2-(3-iodophenyl)acetyl chloride | 127109-66-4

• 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: 2-(3-iodophenyl)acetyl chloride
• 英文别名: 3-Iodophenylacetic acid chloride
• CAS: 127109-66-4
• 化学式: C₈H₆ClIO
• 分子量: 280.493
• InChiKey: ZJEGTAPQVAMXCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(3-iodophenyl)acetyl chloride 在 三氯化铝 、 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 生成
  参考文献：
  名称：

  Benzoquinazoline inhibitors of thymidylate synthase: enzyme inhibitory activity and cytotoxicity of some 3-amino- and 3-methylbenzo[f]quinazolin-1(2H)-ones

  摘要：

  The synthesis and thymidylate synthase (TS) inhibitory activity of a series of simple benzo-[f]-quinazolin-1(2H)-ones are described. Fully aromatic 3-amino compounds with compact lipophilic substituents in the 9-position were found to have I50 values as low as 20 nM on the isolated enzyme, and represent the first examples of potent, folate-based TS inhibitors that completely lack any structural feature corresponding to the (p-aminobenzoyl)glutamate moiety of the cofactor. A number of the compounds also showed moderate growth inhibitory activity against a human colon adenocarcinoma cell line (SW480), with IC50 values as low as 2 muM.

  DOI：

  10.1021/jm00068a004
• 作为产物：
  描述：

  3-碘苯乙酸 在 N,N-二甲基甲酰胺 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-(3-iodophenyl)acetyl chloride
  参考文献：
  名称：

  从头并行设计，合成和评估针对人类免疫缺陷病毒1型和耐药变异体的逆转录酶的抑制剂。

  摘要：

  我们使用分子模型设计了针对人类免疫缺陷病毒1型（HIV-1）的野生型和逆转录酶（RT）的耐药变异的从头广泛抑制剂。首先，我们筛选了可与四个RT结构（一个野生型和三个突变体）中的每一个相互作用的小片段。然后，将这些片段连接以构建支架分子。在合成的27种不同化合物中，有4种抑制RT的DNA聚合酶活性，IC50值低于10 microM。化合物5f抑制RT的IC50值约为3.5 microM，同时比临床使用的药物奈韦拉平（11-环丙基-5,11-二氢-4-甲基-6H-二吡啶基[3， 2-b：2'，3'-e] [1,4] diazepin-6-ne）。5f还以20 microM的IC50抑制RT核糖核酸酶H的活性，因此，与奈韦拉平不同，5f靶向两种RT活性。因此，5f可以作为开发针对RT的新型抑制剂的先导，该抑制剂可用于抑制HIV-1的生长。

  DOI：

  10.1021/jm0613121

文献信息

• [EN] FUSED [1,2,4]THIADIAZINE DERIVATIVES WHICH ACT AS KAT INHIBITORS OF THE MYST FAMILY<br/>[FR] DÉRIVÉS DE [1,2,4]THIADIAZINE FUSIONNÉS AGISSANT EN TANT QU'INHIBITEURS DE KAT DE LA FAMILLE DES MYST
  申请人：CTXT PTY LTD

  公开号：WO2019043139A1

  公开（公告）日：2019-03-07

  A compound of formula (I): which inhibits the activity of one or more KATs of the MYST family, i.e., TIP60, KAT6B, MOZ, HBO1 and MOF.

  一种化合物的化学式（I）：抑制MYST家族中一个或多个KATs的活性，即TIP60、KAT6B、MOZ、HBO1和MOF。
• Inhibition of cholesterol side-chain cleavage. 3. 22-Azacholesterol analogs bearing aryl-substituted side chains
  作者：Norma G. Delaney、Matthias C. Lu

  DOI：10.1021/jm00141a003

  日期：1981.9

  potent inhibitory activity of 22-azacholesterol analogue 2a, in which the (3-methylbutyl)amino side chain had been replaced by the (phenylethyl)amino side chain, on the conversion of cholesterol to pregnenolone prompted the synthesis and enzymatic studies of two series of 22-azacholesterol analogues bearing (arylalkyl)amino and (arylalkyl)amino side chains. The potent inhibitory activity of both the amines

