2,5,6-三氯烟酸 | 54718-39-7

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 羧酸酐的卤化、磺化、硝化或硝化衍生物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2,5,6-三氯烟酸
• 英文名称: 2,5,6-Trichloronicotinic Acid
• 英文别名: 2,5,6-trichloropyridine-3-carboxylic acid
• CAS: 54718-39-7
• 化学式: C₆H₂Cl₃NO₂
• 分子量: 226.446
• InChiKey: XMJRZCYSCMZVJQ-UHFFFAOYSA-N

物化性质

• 熔点：
  158-161 °C
• 沸点：
  359.1±37.0 °C(Predicted)
• 密度：
  1.728

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335

制备方法与用途

用途

2,5,6-三氯烟酸可作为医药合成中间体。

制备

2,5,6-三氯烟酸可通过以下步骤制备：首先，以2-甲基戊二腈为原料制备3-甲基哌啶-2,6-二酮；接着进行氯代反应得到2,3,6-三氯-5-甲基吡啶；最后将甲基氧化即可得到2,5,6-三氯烟酸。

反应信息

• 作为反应物：
  描述：

  2,5,6-三氯烟酸 在 ammonium hydroxide 作用下， 生成 3-氯吡啶-2,6-二胺
  参考文献：
  名称：

  Synthesis and biological evaluation of aroylguanidines related to amiloride as inhibitors of the human platelet Na+/H+ exchanger

  摘要：

  Pyridine and benzene bioisosteres of amiloride were synthesized and evaluated for their inhibitory Potency against the sodium-hydrogen exchanger (NHE) involved in intracellular pH regulation. The inhibition of NHE was determined by using the platelet swelling assay (PSA) in which the swelling of human platelets was induced by their incubation in an acid buffer (pH 6.7). Additionally, the inhibitory potency of the most active compounds was assessed by measuring the inhibition of the EIPA-sensitive Na-22 (+) uptake (UIA) by human platelets after intracellular acidosis. The results indicated that several benzene derivatives and compounds bearing an carbonylguanidine moiety in the meta position of the pyridine nitrogen were much more potent than amiloride (PSA:IC50 = 43.5 muM, UIA:IC50 = 100.1 muM), but less than EIPA, a pyrazine NHE inhibitor (PSA:IC50=0.08 muM, UIA: IC50 - 0.5 muM). In both biological assays (2-amino-5-bromo-pyridine-3-carbonyl)guanidine (32) was the most active molecule (PSA: IC50 = 0.8 muM, UIA : IC50 = 0.8 muM). Our investigations demonstrated that the replacement of the pyrazine ring of amiloride e by a pyridine ora phenyl ring improved the NHE inhibitory potency (phenyl >pyridine >pyrazine). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00022-6
• 作为产物：
  描述：

  3-甲基环戊烷-1,2-二胺 在 盐酸 、 potassium permanganate 、 五氯化磷 、 硫酸 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 48.0h， 生成 2,5,6-三氯烟酸
  参考文献：
  名称：

  In vitro and in vivo evaluation of 6-aminopyrazolyl-pyridine-3-carbonitriles as JAK2 kinase inhibitors

  摘要：

  Synthesis and biological evaluation of a series of 6-aminopyrazolyl-pyridine-3-carbonitriles as JAK2 kinase inhibitors was reported. Biochemical screening, followed by profile optimization, resulted in JAK2 inhibitors exhibiting good kinase selectivity, pharmacokinetic properties, physical properties and pharmacodynamic effects. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.053

文献信息

• 2-methoxyimino-2-(pyridinyloxymethyl)phenyl acetamides with carboxylic
  申请人：Dow AgroSciences LLC

  公开号：US05968875A1

  公开（公告）日：1999-10-19

  The present invention provides novel 2-methoximino-2-(pyridinyloxymethyl)phenyl acetamide compounds with carboxylic acid substituents on the pyridine ring, their use as fungicidal compounds, and their use in fungicidal compositions comprising at least one of the 2-methoximino-2-(pyridinyloxymethyl)phenyl acetamide compounds as the active ingredient.

