9H-咔唑-1-甲酸 | 6311-19-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 9H-咔唑-1-甲酸
• 英文名称: 9H-carbazole-1-carboxylic acid
• 英文别名: carbazole-1-carboxylic acid；Carbazol-1-carbonsaeure；Carbazol-carbonsaeure-(1)
• CAS: 6311-19-9
• 化学式: C₁₃H₉NO₂
• mdl: MFCD00957625
• 分子量: 211.22
• InChiKey: DHHFGQADZVYGIE-UHFFFAOYSA-N

物化性质

• 熔点：
  271-272 °C
• 沸点：
  497.2±18.0 °C(Predicted)
• 密度：
  1.422±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9H-咔唑-1-甲酸 在 sodium hydroxide 、 dipotassium hydrogenphosphate 、 potassium dihydrogenphosphate 、 葡萄糖 、 Pseudomonas aeruginosa 、 magnesium sulfate 、 potassium nitrate 、 sodium chloride 、 calcium chloride 作用下， 以 水 为溶剂， 反应 72.0h， 以75%的产率得到咔唑
  参考文献：
  名称：

  Chakraborty; Chowdhury, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 6, p. 617 - 620

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl carbazole-1-carboxylate 生成 9H-咔唑-1-甲酸
  参考文献：
  名称：

  135.邻苯二甲腈对四氢咔唑进行脱氢

  摘要：

  DOI：

  10.1039/jr9450000530

文献信息

• NOVEL CARBAZOLE EHOP-016 DERIVATIVES AS ANTI-CANCER AND ANTI-MIGRATORY AGENTS
  申请人：UNIVERSITY OF PUERTO RICO

  公开号：US20190125746A1

  公开（公告）日：2019-05-02

  A series of novel of EHop-016 derivatives is presented herein via designing and synthesizing compounds that mimics its more favorable “U-shaped” conformation that appears to be critical for inhibitory activity against Rac. Based on modeling studies on EHop-016, compounds with a more rigid structural conformation can mimic this “U-shaped” conformation would improve the anti-migration activity against metastatic cells. Compounds are disclosed that inhibit RhoGTPases that are useful for inhibiting hyperprofilerative and neoplastic diseases. Specifically, the compounds inhibit the GTPases Rac and Cdc42 that are overactive or overexpressed in signaling pathways in cancer and metastasis. Methods for treatment of cancer and hyperproliferative diseases are disclosed.

  本文介绍了一系列EHop-016衍生物，通过设计和合成模拟其更有利的“U”形构象的化合物，这对于抑制Rac的活性至关重要。基于对EHop-016的建模研究，具有更严格结构构象的化合物可以模拟这种“U”形构象，从而提高对转移性细胞的抗迁移活性。披露了抑制对抗过度增殖和肿瘤性疾病有用的RhoGTP酶的化合物。具体来说，这些化合物抑制了在癌症和转移中信号通路中过度活跃或过度表达的Rac和Cdc42 GTP酶。还披露了治疗癌症和过度增殖性疾病的方法。
• A tautomeric ligand enables directed C‒H hydroxylation with molecular oxygen
  作者：Zhen Li、Zhen Wang、Nikita Chekshin、Shaoqun Qian、Jennifer X. Qiao、Peter T. Cheng、Kap-Sun Yeung、William R. Ewing、Jin-Quan Yu

  DOI：10.1126/science.abg2362

  日期：2021.6.25

  challenging when oxygen is used as the oxidant. Here, we report a palladium complex bearing a bidentate pyridine/pyridone ligand that efficiently catalyzes this reaction at ring positions adjacent to carboxylic acids. Infrared, x-ray, and computational analysis support a possible role of ligand tautomerization from mono-anionic (L,X) to neutral (L,L) coordination in the catalytic cycle of aerobic carbon–hydrogen

  当使用氧气作为氧化剂时，使用过渡金属催化剂对芳基碳氢键进行羟基化已被证明具有挑战性。在这里，我们报告了一种钯配合物，它带有双齿吡啶/吡啶酮配体，可在与羧酸相邻的环位置有效地催化该反应。红外、X 射线和计算分析支持从单阴离子 (L,X) 到中性 (L,L) 配位的配体互变异构在好氧碳氢羟基化反应的催化循环中的可能作用。由杂环决定的传统位点选择性被这种催化剂推翻，从而允许在以前无法接近的位点对药物感兴趣的化合物进行后期修饰。
• Amide compounds
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US06770667B1

  公开（公告）日：2004-08-03

  The present invention is a compound and pharmaceutical composition comprising a compound of formula (I): wherein R1 is a 4-(lower) alkyl-imidazol-1-yl or a 4,5-di(lower) alkyl-imidazol-1-yl group, R2 is a hydrogen atom or a lower alkyl group, and R3 is a fluorenyl group. The compound of formula (I) includes pharmaceutically acceptable salts: The compound of formula (I) and salts thereof have 5-HT antagonism activity.

