唑类似物，并评估了其对极光激酶的抑制活性。一些测试的化合物在抑制Aurora B激酶方面显示出有希望的活性。构效关系研究表明，接头长度，区域化学和卤素取代在激酶抑制效能中起重要作用。通过分子对接研究解释了代表性化合物与Aurora激酶之间的结合模式，以解释对Aurora A和B激酶的抑制活性和选择性。化合物13l和13q也以剂量依赖的方式对人肿瘤细胞系显示抗增殖作用。最有效的13q在前列腺癌PC-3肿瘤异种移植模型中显示出良好的疗效。
• [EN] PYRAZOLO[4,3-D]PYRIMIDINES AS KINASE INHIBITORS<br/>[FR] PYRAZOLO[4,3-D]PYRIMIDINES UTILES EN TANT QU'INHIBITEURS DE KINASES
  申请人：ORIGENIS GMBH

  公开号：WO2014060112A1

  公开（公告）日：2014-04-24

  The present invention relates to novel compounds of formula (I) that are capable of inhibiting one or more kinases, especially SYK (Spleen Tyrosine Kinase), LRRK2 (Leucine-rich repeat kinase 2) and/or MYLK (Myosin light chain kinase) or mutants thereof. The compounds find applications in the treatment of a variety of diseases. These diseases include autoimmune diseases, inflammatory diseases, bone diseases, metabolic diseases, neurological and neurodegenerative diseases, cancer, cardiovascular diseases, allergies, asthma, alzheimer's disease, parkinson's disease, skin disorders, eye diseases, infectious diseases and hormone-related diseases.

  本发明涉及具有式（I）的新化合物，其能够抑制一个或多个激酶，特别是SYK（脾酪氨酸激酶）、LRRK2（富含亮氨酸重复的激酶2）和/或MYLK（肌球蛋白轻链激酶）或其突变体。这些化合物可用于治疗多种疾病。这些疾病包括自身免疫疾病、炎症性疾病、骨疾病、代谢性疾病、神经和神经退行性疾病、癌症、心血管疾病、过敏、哮喘、阿尔茨海默病、帕金森病、皮肤疾病、眼部疾病、传染病和激素相关疾病。
• Substituted alkylamine derivatives
  申请人：Banyu Pharmaceutical Co., Ltd.

  公开号：US05234946A1

  公开（公告）日：1993-08-10

  The substituted alkylamine derivatives represented by formula (I) ##STR1## wherein R.sup.1 represents (a) substituted or unsubstituted C.sub.2-6 alkenyl group, (b) substituted or unsubstituted C.sub.3-6 cycloalkenyl group, (c) substituted or unsubstituted C.sub.2-6 alkynyl group, (d) substituted or unsubstituted aryl group, (e) substituted or unsubstituted heterocyclic group, (f) fused heterocyclic group which may be substituted, or (g) group represented by the formula Ru.sup.11 -Ar wherein R.sup.11 is a heterocyclic group and Ar is a 5- or 6-membered aromatic ring which may contain a hetero N, O or S atom, and which may be substituted; ##STR2## represents a 5- or 6-membered aromatic ring which may contain a hetero N, O or S atom, and may be substituted by R.sup.7, X and Y are linking groups, R.sup.2 is H or lower alkyl, R.sup.3 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl or lower cycloalkyl, R.sup.4 and R.sup.5 are independently hydrogen or halogen atoms, R.sup.6 represents (a) substituted or unsubstituted acyclic hydrocarbon group which may be unsaturated, (b) substituted or unsubstituted cycloalkyl group, or (c) substituted or unsubstituted phenyl group, or non-toxic salts thereof. (E)-N-(6-6-dimethyl-2-hepten-4-ynyl)-N-ethyl-3-[4-(3-thienyl)-2-thienyl-me thyloxy]benzylamine hydrochloride is a representative example. The substituted alkylamine derivatives are useful as pharmaceuticals, particularly for the treatment and prevention of hypercholesterolemia, hyperlipemia and arteriosclerosis.

  公式（I）所代表的取代基烷基胺衍生物，其中R1代表（a）取代或未取代的C2-6烯丙基基团，（b）取代或未取代的C3-6环烯基基团，（c）取代或未取代的C2-6炔基基团，（d）取代或未取代的芳基基团，（e）取代或未取代的杂环基团，（f）可能被取代的融合杂环基团，或（g）由Ru11-Ar表示的基团，其中R11是杂环基团，Ar是5-或6-成员芳香环，可以含有杂原子N、O或S，且可以被取代；表示5-或6-成员芳香环，可以含有杂原子N、O或S，可以被R7取代，X和Y是连接基团，R2是H或较低的烷基，R3是氢、较低的烷基、较低的烯丙基、较低的炔基或较低的环烷基，R4和R5独立地表示氢或卤素原子，R6表示（a）取代或未取代的非环烷基，可以不饱和，（b）取代或未取代的环烷基，或（c）取代或未取代的苯基，或其非毒性盐。 （E）-N-（6-6-二甲基-2-庚烯-4-炔基）-N-乙基-3- [4-（3-噻吩基）-2-噻吩基]甲氧基]苯基胺盐酸盐是一个代表性的例子。这些取代基烷基胺衍生物可用作药物，特别是用于治疗和预防高胆固醇血症、高脂血症和动脉硬化。