  本发明提供了在吡啶环上具有羧酸取代基的新型2-甲氧基亚胺基-2-(吡啶氧甲基)苯乙酰胺化合物，其作为杀真菌化合物的用途，以及它们在包含至少一种2-甲氧基亚胺基-2-(吡啶氧甲基)苯乙酰胺化合物作为活性成分的杀真菌组合物中的用途。
• [EN] COMPOUNDS TARGETING RNA-BINDING PROTEINS OR RNA-MODIFYING PROTEINS<br/>[FR] COMPOSÉS CIBLANT DES PROTÉINES DE LIAISON À L'ARN OU DES PROTÉINES MODIFIANT L'ARN
  申请人：TWENTYEIGHT SEVEN INC

  公开号：WO2021178420A1

  公开（公告）日：2021-09-10

  The invention relates to a compound represented by Formula (I): or a pharmaceutically acceptable salt thereof, compositions comprising the same and methods of preparing and using the same. The variables are described herein.

  该发明涉及由化学式（I）表示的化合物，或其药用可接受盐，包括含有该化合物的组合物以及制备和使用该化合物的方法。这里描述了变量。
• Small Molecule Inhibitors of KRAS G12C Mutant
  申请人：Merck Sharp & Dohme Corp.

  公开号：US20210122764A1

  公开（公告）日：2021-04-29

  The disclosure provides compounds of Formula (I) or a pharmaceutically acceptable salt thereof, wherein W 1 , W 2 , Y, Z, M, L, C y , C z , R 1 , R 2 , R 3 , R 4 , R 2a , R y , R z and the subscripts m, n, q, and r are as described herein. The compounds or their pharmaceutically acceptable salts can inhibit the G12C mutant of Kirsten rat sarcoma (KRAS) protein and are expected to have utility as therapeutic agents, for example, for treating cancer. The disclosure also provides pharmaceutical compositions which comprise compounds of Formula (I) or pharmaceutically acceptable salts thereof. The disclosure also relates to methods for use of the compounds or their pharmaceutically acceptable salts in the therapy and prophylaxis of cancer and for preparing pharmaceuticals for this purpose.

  该披露提供了Formula (I)的化合物或其药用盐，其中W1、W2、Y、Z、M、L、Cy、Cz、R1、R2、R3、R4、R2a、Ry、Rz以及下标m、n、q和r如本文所述。这些化合物或其药用盐可以抑制Kirsten大鼠肉瘤（KRAS）蛋白的G12C突变体，并有望作为治疗剂具有用途，例如用于治疗癌症。该披露还提供了包含Formula (I)的化合物或其药用盐的药物组合物。该披露还涉及使用这些化合物或其药用盐在癌症的治疗和预防中的方法，以及为此目的制备药物。
• [EN] PD-1/PD-L1 INHIBITORS<br/>[FR] INHIBITEURS PD-1/PD-L1
  申请人：GILEAD SCIENCES INC

  公开号：WO2018195321A1

  公开（公告）日：2018-10-25

  Compounds according to formula (I), methods of using said compounds singly or in combination with additional agents and compositions of said compounds for the treatment of cancer are disclosed.

  根据公式（I）制备的化合物，以及使用这些化合物单独或与其他药剂结合的方法，以及用于治疗癌症的这些化合物的组合物被披露。
• KRAS G12C INHIBITORS AND METHODS OF USING THE SAME
  申请人：AMGEN INC.

  公开号：US20180177767A1

  公开（公告）日：2018-06-28

  Provided herein are KRAS G12C inhibitors, composition of the same, and methods of using the same. These inhibitors are useful for treating a number of disorders, including pancreatic, colorectal, and lung cancers.

  本文提供了KRAS G12C抑制剂，其组成，以及使用方法。这些抑制剂对治疗多种疾病有用，包括胰腺癌、结直肠癌和肺癌。