  22-氮杂胆固醇类似物2a的有效抑制活性，其中（3-甲基丁基）氨基侧链已被（苯乙基）氨基侧链取代，对胆固醇向孕烯醇酮的转化促进了两个系列的合成和酶学研究带有（芳烷基）氨基和（芳烷基）氨基侧链的22-氮杂胆固醇类似物的制备。胺（2）和酰胺（3）的强抑制活性都表明碱性氮不是抑制活性的必要条件。然而，其中羰基和氮的位置互换的酰胺类似物（4）是较差的抑制剂。芳香族环上的吸电子基团降低了苯乙酰胺基系列的抑制活性，而供电子基团的抑制作用则有所增加。
• Cobalt Catalyzed α-Hydroxylation of Arylacetic Acid Equivalents with Dioxygen
  作者：Rupali Dasharath Shinde、Anil Rajendra Paraskar、Jogendra Kumar、Eliza Ghosh、Tapan Kanti Paine、Sukalyan Bhadra

  DOI：10.1021/acs.joc.4c00708

  日期：2024.7.5

  A cobalt catalyst, under oxidative conditions, facilitates the single electron transfer process in N-pyridyl arylacetamides to form α-carbon-centered radicals that readily react with molecular oxygen, giving access to mandelic acid derivatives. In contrast to the known benzylic hydroxylation approaches, this approach enables chemo- and regioselective hydroxylation at a benzylic position adjacent to

  钴催化剂在氧化条件下促进N-吡啶基芳基乙酰胺中的单电子转移过程，形成易于与分子氧反应的 α-碳中心自由基，从而获得扁桃酸衍生物。与已知的苄基羟基化方法相比，该方法能够在与( N-吡啶基)酰胺相邻的苄基位置处进行化学和区域选择性羟基化。条件温和、适用范围广、选择性好、合成实用性广，奠定了该反应的优点。
• Optimizing Small Molecule Inhibitors of Calcium-Dependent Protein Kinase 1 to Prevent Infection by Toxoplasma gondii
  作者：Sebastian Lourido、Chao Zhang、Michael S. Lopez、Keliang Tang、Jennifer Barks、Qiuling Wang、Scott A. Wildman、Kevan M. Shokat、L. David Sibley

  DOI：10.1021/jm4001314

  日期：2013.4.11

  Toxoplasma gondii is sensitive to bulky pyrazolo [3,4-d] pyrimidine (PP) inhibitors due to the presence of a Gly gatekeeper in the essential calcium dependent protein kinase 1 (CDPK1). Here we synthesized a number of new derivatives of 3-methyl-benzyl-PP (3-MB-PP, or 1). The potency of PP analogues in inhibiting CDPK1 enzyme activity in vitro (low nM IC50 values) and blocking parasite growth in host cell monolayers in vivo (low mu M EC50 values) were highly correlated and occurred in a CDPK1-specific manner. Chemical modification of the PP scaffold to increase half-life in the presence of microsomes in vitro led to identification of compounds with enhanced stability while retaining activity. Several of these more potent compounds were able to prevent lethal infection with T. gondii in the mouse model. Collectively, the strategies outlined here provide a route for development of more effective compounds for treatment of toxoplasmosis and perhaps related parasitic diseases.
• Nonpeptide Inhibitors of Measles Virus Entry
  作者：Aiming Sun、Andrew Prussia、Weiqiang Zhan、Ernest E. Murray、Joshua Doyle、Li-Ting Cheng、Jeong-Joong Yoon、Eugene V. Radchenko、Vladimir A. Palyulin、Richard W. Compans、Dennis C. Liotta、Richard K. Plemper、James P. Snyder

  DOI：10.1021/jm0602559

  日期：2006.8.1

  Measles virus (MV) is one of the most infectious pathogens known. Despite the existence of a vaccine, over 500 000 deaths/year result from MV or associated complications. Anti-measles compounds could conceivably reverse these statistics. Previously, we described a homology model of the MV fusion protein trimer and a putative binding site near the head-neck region. The resulting model permitted the identification of two nonpeptidic entry inhibitors. Here, we present the design, synthesis, and bioevaluation of several series of fusion inhibitors and describe their structure-activity relationships (SAR). Five simply substituted anilides show low-mu M blockade of the MV, one of which (AS-48) exhibits IC50 0.6-3.0 mu M across a panel of wild-type MV strains found in the field. Molecular field topology analysis (MFTA), a 2D QSAR approach based on local molecular properties (atomic charges, hydrogen-bonding capacity and local lipophilicity), applied to the anilide series suggests structural modifications to improve potency.