methyl 2-isothiocyanato-5-methoxybenzoate | 344333-11-5

• 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: methyl 2-isothiocyanato-5-methoxybenzoate
• CAS: 344333-11-5
• 化学式: C₁₀H₉NO₃S
• 分子量: 223.252
• InChiKey: XPGBFGXRTGNRTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.22
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  47.89
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 2-isothiocyanato-5-methoxybenzoate 在 sodium hydrosulfide hydrate 、 potassium tert-butylate 、 二异丁基氢化铝 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.5h， 生成
  参考文献：
  名称：

  一种抗肿瘤化合物及其合成方法与应用

  摘要：

  本发明属于药物化学领域，具体涉及一种抗肿瘤化合物及其合成方法与应用。所述化合物具有通式I或通式II所示结构，对蛋白酶体调节激酶DYRK2展现出很好的抑制活性，进而可以通过抑制蛋白酶体达成抗肿瘤活性。本发明还涉及所述化合物的合成方法，该方法采用化学全合成路线，这种汇聚式的合成路线可应用于类似结构化合物及相关衍生物的化学合成，为新型抗肿瘤药物开辟了广阔发展空间。

  公开号：

  CN110981803B
• 作为产物：
  描述：

  methyl 2-formylamino-5-methoxybenzoate 在 selenium 、 sulfur 、 三氯氧磷 作用下， 生成 methyl 2-isothiocyanato-5-methoxybenzoate
  参考文献：
  名称：

  One-pot synthesis of 4-substituted 4-alkoxy-1,4-dihydro-3,1-benzoxazine-2-thiones by the reaction of 2-isothiocyanatobenzoates with organolithiums

  摘要：

  An efficient one-pot procedure for the preparation of 4-substituted 4-alkoxy-1,4-dihydro-3,1-benzoxazine-2-thiones from 2-isothiocyanatobenzoates has been developed. Thus, 2-isothiocyanatobenzoates were reacted with organolithiums including lithium enolates of acetates and tertiary acetamides in THF at -78 degrees C to give the desired products in generally good yields. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.088

文献信息

• Identification of Novel Fused Heteroaromatics-Based MALT1 Inhibitors by High-Throughput Screening to Treat B Cell Lymphoma
  作者：Xuewu Liang、Chenxia Sun、Chunpu Li、Haolan Yu、Xiaohui Wei、Xuyi Liu、Wei Bao、Yuqiang Shi、Xiaochen Sun、Mirzadavlat Khamrakulov、Chenghua Yang、Hong Liu

  DOI：10.1021/acs.jmedchem.1c00466

  日期：2021.7.8

  lymphoid tissue lymphoma translocation protein 1 (MALT1) inhibitors is of great value and significance in the treatment of neoplastic disorders and inflammatory and autoimmune diseases. However, there is a lack of effective MALT1 inhibitors in clinic. Herein, a novel class of potent 5-oxo-1-thioxo-4,5-dihydro-1H-thiazolo[3,4-a]quinazoline-based MALT1 inhibitors and their covalent derivatives were first identified

  黏膜相关淋巴组织淋巴瘤易位蛋白 1 (MALT1) 抑制剂的开发在肿瘤性疾病、炎症和自身免疫性疾病的治疗中具有重要价值和意义。然而，临床上缺乏有效的MALT1抑制剂。在此，首次通过高通量鉴定和设计了一类新型有效的 5-oxo-1-thioxo-4,5-dihydro-1 H - thiazolo[3,4- a ]quinazoline 抑制剂及其共价衍生物。筛选。我们证明了化合物15c、15e和20c有效抑制 MALT1 蛋白酶并对活化的 B 细胞样弥漫性大 B 细胞淋巴瘤具有低个位数微摩尔效力显示出选择性细胞毒性。此外，化合物20c以剂量依赖性方式特异性抑制 MALT1 依赖性 TMD8 细胞中的 NF-κB 信号传导并诱导细胞凋亡。更重要的是，20c在 TMD8 异种移植肿瘤模型中显示出良好的药代动力学特性和抗肿瘤功效，且无显着毒性。总的来说，这项研究为 MALT1 抑制剂的进一步结构
• ANT-LIGANDS MOLECULES AND BIOLOGICAL APPLICATIONS
  申请人：Borgne-Sanchez Annie