  本发明是一种化合物和药物组合物，包括式(I)的化合物：其中R1是4-(较低)烷基-咪唑-1-基或4,5-二(较低)烷基-咪唑-1-基基团，R2是氢原子或较低烷基基团，R3是芴基团。式(I)的化合物包括药用可接受的盐：式(I)的化合物及其盐具有5-HT拮抗活性。
• Potential antitumor agents. 54. Chromophore requirements for in vivo antitumor activity among the general class of linear tricyclic carboxamides
  作者：Brian D. Palmer、Gordon W. Rewcastle、Graham J. Atwell、Bruce C. Baguley、William A. Denny

  DOI：10.1021/jm00399a003

  日期：1988.4

  thioxanthenone, anthraquinone, pyridoquinazoline, dibenzodioxin, thianthrene, phenothiazine, phenoxazine, dibenzofuran, carbazole, and pyridoindole) of the general class of N-[2-(dimethylamino)ethyl] linear tricyclic carboxamides. Only the compounds containing coplanar chromophores intercalated DNA. There is an absolute requirement for an oxygen or aromatic nitrogen (possibly as hydrogen-bond acceptors) peri to

  报道了一般结构的许多不同实例（ac啶，吩嗪，蒽，a啶、,吨酮，噻吨酮，蒽醌，吡啶并喹唑啉，二苯并二恶英，噻吨，吩噻嗪，吩恶嗪，二苯并呋喃，咔唑和吡啶基吲哚的结构-抗肿瘤活性关系。 N- [2-（二甲基氨基）乙基]线性三环羧酰胺。仅包含共面发色团的化合物插入DNA。绝对需要羧酰胺周围的氧或芳族氮（可能是氢键受体），以及用于生物活性的平面环几何形状。除了进一步描述这类化合物的药效基团的性质外，该工作还确定了二苯并[1,4]二恶英是一种具有体内抗肿瘤活性的新型DNA嵌入发色团。
• [EN] CARBAZOLE CARBOXAMIDE COMPOUNDS USEFUL AS KINASE INHIBITORS<br/>[FR] COMPOSÉS DE CARBAZOLE-CARBOXAMIDE UTILES COMME INHIBITEURS DE KINASES
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2014210087A1

  公开（公告）日：2014-12-31

  Disclosed are compounds of Formula (I); and salts thereof, wherein:Formula (II); Q is: R1 is -C(CH3)2OH, -NHC(=0)C(CH3)3, -N(CH3)2, or -CH2Rd; R2 is CI or -CH3; R3 is H, F, or -CH3; Ra is H or -CH3; Rb is H, F, CI, or -OCH3 Rc is H or F; and Rd is -OH, -OCH3, -NHC(=0)CH3, or fORMULA (III), Also disclosed are methods of using such compounds as inhibitors of Bruton's tyrosine kinase (Btk), and pharmaceutical compositions comprising such compounds. These compounds are useful in treating, preventing, or slowing the progression of diseases or disorders in a variety of therapeutic areas, such as autoimmune diseases and vascular disease.

  公开了Formula (I)的化合物及其盐，其中：Formula (II)；Q是：R1为-C(CH3)2OH，-NHC(=0)C(CH3)3，-N(CH3)2，或-CH2Rd；R2为CI或-CH3；R3为H，F或-CH3；Ra为H或-CH3；Rb为H，F，CI或-OCH3；Rc为H或F；Rd为-OH，-OCH3，-NHC(=0)CH3，或Formula (III)。还公开了使用这些化合物作为Bruton酪氨酸激酶（Btk）抑制剂的方法，以及包含这些化合物的药物组合物。这些化合物在治疗、预防或减缓各种治疗领域的疾病或障碍方面具有用途，如自身免疫疾病和血管疾病。