  公开号：US20110086865A1

  公开（公告）日：2011-04-14

  The invention relates to molecules ANT-ligands having a substituted nitrogeneous heterocycle A wherein —A is a substituted pyrazinone of formula I wherein R1 is —(CH 2 ) n —CO—OH; —(CH 2 ) n —CO—OR; —(CH 2 ) n —CO—NHR; —(CH 2 ) n —CO—N(R, R′); —(CH 2 ) n —OH; —(CH 2 ) n —OR; —(CH 2 ) n —OAr; —(CH 2 ) n —C(R,R′) —(CH 2 ) n —OH, R and R′, in the above radicals, being identical or different and representing H or a C1-C12 alkyl or cycloalkyl radical; and Ar is a phenyl or Het., Het. representing an heterocyclic radical with one or several hetero atoms selected between N, S and O, said phenyl or heterocycle being optionally substituted by one or several atoms, groups or radicals selected from halogen atoms such as Cl, Br, I, or halogenated groups such as —CCl 3 or —CF 3 ; one or several —OH, —OR, —COOH or —COOR groups; a phenyl; a linear or branched C1-C12 alkyl radical; —NH—COR; or —CN; said groups occupying the same or different positions on the phenyl or heterocyclic radical; a linear or branched C1-C12 alkyl radical; a linear or branched C2-C12 alkylene radical; —(CH 2 ) n —C3-C6 cycloalkyl radical; —(CH 2 ) n Ar or —(CH 2 ) n Het.; —(CH 2 ) n —NH—CO—R; —(CH 2 ) n —NH 2 ; —(CH 2 ) n —N(R,R′); —(CH 2 ) n —NH—CO—OH; —(CH 2 ) n —NH—CO—OR; —NH—(CH 2 ) n —CO—OH; —NH—(CH 2 ) n —CO—OR; R2 is —(CH 2 ) n -Ar, Ar being such as above defined and being optionally substituted such as above defined; a linear or branched C1-C12 alkyl or C2-C12 alkylene radical with one or several double bonds; —(CH 2 ) n —OH; —(CH 2 ) n —OR; —(CH 2 ) n —CO—Het; —(CH 2 ) n —NH—CO—R; —(CH 2 ) n —NH 2 ; —(CH 2 ) n —N(R,R′); —(CH 2 ) n —CO—OH; —(CH 2 ) n —CO—OR; a linear or branched C1-C12 alkyl radical; —(CH 2 ) n —C(R)=CH—C (R)=CH 2 , R3 forms a phenyl or an heterocyclic condensed group with the two adjacent carbons of the pyrazinone residue, said condensed group being optionally substituted such as above defined for Ar and Het.; and/or condensed to a cyclohexyl or oxanyl group, in turn optionally substituted such as above defined for Ar; n is 0 or an integer from 1 to 5; or A is a substituted pyrazine of formula II wherein R 4 is a —CO—NH—Ar radical, optionally substituted such as above defined; R5 forms a phenyl or heterocyclic group condensed to the two adjacent carbon groups of the pyrazine residue, said phenyl or heterocyclic group being optionally substituted such as above defined, and Ar being such as above defined with respect to formula I or A is a substituted pyridine group of formula III wherein, Ar and R2 are as above defined with respect to formula I.

  该发明涉及具有取代氮杂环A的分子ANT配体，其中—A是具有以下式I的取代吡嗪酮：其中R1是—(CH2)n—CO—OH;—( )n—CO—OR;—( )n—CO—NHR;—( )n—CO—N(R, R′);—( )n—OH;—( )n—OR;—( )n—OAr;—( )n—C(R,R′)—( )n—OH，上述基团中的R和R′相同或不同，代表H或C1-C12烷基或环烷基基团；Ar是苯基或Het.，Het.代表一个杂原子为N、S和O的杂环基团，所述苯基或杂环基团可以选择性地被一个或多个原子、基团或基团取代，所选基团包括卤原子如Cl、Br、I，或卤代基团如—CCl3或—CF3；一个或多个—OH、—OR、—COOH或—COOR基团；苯基；线性或支链的C1-C12烷基基团；—NH—COR；或—CN；这些基团可以占据苯基或杂环基团上的相同或不同位置；线性或支链的C1-C12烷基基团；线性或支链的C2-C12亚烯基基团；—( )n—C3-C6环烷基基团；—( )nAr或—( )nHet.；—( )n—NH—CO—R；—( )n—NH2；—( )n—N(R,R′)；—( )n—NH—CO—OH；—( )n—NH—CO—OR；—NH—( )n—CO—OH；—NH—( )n—CO—OR；R2是—( )n-Ar，Ar如上定义，可以选择性地被如上定义取代；线性或支链的C1-C12烷基或C2-C12亚烯基基团，带有一个或多个双键；—( )n—OH；—( )n—OR；—( )n—CO—Het；—( )n—NH—CO—R；—( )n—NH2；—( )n—N(R,R′)；—( )n—CO—OH；—( )n—CO—OR；线性或支链的C1-C12烷基基团；—( )n—C(R)=CH—C(R)= ；R3形成一个苯基或与吡嗪酮残基的两个相邻碳原子形成杂环的紧凑基团，所述紧凑基团可以选择性地被如上定义的Ar和Het取代；和/或紧凑为一个环己基或氧杂环基团，进一步可以选择性地被如上定义的Ar取代；n为0或1到5的整数；或A是具有以下式II的取代吡嗪：其中R4是一个—CO—NH—Ar基团，可以选择性地被如上定义取代；R5形成一个苯基或杂环基团，紧凑到吡嗪残基的两个相邻碳基团，所述苯基或杂环基团可以选择性地被如上定义取代，Ar如上定义，关于式I的定义；或A是具有以下式III的取代吡啶基团：其中，Ar和R2如上定义，关于式I的定义。
• KIENZLE, F.;KAISER, A.;MINDER, R. E., HELV. CHIM. ACTA, 1983, 66, N 1, 148-157
  作者：KIENZLE, F.、KAISER, A.、MINDER, R. E.

  DOI：——

  日期：——